NP-MRD: Showing NP-Card for Purpurogemutantin (NP0010981)

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Record Information

Version

1.0

Created at

2021-01-05 20:45:50 UTC

Updated at

2021-07-15 17:07:38 UTC

NP-MRD ID

NP0010981

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Purpurogemutantin

Provided By

NPAtlas

Description

Purpurogemutantin is found in Penicillium and Talaromyces purpureogenus. It was first documented in 2012 (PMID: 22822371). Based on a literature review very few articles have been published on (1S,5R,9R)-1-{[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]methyl}-5,9-dihydroxy-6-(hydroxymethyl)-2-oxabicyclo[3.3.1]Non-6-ene-3,8-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107433D          

 64 67  0  0  0  0            999 V2000
   -0.2286   -3.0792    1.7849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8944   -2.4319    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2195   -2.9670    0.4625 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.7104    0.5263    1.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
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  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 29 63  1  6  0  0  0
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M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242107433D          

 64 67  0  0  0  0            999 V2000
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    0.9175   -0.9039    0.7870 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8504    0.1755    0.4550 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4918    1.4925    0.6128 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8970    2.4962   -0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1274    3.4705   -0.5462 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2669    2.4126   -0.8143 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6625    0.9823   -1.0398 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1916    0.9287   -2.3497 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7245    0.6657   -0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344    0.7449   -0.4455 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9959    0.4153    0.5917 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9886   -0.0021    1.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6830   -0.4245    2.6293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447   -0.0071   -0.8808 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1271   -1.2755   -0.9349 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5249   -3.8221    1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6465   -0.2340    1.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4601    1.5440    1.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4315   -1.2348   -1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7087   -1.0182   -0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4445    0.2246   -1.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159    2.3969   -0.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3215    1.7256   -1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9927    2.4389   -1.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2827    0.7379   -2.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2734    0.8104   -1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0315    1.9485    0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4505    0.5547    2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8221    1.1682    1.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856   -0.5352    2.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3814   -1.4167   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5598   -1.8681    0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8290   -0.8663    1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    2.9320   -0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3654    3.0484   -1.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    1.7748   -2.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3554    0.0888   -1.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    1.7802   -0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1117   -0.5412    0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1002    0.2438    1.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8262    0.0651   -1.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132   -1.5794   -0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  6  9  1  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  1  0  0  0
 12 14  1  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  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
 14  2  1  0  0  0  0
 27 16  1  0  0  0  0
 12  5  1  0  0  0  0
 29 16  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  4 35  1  0  0  0  0
  4 36  1  0  0  0  0
  5 37  1  6  0  0  0
  7 38  1  0  0  0  0
  7 39  1  0  0  0  0
  7 40  1  0  0  0  0
  8 41  1  0  0  0  0
  8 42  1  0  0  0  0
  8 43  1  0  0  0  0
  9 44  1  0  0  0  0
  9 45  1  0  0  0  0
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 11 48  1  0  0  0  0
 11 49  1  0  0  0  0
 13 50  1  0  0  0  0
 13 51  1  0  0  0  0
 13 52  1  0  0  0  0
 14 53  1  6  0  0  0
 15 54  1  0  0  0  0
 15 55  1  0  0  0  0
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 20 57  1  0  0  0  0
 22 58  1  0  0  0  0
 24 59  1  0  0  0  0
 24 60  1  0  0  0  0
 25 61  1  0  0  0  0
 26 62  1  0  0  0  0
 29 63  1  6  0  0  0
 30 64  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010981

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C([H])C(=O)[C@]2(OC(=O)C([H])([H])[C@]1(O[H])[C@@]2([H])O[H])C([H])([H])[C@@]1([H])C(=C([H])[H])C([H])([H])C([H])([H])[C@@]2([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]12C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O6/c1-14-6-7-17-21(2,3)8-5-9-22(17,4)16(14)11-24-18(26)10-15(13-25)23(29,20(24)28)12-19(27)30-24/h10,16-17,20,25,28-29H,1,5-9,11-13H2,2-4H3/t16-,17-,20+,22+,23+,24+/m0/s1

> <INCHI_KEY>
KEWKLOYQCZOZIL-UNFUUYLFSA-N

> <FORMULA>
C24H34O6

> <MOLECULAR_WEIGHT>
418.53

> <EXACT_MASS>
418.235538815

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
45.433421927485576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,9R)-1-{[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]methyl}-5,9-dihydroxy-6-(hydroxymethyl)-2-oxabicyclo[3.3.1]non-6-ene-3,8-dione

