NP-MRD: Showing NP-Card for Yanuthone D (NP0003480)

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Record Information

Version

1.0

Created at

2020-12-09 00:43:07 UTC

Updated at

2021-07-15 16:46:31 UTC

NP-MRD ID

NP0003480

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Yanuthone D

Provided By

NPAtlas

Description

5-{[(1S)-2,5-dioxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]Hept-3-en-3-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Yanuthone D is found in Aspergillus niger. It was first documented in 2000 (PMID: 11031048). Based on a literature review very few articles have been published on 5-{[(1S)-2,5-dioxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]Hept-3-en-3-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117473D          

 74 75  0  0  0  0            999 V2000
    9.4599    0.8889   -2.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4751    0.6761   -1.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7597    0.5184   -0.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3427    0.6205   -0.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2918    0.4094    0.7820 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6568   -0.8515    1.2342 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2466   -1.0629    0.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9051   -1.2341   -0.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2659   -1.1598    1.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8698   -1.3679    1.2971 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0794   -0.1937    1.8391 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6256   -0.2976    1.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -1.4760    1.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0170    0.6093    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2644    0.8575    0.2130 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5174    0.1322    0.2363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6157   -1.1775   -0.3023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -0.8460    0.9310 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6763   -0.6495    1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4248   -1.6490    1.1063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2896    0.6679    0.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4438    1.0760    1.7552 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6058    0.3096    1.5138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1977    0.2204    0.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6510    0.8566   -0.6640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4187   -0.5812   -0.0010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.7929   -0.4302   -1.4486 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7029   -0.8964   -2.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8853   -1.3141   -1.6913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2794    0.9381   -1.7392 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.4922    1.3237   -0.9900 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0900    0.5189   -0.2448 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0313    2.6087   -1.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6895    1.5199    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5622    0.9634   -0.5873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3701    1.1052   -1.8116 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3929    1.3749   -3.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3181   -0.0773   -3.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6142    1.5488   -3.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9184    1.3533    0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6086    0.4857   -1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7521   -0.4323   -0.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4244    0.7602   -1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3636    0.4618    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8368    1.3202    1.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7111   -0.8830    2.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2616   -1.7039    0.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8185   -1.4578   -1.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3731   -0.4076   -1.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3039   -2.1880   -0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5324   -1.0802    2.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5356   -2.3290    1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7469   -1.4749    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1440   -0.2357    2.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577    0.7229    1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083   -2.0797    1.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6102   -2.2025    2.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -1.2262    2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951    1.4532    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955    1.0958   -0.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5885    1.9699    0.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356   -1.5206    1.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6848    2.1338    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2518    1.0298    2.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2099   -1.6805    0.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2385   -0.3375    0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0705   -1.6271   -1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0653   -0.0710   -2.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1757   -1.3399   -3.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9057   -1.4240   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5030    1.7349   -1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5893    0.9373   -2.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6752    3.2346   -1.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0174    2.5281   -0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  1  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 21 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 18 16  1  0  0  0  0
 35 16  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  3 40  1  0  0  0  0
  3 41  1  0  0  0  0
  3 42  1  0  0  0  0
  4 43  1  0  0  0  0
  5 44  1  0  0  0  0
  5 45  1  0  0  0  0
  6 46  1  0  0  0  0
  6 47  1  0  0  0  0
  8 48  1  0  0  0  0
  8 49  1  0  0  0  0
  8 50  1  0  0  0  0
  9 51  1  0  0  0  0
 10 52  1  0  0  0  0
 10 53  1  0  0  0  0
 11 54  1  0  0  0  0
 11 55  1  0  0  0  0
 13 56  1  0  0  0  0
 13 57  1  0  0  0  0
 13 58  1  0  0  0  0
 14 59  1  0  0  0  0
 15 60  1  0  0  0  0
 15 61  1  0  0  0  0
 18 62  1  1  0  0  0
 22 63  1  0  0  0  0
 22 64  1  0  0  0  0
 26 65  1  0  0  0  0
 26 66  1  0  0  0  0
 28 67  1  0  0  0  0
 28 68  1  0  0  0  0
 28 69  1  0  0  0  0
 29 70  1  0  0  0  0
 30 71  1  0  0  0  0
 30 72  1  0  0  0  0
 33 73  1  0  0  0  0
 34 74  1  0  0  0  0
M  END

