NP-MRD: Showing NP-Card for Purpurogenolide B (NP0015373)

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Record Information

Version

1.0

Created at

2021-01-06 00:34:13 UTC

Updated at

2021-07-15 17:19:46 UTC

NP-MRD ID

NP0015373

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Purpurogenolide B

Provided By

NPAtlas

Description

Purpurogenolide B is found in Penicillium and Talaromyces purpureogenus. It was first documented in 2016 (PMID: 27120704). Based on a literature review very few articles have been published on methyl (1'R,2R,2'S,11'R,12'R,14'R,16'S)-11',16'-dihydroxy-2',6',6',11',14',16'-hexamethyl-8',15',17'-trioxo-7'-oxaspiro[oxirane-2,18'-tetracyclo[12.3.1.0²,¹².0⁵,¹⁰]Octadecane]-4',9'-diene-1'-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117183D          

 67 71  0  0  0  0            999 V2000
   -0.6765    5.0293   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236    3.6554   -0.0534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489    2.7438    0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4768    3.2940    0.6911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096    1.2954    0.6271 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2148    1.2034    1.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013    1.7830    0.8644 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4488    0.4330    2.5674 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9204    0.1033    2.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0621    1.2918    3.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3974   -0.7673    2.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292   -1.8119    2.9727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7475   -0.6613    1.9655 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7823   -1.1574    2.9733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7873   -1.4979    0.7056 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7858   -0.9417   -0.2424 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0447    0.4797   -0.6419 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4525    0.5801   -1.3085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1182    1.0552   -1.6322 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2867    0.6399   -1.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7600   -0.6163   -1.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526   -1.8283   -1.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5154   -2.9823   -1.9798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542   -3.0696   -2.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4716   -4.1785   -2.5702 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6541   -1.8907   -2.2677 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2207   -0.6930   -1.6971 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8862   -0.5743   -0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8057    0.4160   -2.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5057   -1.8789   -1.3999 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0208   -3.2755   -1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2194   -1.3859   -2.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1438    0.7233    1.5855 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5302    1.0695    1.6391 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6068    1.6215    2.5356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8704    5.2871   -1.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296    5.2873    0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1989    5.5764    0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1738   -0.7577    2.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1049   -0.1668    3.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5576    0.9683    2.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8479    1.9130    3.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3424   -1.9880    3.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0598   -0.3753    3.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6343   -1.5891    2.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4827   -2.5358    1.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8232   -1.5351    0.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1759   -0.8888    0.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763    1.5420   -1.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3297    0.6534   -2.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0585   -0.2936   -1.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1678    2.1778   -1.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5783    0.8236   -2.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0486    1.3983   -1.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8866   -3.8555   -1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9932   -1.5496    0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4852    0.2387    0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9545   -0.2625   -0.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0642    1.2478   -1.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0709    0.7554   -3.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7342    0.0666   -3.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1224   -3.7734   -2.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0879   -3.1486   -0.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045   -3.8440   -0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6960   -1.6423   -3.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2144    0.3497    2.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1240    1.7138    0.9968 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
  3  4  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
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 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  6  0  0  0
 13 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 17  5  1  0  0  0  0
 27 21  1  0  0  0  0
 33 35  1  1  0  0  0
 33  5  1  0  0  0  0
 30 16  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  9 39  1  0  0  0  0
  9 40  1  0  0  0  0
  9 41  1  0  0  0  0
 10 42  1  0  0  0  0
 14 43  1  0  0  0  0
 14 44  1  0  0  0  0
 14 45  1  0  0  0  0
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 15 47  1  0  0  0  0
 16 48  1  1  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
 18 51  1  0  0  0  0
 19 52  1  0  0  0  0
 19 53  1  0  0  0  0
 20 54  1  0  0  0  0
 23 55  1  0  0  0  0
 28 56  1  0  0  0  0
 28 57  1  0  0  0  0
 28 58  1  0  0  0  0
 29 59  1  0  0  0  0
 29 60  1  0  0  0  0
 29 61  1  0  0  0  0
 31 62  1  0  0  0  0
 31 63  1  0  0  0  0
 31 64  1  0  0  0  0
 32 65  1  0  0  0  0
 34 66  1  0  0  0  0
 34 67  1  0  0  0  0
M  END