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
2.2696704539999994

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.784046251734456

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.397931761414934

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7883050223344226

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
111.34959999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,9R)-1-{[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]methyl}-5,9-dihydroxy-6-(hydroxymethyl)-2-oxabicyclo[3.3.1]non-6-ene-3,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
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   -4.7104    0.5263    1.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5855    1.5278   -0.9077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2239    1.4419   -1.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1559    1.0522   -0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4706   -0.0911    0.3372 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4736    0.2888    1.8050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959   -1.1484    0.1928 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.1916    0.9287   -2.3497 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7245    0.6657   -0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344    0.7449   -0.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9886   -0.0021    1.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6830   -0.4245    2.6293 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9585   -1.5754    1.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8214    0.6101    0.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6465   -0.2340    1.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3814   -1.4167   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5598   -1.8681    0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8290   -0.8663    1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    2.9320   -0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3654    3.0484   -1.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    1.7748   -2.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3554    0.0888   -1.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    1.7802   -0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1117   -0.5412    0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1002    0.2438    1.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8262    0.0651   -1.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132   -1.5794   -0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 26 27  1  0
 27 28  2  0
 21 29  1  0
 29 30  1  0
 14  2  1  0
 27 16  1  0
 12  5  1  0
 29 16  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  6
  7 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
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  9 45  1  0
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 11 48  1  0
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 20 56  1  0
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 22 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 26 62  1  0
 29 63  1  6
 30 64  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      -0.229  -3.079   1.785  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.894  -2.432   0.871  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.220  -2.967   0.463  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.192  -1.831   0.845  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.785  -0.695  -0.082  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.938   0.227  -0.243  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.710   0.526   1.016  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.951  -0.488  -1.166  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.586   1.528  -0.908  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.224   1.442  -1.556  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.156   1.052  -0.559  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.471  -0.091   0.337  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.474   0.289   1.805  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.396  -1.148   0.193  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.918  -0.904   0.787  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.850   0.176   0.455  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.492   1.492   0.613  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.897   2.496  -0.245  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.127   3.470  -0.546  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.267   2.413  -0.814  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.663   0.982  -1.040  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.192   0.929  -2.350  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.724   0.666  -0.064  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.134   0.745  -0.446  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.996   0.415   0.592  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.364   0.314   1.147  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.989  -0.002   1.492  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.683  -0.425   2.629  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.545  -0.007  -0.881  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.127  -1.276  -0.935  0.00  0.00           O+0
HETATM   31  H   UNK     0       0.735  -2.822   2.184  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.655  -3.997   2.230  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.320  -3.106  -0.625  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.525  -3.822   1.060  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.229  -2.110   0.649  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.958  -1.575   1.883  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.564  -1.186  -1.080  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.821   0.610   0.792  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.646  -0.234   1.794  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.460   1.544   1.437  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.431  -1.235  -1.800  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.709  -1.018  -0.591  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.444   0.225  -1.837  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.616   2.397  -0.219  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.322   1.726  -1.705  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.993   2.439  -1.972  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.283   0.738  -2.406  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.273   0.810  -1.167  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.032   1.948   0.115  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.450   0.555   2.208  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.822   1.168   1.962  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.086  -0.535   2.459  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.381  -1.417  -0.889  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.560  -1.868   0.700  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.829  -0.866   1.942  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.930   2.932  -0.060  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.365   3.048  -1.729  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.651   1.775  -2.588  0.00  0.00           H+0
HETATM   59  H   UNK     0       6.355   0.089  -1.315  0.00  0.00           H+0
HETATM   60  H   UNK     0       6.403   1.780  -0.780  0.00  0.00           H+0
HETATM   61  H   UNK     0       7.112  -0.541   0.735  0.00  0.00           H+0
HETATM   62  H   UNK     0       5.100   0.244   1.960  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.826   0.065  -1.711  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.413  -1.579  -0.051  0.00  0.00           H+0
CONECT    1    2   31   32                                                  
CONECT    2    1    3   14                                                  
CONECT    3    2    4   33   34                                             
CONECT    4    3    5   35   36                                             
CONECT    5    4    6   12   37                                             
CONECT    6    5    7    8    9                                             
CONECT    7    6   38   39   40                                             
CONECT    8    6   41   42   43                                             
CONECT    9    6   10   44   45                                             
CONECT   10    9   11   46   47                                             
CONECT   11   10   12   48   49                                             
CONECT   12   11   13   14    5                                             
CONECT   13   12   50   51   52                                             
CONECT   14   12   15    2   53                                             
CONECT   15   14   16   54   55                                             
CONECT   16   15   17   27   29                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   56   57                                             
CONECT   21   20   22   23   29                                             
CONECT   22   21   58                                                       
CONECT   23   21   24   26                                                  
CONECT   24   23   25   59   60                                             
CONECT   25   24   61                                                       
CONECT   26   23   27   62                                                  
CONECT   27   26   28   16                                                  
CONECT   28   27                                                            
CONECT   29   21   30   16   63                                             
CONECT   30   29   64                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    7                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    9                                                            
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   10                                                            
CONECT   48   11                                                            
CONECT   49   11                                                            
CONECT   50   13                                                            
CONECT   51   13                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   15                                                            
CONECT   55   15                                                            
CONECT   56   20                                                            
CONECT   57   20                                                            
CONECT   58   22                                                            
CONECT   59   24                                                            
CONECT   60   24                                                            
CONECT   61   25                                                            
CONECT   62   26                                                            
CONECT   63   29                                                            
CONECT   64   30                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  134    0
END