     RDKit          3D

 74 75  0  0  0  0  0  0  0  0999 V2000
    9.4599    0.8889   -2.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4751    0.6761   -1.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7597    0.5184   -0.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3427    0.6205   -0.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2918    0.4094    0.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6568   -0.8515    1.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2466   -1.0629    0.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9051   -1.2341   -0.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2659   -1.1598    1.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8698   -1.3679    1.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0794   -0.1937    1.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6256   -0.2976    1.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -1.4760    1.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0170    0.6093    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2644    0.8575    0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5174    0.1322    0.2363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6157   -1.1775   -0.3023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -0.8460    0.9310 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6763   -0.6495    1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4248   -1.6490    1.1063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2896    0.6679    0.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4438    1.0760    1.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6058    0.3096    1.5138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1977    0.2204    0.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6510    0.8566   -0.6640 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.0313    2.6087   -1.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5622    0.9634   -0.5873 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3181   -0.0773   -3.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6142    1.5488   -3.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9184    1.3533    0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6086    0.4857   -1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7521   -0.4323   -0.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4244    0.7602   -1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3636    0.4618    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8368    1.3202    1.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7111   -0.8830    2.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2616   -1.7039    0.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8185   -1.4578   -1.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3731   -0.4076   -1.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7951    1.4532    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.1757   -1.3399   -3.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9057   -1.4240   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5030    1.7349   -1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5893    0.9373   -2.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6752    3.2346   -1.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0174    2.5281   -0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
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  7  9  2  0
  9 10  1  0
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 14 15  1  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
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 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  1
 27 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 21 34  2  0
 34 35  1  0
 35 36  2  0
 18 16  1  0
 35 16  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  8 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
 10 52  1  0
 10 53  1  0
 11 54  1  0
 11 55  1  0
 13 56  1  0
 13 57  1  0
 13 58  1  0
 14 59  1  0
 15 60  1  0
 15 61  1  0
 18 62  1  1
 22 63  1  0
 22 64  1  0
 26 65  1  0
 26 66  1  0
 28 67  1  0
 28 68  1  0
 28 69  1  0
 29 70  1  0
 30 71  1  0
 30 72  1  0
 33 73  1  0
 34 74  1  0
M  END