     RDKit          3D

 67 71  0  0  0  0  0  0  0  0999 V2000
   -0.6765    5.0293   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236    3.6554   -0.0534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489    2.7438    0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4768    3.2940    0.6911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096    1.2954    0.6271 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2148    1.2034    1.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013    1.7830    0.8644 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4488    0.4330    2.5674 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9204    0.1033    2.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0621    1.2918    3.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3974   -0.7673    2.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292   -1.8119    2.9727 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7823   -1.1574    2.9733 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0447    0.4797   -0.6419 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.7600   -0.6163   -1.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526   -1.8283   -1.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9542   -3.0696   -2.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4716   -4.1785   -2.5702 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8862   -0.5743   -0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8057    0.4160   -2.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5057   -1.8789   -1.3999 C   0  0  1  0  0  0  0  0  0  0  0  0
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 34 67  1  0
M  END


  Mrv1652306242117183D          

 67 71  0  0  0  0            999 V2000
   -0.6765    5.0293   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236    3.6554   -0.0534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489    2.7438    0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4768    3.2940    0.6911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096    1.2954    0.6271 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2148    1.2034    1.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013    1.7830    0.8644 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4488    0.4330    2.5674 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9204    0.1033    2.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0621    1.2918    3.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3974   -0.7673    2.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292   -1.8119    2.9727 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7600   -0.6163   -1.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9542   -3.0696   -2.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3297    0.6534   -2.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5783    0.8236   -2.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0486    1.3983   -1.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8866   -3.8555   -1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9932   -1.5496    0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9545   -0.2625   -0.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0642    1.2478   -1.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0709    0.7554   -3.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7342    0.0666   -3.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1224   -3.7734   -2.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0879   -3.1486   -0.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045   -3.8440   -0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6960   -1.6423   -3.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2144    0.3497    2.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1240    1.7138    0.9968 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
  3  4  2  0  0  0  0
  5  3  1  6  0  0  0
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  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
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  8 11  1  0  0  0  0
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 17  5  1  0  0  0  0
 27 21  1  0  0  0  0
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 33  5  1  0  0  0  0
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  1 37  1  0  0  0  0
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 34 66  1  0  0  0  0
 34 67  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0015373

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1(C(=O)[C@]2(C([H])([H])[H])C([H])([H])[C@]3([H])[C@](C([H])([H])[H])(C([H])([H])C([H])=C4C(=C([H])C(=O)OC4(C([H])([H])[H])C([H])([H])[H])[C@@]3(O[H])C([H])([H])[H])[C@](C(=O)OC([H])([H])[H])(C1=O)[C@]21OC1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O9/c1-20(2)13-8-9-21(3)15(23(5,31)14(13)10-16(27)35-20)11-22(4)17(28)24(6,32)18(29)26(21,19(30)33-7)25(22)12-34-25/h8,10,15,31-32H,9,11-12H2,1-7H3/t15-,21+,22+,23+,24+,25-,26-/m1/s1

> <INCHI_KEY>
XGYXSVBDXZSQAO-RGOIRPBRSA-N

> <FORMULA>
C26H32O9

> <MOLECULAR_WEIGHT>
488.533

> <EXACT_MASS>
488.20463261

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
49.02338142198997

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1'R,2R,2'S,11'R,12'R,14'R,16'S)-11',16'-dihydroxy-2',6',6',11',14',16'-hexamethyl-8',15',17'-trioxo-7'-oxaspiro[oxirane-2,18'-tetracyclo[12.3.1.0^{2,12}.0^{5,10}]octadecane]-4',9'-diene-1'-carboxylate