RDKit          3D

64 67  0  0  0  0  0  0  0  0999 V2000
   -0.2286   -3.0792    1.7849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8944   -2.4319    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2195   -2.9670    0.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1919   -1.8307    0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7853   -0.6950   -0.0824 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9377    0.2270   -0.2430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7104    0.5263    1.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9508   -0.4877   -1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5855    1.5278   -0.9077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2239    1.4419   -1.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1559    1.0522   -0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4706   -0.0911    0.3372 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4736    0.2888    1.8050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959   -1.1484    0.1928 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9175   -0.9039    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8504    0.1755    0.4550 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4918    1.4925    0.6128 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8970    2.4962   -0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1274    3.4705   -0.5462 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2669    2.4126   -0.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625    0.9823   -1.0398 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1916    0.9287   -2.3497 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7245    0.6657   -0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344    0.7449   -0.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9959    0.4153    0.5917 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3644    0.3141    1.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886   -0.0021    1.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6830   -0.4245    2.6293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447   -0.0071   -0.8808 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1271   -1.2755   -0.9349 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7345   -2.8224    2.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6551   -3.9967    2.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3202   -3.1056   -0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5249   -3.8221    1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2292   -2.1096    0.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9585   -1.5754    1.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5637   -1.1857   -1.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8214    0.6101    0.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6465   -0.2340    1.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4601    1.5440    1.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4315   -1.2348   -1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7087   -1.0182   -0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4445    0.2246   -1.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159    2.3969   -0.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3215    1.7256   -1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9927    2.4389   -1.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2827    0.7379   -2.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2734    0.8104   -1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0315    1.9485    0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4505    0.5547    2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8221    1.1682    1.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856   -0.5352    2.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3814   -1.4167   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5598   -1.8681    0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8290   -0.8663    1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    2.9320   -0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3654    3.0484   -1.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    1.7748   -2.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3554    0.0888   -1.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    1.7802   -0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1117   -0.5412    0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1002    0.2438    1.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8262    0.0651   -1.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132   -1.5794   -0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 26 27  1  0
 27 28  2  0
 21 29  1  0
 29 30  1  0
 14  2  1  0
 27 16  1  0
 12  5  1  0
 29 16  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  6
  7 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 13 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  6
 15 54  1  0
 15 55  1  0
 20 56  1  0
 20 57  1  0
 22 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 26 62  1  0
 29 63  1  6
 30 64  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₄H₃₄O₆

Average Mass

418.5300 Da

Monoisotopic Mass

418.23554 Da

IUPAC Name

(1S,5R,9R)-1-{[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]methyl}-5,9-dihydroxy-6-(hydroxymethyl)-2-oxabicyclo[3.3.1]non-6-ene-3,8-dione

Traditional Name

(1S,5R,9R)-1-{[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]methyl}-5,9-dihydroxy-6-(hydroxymethyl)-2-oxabicyclo[3.3.1]non-6-ene-3,8-dione

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@]2(C)[C@@H](C[C@]34OC(=O)C[C@](O)([C@H]3O)C(CO)=CC4=O)C(=C)CC[C@@H]12

InChI Identifier

InChI=1S/C24H34O6/c1-14-6-7-17-21(2,3)8-5-9-22(17,4)16(14)11-24-18(26)10-15(13-25)23(29,20(24)28)12-19(27)30-24/h10,16-17,20,25,28-29H,1,5-9,11-13H2,2-4H3/t16-,17-,20+,22+,23+,24+/m0/s1

InChI Key

KEWKLOYQCZOZIL-UNFUUYLFSA-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	22822371
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	2.28	ALOGPS
logP	2.27	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.4	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	111.35 m³·mol⁻¹	ChemAxon
Polarizability	45.43 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA028643

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29214833

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146684693

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fang SM, Cui CB, Li CW, Wu CJ, Zhang ZJ, Li L, Huang XJ, Ye WC: Purpurogemutantin and purpurogemutantidin, new drimenyl cyclohexenone derivatives produced by a mutant obtained by diethyl sulfate mutagenesis of a marine-derived Penicillium purpurogenum G59. Mar Drugs. 2012 Jun;10(6):1266-87. doi: 10.3390/md10061266. Epub 2012 Jun 4. [PubMed:22822371 ]

Showing NP-Card for Purpurogemutantin (NP0010981)

MOL for NP0010981 (Purpurogemutantin)

3D MOL for NP0010981 (Purpurogemutantin)

3D SDF for NP0010981 (Purpurogemutantin)

3D-SDF for NP0010981 (Purpurogemutantin)

PDB for NP0010981 (Purpurogemutantin)

3D PDB for NP0010981 (Purpurogemutantin)

SMILES for NP0010981 (Purpurogemutantin)

INCHI for NP0010981 (Purpurogemutantin)

Structure for NP0010981 (Purpurogemutantin)

3D Structure for NP0010981 (Purpurogemutantin)