  Mrv1652306242117473D          

 74 75  0  0  0  0            999 V2000
    9.4599    0.8889   -2.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4751    0.6761   -1.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7597    0.5184   -0.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3427    0.6205   -0.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2918    0.4094    0.7820 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6568   -0.8515    1.2342 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2466   -1.0629    0.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9051   -1.2341   -0.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2659   -1.1598    1.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8698   -1.3679    1.2971 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0794   -0.1937    1.8391 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6256   -0.2976    1.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -1.4760    1.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0170    0.6093    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2644    0.8575    0.2130 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5174    0.1322    0.2363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6157   -1.1775   -0.3023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -0.8460    0.9310 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6763   -0.6495    1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4248   -1.6490    1.1063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2896    0.6679    0.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4438    1.0760    1.7552 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6058    0.3096    1.5138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1977    0.2204    0.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6510    0.8566   -0.6640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4187   -0.5812   -0.0010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.7929   -0.4302   -1.4486 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7029   -0.8964   -2.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8853   -1.3141   -1.6913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2794    0.9381   -1.7392 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.4922    1.3237   -0.9900 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0900    0.5189   -0.2448 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0313    2.6087   -1.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6895    1.5199    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5622    0.9634   -0.5873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3701    1.1052   -1.8116 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3929    1.3749   -3.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3181   -0.0773   -3.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6142    1.5488   -3.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9184    1.3533    0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6086    0.4857   -1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7521   -0.4323   -0.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4244    0.7602   -1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3636    0.4618    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8368    1.3202    1.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7111   -0.8830    2.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2616   -1.7039    0.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8185   -1.4578   -1.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3731   -0.4076   -1.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3039   -2.1880   -0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5324   -1.0802    2.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5356   -2.3290    1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7469   -1.4749    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1440   -0.2357    2.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577    0.7229    1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083   -2.0797    1.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6102   -2.2025    2.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -1.2262    2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951    1.4532    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955    1.0958   -0.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5885    1.9699    0.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356   -1.5206    1.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6848    2.1338    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2518    1.0298    2.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2099   -1.6805    0.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2385   -0.3375    0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0705   -1.6271   -1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0653   -0.0710   -2.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1757   -1.3399   -3.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9057   -1.4240   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5030    1.7349   -1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5893    0.9373   -2.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6752    3.2346   -1.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0174    2.5281   -0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  1  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 21 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 18 16  1  0  0  0  0
 35 16  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  3 40  1  0  0  0  0
  3 41  1  0  0  0  0
  3 42  1  0  0  0  0
  4 43  1  0  0  0  0
  5 44  1  0  0  0  0
  5 45  1  0  0  0  0
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  6 47  1  0  0  0  0
  8 48  1  0  0  0  0
  8 49  1  0  0  0  0
  8 50  1  0  0  0  0
  9 51  1  0  0  0  0
 10 52  1  0  0  0  0
 10 53  1  0  0  0  0
 11 54  1  0  0  0  0
 11 55  1  0  0  0  0
 13 56  1  0  0  0  0
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 14 59  1  0  0  0  0
 15 60  1  0  0  0  0
 15 61  1  0  0  0  0
 18 62  1  1  0  0  0
 22 63  1  0  0  0  0
 22 64  1  0  0  0  0
 26 65  1  0  0  0  0
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 28 67  1  0  0  0  0
 28 68  1  0  0  0  0
 28 69  1  0  0  0  0
 29 70  1  0  0  0  0
 30 71  1  0  0  0  0
 30 72  1  0  0  0  0
 33 73  1  0  0  0  0
 34 74  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003480

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@@](O[H])(C([H])([H])[H])C([H])([H])C(=O)OC([H])([H])C1=C([H])C(=O)[C@@]2(O[C@]2([H])C1=O)C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O8/c1-18(2)8-6-9-19(3)10-7-11-20(4)12-13-28-22(29)14-21(25(33)26(28)36-28)17-35-24(32)16-27(5,34)15-23(30)31/h8,10,12,14,26,34H,6-7,9,11,13,15-17H2,1-5H3,(H,30,31)/b19-10+,20-12+/t26-,27+,28+/m1/s1

> <INCHI_KEY>
NIBXHVDVUJEQPO-OFWAVEGMSA-N

> <FORMULA>
C28H38O8

> <MOLECULAR_WEIGHT>
502.604

> <EXACT_MASS>
502.256668184

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.553690985137

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-5-{[(1S,6R)-2,5-dioxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
4.474234818666666