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
1.8083365806666676

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.06657099658257

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.492254080885456

> <JCHEM_PKA_STRONGEST_BASIC>
-3.207592900168076

> <JCHEM_POLAR_SURFACE_AREA>
139.73

> <JCHEM_REFRACTIVITY>
122.49109999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1'R,2R,2'S,11'R,12'R,14'R,16'S)-11',16'-dihydroxy-2',6',6',11',14',16'-hexamethyl-8',15',17'-trioxo-7'-oxaspiro[oxirane-2,18'-tetracyclo[12.3.1.0^{2,12}.0^{5,10}]octadecane]-4',9'-diene-1'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 67 71  0  0  0  0  0  0  0  0999 V2000
   -0.6765    5.0293   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236    3.6554   -0.0534 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2148    1.2034    1.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013    1.7830    0.8644 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4488    0.4330    2.5674 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.0621    1.2918    3.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
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  6  7  2  0
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  1 37  1  0
  1 38  1  0
  9 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 14 43  1  0
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 15 47  1  0
 16 48  1  1
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 29 59  1  0
 29 60  1  0
 29 61  1  0
 31 62  1  0
 31 63  1  0
 31 64  1  0
 32 65  1  0
 34 66  1  0
 34 67  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      -0.677   5.029  -0.235  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.424   3.655  -0.053  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.349   2.744   0.426  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.477   3.294   0.691  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.110   1.295   0.627  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.215   1.203   1.317  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.201   1.783   0.864  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.449   0.433   2.567  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.920   0.103   2.669  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.062   1.292   3.616  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.397  -0.767   2.535  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.029  -1.812   2.973  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.748  -0.661   1.966  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.782  -1.157   2.973  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.787  -1.498   0.706  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.786  -0.942  -0.242  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.045   0.480  -0.642  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.453   0.580  -1.309  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.118   1.055  -1.632  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.287   0.640  -1.649  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.760  -0.616  -1.673  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.953  -1.828  -1.688  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.515  -2.982  -1.980  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.954  -3.070  -2.296  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.472  -4.178  -2.570  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.654  -1.891  -2.268  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.221  -0.693  -1.697  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.886  -0.574  -0.349  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.806   0.416  -2.572  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.506  -1.879  -1.400  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.021  -3.276  -1.171  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.219  -1.386  -2.502  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.144   0.723   1.585  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.530   1.069   1.639  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.607   1.621   2.536  0.00  0.00           O+0
HETATM   36  H   UNK     0      -0.870   5.287  -1.284  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.530   5.287   0.425  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.199   5.576   0.186  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.174  -0.758   2.016  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.105  -0.167   3.748  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.558   0.968   2.450  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.848   1.913   3.721  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.342  -1.988   3.590  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.060  -0.375   3.701  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.634  -1.589   2.418  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.483  -2.536   1.004  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.823  -1.535   0.380  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.176  -0.889   0.359  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.876   1.542  -1.014  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.330   0.653  -2.430  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.059  -0.294  -1.140  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.168   2.178  -1.653  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.578   0.824  -2.670  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.049   1.398  -1.654  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.887  -3.856  -1.978  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.993  -1.550   0.161  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.485   0.239   0.264  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.955  -0.263  -0.559  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.064   1.248  -1.899  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.071   0.755  -3.319  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.734   0.067  -3.064  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.122  -3.773  -2.158  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.088  -3.149  -0.820  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.504  -3.844  -0.404  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.696  -1.642  -3.323  0.00  0.00           H+0
HETATM   66  H   UNK     0      -4.214   0.350   2.188  0.00  0.00           H+0
HETATM   67  H   UNK     0      -4.124   1.714   0.997  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   17   33                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8   39   40   41                                             
CONECT   10    8   42                                                       
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   33                                             
CONECT   14   13   43   44   45                                             
CONECT   15   13   16   46   47                                             
CONECT   16   15   17   30   48                                             
CONECT   17   16   18   19    5                                             
CONECT   18   17   49   50   51                                             
CONECT   19   17   20   52   53                                             
CONECT   20   19   21   54                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23   30                                                  
CONECT   23   22   24   55                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29   21                                             
CONECT   28   27   56   57   58                                             
CONECT   29   27   59   60   61                                             
CONECT   30   22   31   32   16                                             
CONECT   31   30   62   63   64                                             
CONECT   32   30   65                                                       
CONECT   33   13   34   35    5                                             
CONECT   34   33   35   66   67                                             
CONECT   35   34   33                                                       
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    9                                                            
CONECT   40    9                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   19                                                            
CONECT   54   20                                                            
CONECT   55   23                                                            
CONECT   56   28                                                            
CONECT   57   28                                                            
CONECT   58   28                                                            
CONECT   59   29                                                            
CONECT   60   29                                                            
CONECT   61   29                                                            
CONECT   62   31                                                            
CONECT   63   31                                                            
CONECT   64   31                                                            
CONECT   65   32                                                            
CONECT   66   34                                                            
CONECT   67   34                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  142    0
END