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.802693181989245

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8934820507732035

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0083987734509385

> <JCHEM_POLAR_SURFACE_AREA>
130.5

> <JCHEM_REFRACTIVITY>
137.34549999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-5-{[(1S,6R)-2,5-dioxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 74 75  0  0  0  0  0  0  0  0999 V2000
    9.4599    0.8889   -2.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4751    0.6761   -1.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7597    0.5184   -0.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3427    0.6205   -0.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2918    0.4094    0.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6568   -0.8515    1.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2466   -1.0629    0.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9051   -1.2341   -0.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2659   -1.1598    1.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8698   -1.3679    1.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0794   -0.1937    1.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6256   -0.2976    1.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -1.4760    1.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0170    0.6093    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2644    0.8575    0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5174    0.1322    0.2363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6157   -1.1775   -0.3023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -0.8460    0.9310 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6763   -0.6495    1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4248   -1.6490    1.1063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2896    0.6679    0.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4438    1.0760    1.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6058    0.3096    1.5138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1977    0.2204    0.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6510    0.8566   -0.6640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4187   -0.5812   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7929   -0.4302   -1.4486 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7029   -0.8964   -2.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8853   -1.3141   -1.6913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2794    0.9381   -1.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4922    1.3237   -0.9900 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0900    0.5189   -0.2448 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0313    2.6087   -1.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6895    1.5199    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5622    0.9634   -0.5873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3701    1.1052   -1.8116 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3929    1.3749   -3.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3181   -0.0773   -3.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6142    1.5488   -3.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9184    1.3533    0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6086    0.4857   -1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7521   -0.4323   -0.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4244    0.7602   -1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3636    0.4618    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8368    1.3202    1.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7111   -0.8830    2.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2616   -1.7039    0.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8185   -1.4578   -1.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3731   -0.4076   -1.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3039   -2.1880   -0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5324   -1.0802    2.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5356   -2.3290    1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7469   -1.4749    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1440   -0.2357    2.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577    0.7229    1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083   -2.0797    1.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6102   -2.2025    2.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -1.2262    2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951    1.4532    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955    1.0958   -0.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5885    1.9699    0.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356   -1.5206    1.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6848    2.1338    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2518    1.0298    2.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2099   -1.6805    0.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2385   -0.3375    0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0705   -1.6271   -1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0653   -0.0710   -2.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1757   -1.3399   -3.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9057   -1.4240   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5030    1.7349   -1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5893    0.9373   -2.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6752    3.2346   -1.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0174    2.5281   -0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  1
 27 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 21 34  2  0
 34 35  1  0
 35 36  2  0
 18 16  1  0
 35 16  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  8 48  1  0
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 29 70  1  0
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 30 72  1  0
 33 73  1  0
 34 74  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       9.460   0.889  -2.820  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.475   0.676  -1.366  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.760   0.518  -0.641  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.343   0.621  -0.679  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.292   0.409   0.782  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.657  -0.852   1.234  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.247  -1.063   0.829  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.905  -1.234  -0.605  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.266  -1.160   1.719  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.870  -1.368   1.297  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.079  -0.194   1.839  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.626  -0.298   1.461  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.879  -1.476   1.937  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.017   0.609   0.746  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.264   0.858   0.213  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.517   0.132   0.236  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.616  -1.178  -0.302  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.173  -0.846   0.931  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.676  -0.650   1.008  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.425  -1.649   1.106  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.290   0.668   0.974  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.444   1.076   1.755  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.606   0.310   1.514  0.00  0.00           O+0
HETATM   24  C   UNK     0      -7.198   0.220   0.261  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.651   0.857  -0.664  0.00  0.00           O+0
HETATM   26  C   UNK     0      -8.419  -0.581  -0.001  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.793  -0.430  -1.449  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.703  -0.896  -2.374  0.00  0.00           C+0
HETATM   29  O   UNK     0      -9.885  -1.314  -1.691  0.00  0.00           O+0