RDKit          3D

67 71  0  0  0  0  0  0  0  0999 V2000
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  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  6
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  1
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  1
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 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  1
 27 29  1  0
 22 30  1  0
 30 31  1  0
 30 32  1  6
 13 33  1  0
 33 34  1  0
 34 35  1  0
 17  5  1  0
 27 21  1  0
 33 35  1  1
 33  5  1  0
 30 16  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  9 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  1
 18 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 23 55  1  0
 28 56  1  0
 28 57  1  0
 28 58  1  0
 29 59  1  0
 29 60  1  0
 29 61  1  0
 31 62  1  0
 31 63  1  0
 31 64  1  0
 32 65  1  0
 34 66  1  0
 34 67  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl (1'r,2R,2's,11'r,12'r,14'r,16's)-11',16'-dihydroxy-2',6',6',11',14',16'-hexamethyl-8',15',17'-trioxo-7'-oxaspiro[oxirane-2,18'-tetracyclo[12.3.1.0,.0,]octadecane]-4',9'-diene-1'-carboxylic acid	Generator

Chemical Formula

C₂₆H₃₂O₉

Average Mass

488.5330 Da

Monoisotopic Mass

488.20463 Da

IUPAC Name

methyl (1'R,2R,2'S,11'R,12'R,14'R,16'S)-11',16'-dihydroxy-2',6',6',11',14',16'-hexamethyl-8',15',17'-trioxo-7'-oxaspiro[oxirane-2,18'-tetracyclo[12.3.1.0^{2,12}.0^{5,10}]octadecane]-4',9'-diene-1'-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]12C(=O)[C@@](C)(O)C(=O)[C@](C)(C[C@@H]3[C@]1(C)CC=C1C(=CC(=O)OC1(C)C)[C@]3(C)O)[C@]21CO1

InChI Identifier

InChI=1S/C26H32O9/c1-20(2)13-8-9-21(3)15(23(5,31)14(13)10-16(27)35-20)11-22(4)17(28)24(6,32)18(29)26(21,19(30)33-7)25(22)12-34-25/h8,10,15,31-32H,9,11-12H2,1-7H3/t15-,21+,22+,23+,24+,25-,26-/m1/s1

InChI Key

XGYXSVBDXZSQAO-RGOIRPBRSA-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
Penicillium	NPAtlas	27120704
Penicillium purpurogenum	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	2.1	ALOGPS
logP	1.81	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.49	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	139.73 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	122.49 m³·mol⁻¹	ChemAxon
Polarizability	49.02 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA021946

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

76785990

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132566493

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sun J, Zhu ZX, Song YL, Dong D, Zheng J, Liu T, Zhao YF, Ferreira D, Zjawiony JK, Tu PF, Li J: Nitric Oxide Inhibitory Meroterpenoids from the Fungus Penicillium purpurogenum MHZ 111. J Nat Prod. 2016 May 27;79(5):1415-22. doi: 10.1021/acs.jnatprod.6b00160. Epub 2016 Apr 27. [PubMed:27120704 ]

Showing NP-Card for Purpurogenolide B (NP0015373)

MOL for NP0015373 (Purpurogenolide B)

3D MOL for NP0015373 (Purpurogenolide B)

3D SDF for NP0015373 (Purpurogenolide B)

3D-SDF for NP0015373 (Purpurogenolide B)

PDB for NP0015373 (Purpurogenolide B)

3D PDB for NP0015373 (Purpurogenolide B)

SMILES for NP0015373 (Purpurogenolide B)

INCHI for NP0015373 (Purpurogenolide B)

Structure for NP0015373 (Purpurogenolide B)

3D Structure for NP0015373 (Purpurogenolide B)