HETATM   30  C   UNK     0      -9.279   0.938  -1.739  0.00  0.00           C+0
HETATM   31  C   UNK     0     -10.492   1.324  -0.990  0.00  0.00           C+0
HETATM   32  O   UNK     0     -11.090   0.519  -0.245  0.00  0.00           O+0
HETATM   33  O   UNK     0     -11.031   2.609  -1.078  0.00  0.00           O+0
HETATM   34  C   UNK     0      -3.689   1.520   0.122  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.562   0.963  -0.587  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.370   1.105  -1.812  0.00  0.00           O+0
HETATM   37  H   UNK     0      10.393   1.375  -3.149  0.00  0.00           H+0
HETATM   38  H   UNK     0       9.318  -0.077  -3.355  0.00  0.00           H+0
HETATM   39  H   UNK     0       8.614   1.549  -3.132  0.00  0.00           H+0
HETATM   40  H   UNK     0      10.918   1.353   0.065  0.00  0.00           H+0
HETATM   41  H   UNK     0      11.609   0.486  -1.357  0.00  0.00           H+0
HETATM   42  H   UNK     0      10.752  -0.432  -0.075  0.00  0.00           H+0
HETATM   43  H   UNK     0       7.424   0.760  -1.224  0.00  0.00           H+0
HETATM   44  H   UNK     0       9.364   0.462   1.133  0.00  0.00           H+0
HETATM   45  H   UNK     0       7.837   1.320   1.287  0.00  0.00           H+0
HETATM   46  H   UNK     0       7.711  -0.883   2.354  0.00  0.00           H+0
HETATM   47  H   UNK     0       8.262  -1.704   0.820  0.00  0.00           H+0
HETATM   48  H   UNK     0       6.819  -1.458  -1.236  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.373  -0.408  -1.064  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.304  -2.188  -0.750  0.00  0.00           H+0
HETATM   51  H   UNK     0       5.532  -1.080   2.763  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.536  -2.329   1.748  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.747  -1.475   0.217  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.144  -0.236   2.943  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.558   0.723   1.498  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.408  -2.080   1.145  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.610  -2.203   2.411  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.179  -1.226   2.762  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.795   1.453   0.489  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.096   1.096  -0.940  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.589   1.970   0.490  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.836  -1.521   1.727  0.00  0.00           H+0
HETATM   63  H   UNK     0      -5.685   2.134   1.517  0.00  0.00           H+0
HETATM   64  H   UNK     0      -5.252   1.030   2.847  0.00  0.00           H+0
HETATM   65  H   UNK     0      -8.210  -1.681   0.212  0.00  0.00           H+0
HETATM   66  H   UNK     0      -9.239  -0.338   0.672  0.00  0.00           H+0
HETATM   67  H   UNK     0      -7.071  -1.627  -1.811  0.00  0.00           H+0
HETATM   68  H   UNK     0      -7.065  -0.071  -2.754  0.00  0.00           H+0
HETATM   69  H   UNK     0      -8.176  -1.340  -3.272  0.00  0.00           H+0
HETATM   70  H   UNK     0      -9.906  -1.424  -2.684  0.00  0.00           H+0
HETATM   71  H   UNK     0      -8.503   1.735  -1.698  0.00  0.00           H+0
HETATM   72  H   UNK     0      -9.589   0.937  -2.833  0.00  0.00           H+0
HETATM   73  H   UNK     0     -10.675   3.235  -1.818  0.00  0.00           H+0
HETATM   74  H   UNK     0      -4.017   2.528  -0.027  0.00  0.00           H+0
CONECT    1    2   37   38   39                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   40   41   42                                             
CONECT    4    2    5   43                                                  
CONECT    5    4    6   44   45                                             
CONECT    6    5    7   46   47                                             
CONECT    7    6    8    9                                                  
CONECT    8    7   48   49   50                                             
CONECT    9    7   10   51                                                  
CONECT   10    9   11   52   53                                             
CONECT   11   10   12   54   55                                             
CONECT   12   11   13   14                                                  
CONECT   13   12   56   57   58                                             
CONECT   14   12   15   59                                                  
CONECT   15   14   16   60   61                                             
CONECT   16   15   17   18   35                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   16   62                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   34                                                  
CONECT   22   21   23   63   64                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   65   66                                             
CONECT   27   26   28   29   30                                             
CONECT   28   27   67   68   69                                             
CONECT   29   27   70                                                       
CONECT   30   27   31   71   72                                             
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   73                                                       
CONECT   34   21   35   74                                                  
CONECT   35   34   36   16                                                  
CONECT   36   35                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    3                                                            
CONECT   41    3                                                            
CONECT   42    3                                                            
CONECT   43    4                                                            
CONECT   44    5                                                            
CONECT   45    5                                                            
CONECT   46    6                                                            
CONECT   47    6                                                            
CONECT   48    8                                                            
CONECT   49    8                                                            
CONECT   50    8                                                            
CONECT   51    9                                                            
CONECT   52   10                                                            
CONECT   53   10                                                            
CONECT   54   11                                                            
CONECT   55   11                                                            
CONECT   56   13                                                            
CONECT   57   13                                                            
CONECT   58   13                                                            
CONECT   59   14                                                            
CONECT   60   15                                                            
CONECT   61   15                                                            
CONECT   62   18                                                            
CONECT   63   22                                                            
CONECT   64   22                                                            
CONECT   65   26                                                            
CONECT   66   26                                                            
CONECT   67   28                                                            
CONECT   68   28                                                            
CONECT   69   28                                                            
CONECT   70   29                                                            
CONECT   71   30                                                            
CONECT   72   30                                                            
CONECT   73   33                                                            
CONECT   74   34                                                            
MASTER        0    0    0    0    0    0    0    0   74    0  150    0
END

RDKit          3D

74 75  0  0  0  0  0  0  0  0999 V2000
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    9.4751    0.6761   -1.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7597    0.5184   -0.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2466   -1.0629    0.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9051   -1.2341   -0.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2659   -1.1598    1.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0794   -0.1937    1.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.9184    1.3533    0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5356   -2.3290    1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7469   -1.4749    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1440   -0.2357    2.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577    0.7229    1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083   -2.0797    1.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6102   -2.2025    2.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -1.2262    2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951    1.4532    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955    1.0958   -0.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5885    1.9699    0.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356   -1.5206    1.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6848    2.1338    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2518    1.0298    2.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2099   -1.6805    0.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2385   -0.3375    0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0705   -1.6271   -1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0653   -0.0710   -2.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1757   -1.3399   -3.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9057   -1.4240   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5030    1.7349   -1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5893    0.9373   -2.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6752    3.2346   -1.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0174    2.5281   -0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
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 21 34  2  0
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 18 16  1  0
 35 16  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  8 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
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 34 74  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
5-{[(1S)-2,5-dioxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoate	Generator

Chemical Formula

C₂₈H₃₈O₈

Average Mass

502.6040 Da

Monoisotopic Mass

502.25667 Da

IUPAC Name

(3S)-5-{[(1S,6R)-2,5-dioxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

Traditional Name

(3S)-5-{[(1S,6R)-2,5-dioxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC12O[C@@H]1C(=O)C(COC(=O)CC(C)(O)CC(O)=O)=CC2=O

InChI Identifier

InChI=1S/C28H38O8/c1-18(2)8-6-9-19(3)10-7-11-20(4)12-13-28-22(29)14-21(25(33)26(28)36-28)17-35-24(32)16-27(5,34)15-23(30)31/h8,10,12,14,26,34H,6-7,9,11,13,15-17H2,1-5H3,(H,30,31)/b19-10+,20-12+/t26-,27?,28?/m1/s1

InChI Key

NIBXHVDVUJEQPO-OFWAVEGMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus niger	NPAtlas	11031048

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Cyclohexenone
Methyl-branched fatty acid
Short-chain hydroxy acid
Hydroxy fatty acid
Heterocyclic fatty acid
Fatty acid ester
Branched fatty acid
Fatty acyl
Dicarboxylic acid or derivatives
Tertiary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.54	ALOGPS
logP	4.47	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	130.5 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	137.35 m³·mol⁻¹	ChemAxon
Polarizability	55.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA013738

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78440342

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586902

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bugni TS, Abbanat D, Bernan VS, Maiese WM, Greenstein M, Van Wagoner RM, Ireland CM: Yanuthones: novel metabolites from a marine isolate of Aspergillus niger. J Org Chem. 2000 Oct 20;65(21):7195-200. doi: 10.1021/jo0006831. [PubMed:11031048 ]

Showing NP-Card for Yanuthone D (NP0003480)

MOL for NP0003480 (Yanuthone D)

3D MOL for NP0003480 (Yanuthone D)

3D SDF for NP0003480 (Yanuthone D)

3D-SDF for NP0003480 (Yanuthone D)

PDB for NP0003480 (Yanuthone D)

3D PDB for NP0003480 (Yanuthone D)

SMILES for NP0003480 (Yanuthone D)

INCHI for NP0003480 (Yanuthone D)

Structure for NP0003480 (Yanuthone D)

3D Structure for NP0003480 (Yanuthone D)