NP-MRD: Showing NP-Card for Dictyopanine A (NP0003519)

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Record Information

Version

1.0

Created at

2020-12-09 00:44:38 UTC

Updated at

2021-07-15 16:46:37 UTC

NP-MRD ID

NP0003519

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dictyopanine A

Provided By

NPAtlas

Description

(1R,4S,7R,7aR)-7-(hydroxymethyl)-7a-methyl-1-(2-methylidene-3-oxopropyl)-2-oxo-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl (2E,4E)-4-methylnona-2,4-dienoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Dictyopanine A is found in Dictyopanus and Dictyopanus sp. HKI 0181. It was first documented in 2000 (PMID: 11079807). Based on a literature review very few articles have been published on (1R,4S,7R,7aR)-7-(hydroxymethyl)-7a-methyl-1-(2-methylidene-3-oxopropyl)-2-oxo-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl (2E,4E)-4-methylnona-2,4-dienoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117483D          

 64 65  0  0  0  0            999 V2000
   -3.3620    1.3053    2.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354    1.5284    1.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5951    0.9687    1.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9250    0.3181    2.5862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8970    2.3069    0.2110 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1461    1.6811   -1.1244 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7583    2.7582   -2.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224    3.7803   -2.4241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4590    2.3653   -2.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1940    1.1365   -2.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0656    0.2345   -2.5280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3339   -0.0548   -1.3523 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9993    0.1558   -1.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6481    0.6527   -2.1394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6178   -0.1896    0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9031   -0.0090    0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.3233    1.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9046   -0.9099    2.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8931   -0.0770    1.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7216   -0.3490    2.8114 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8254   -1.3440    2.4968 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7229   -0.8099    1.4181 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3667    0.5005    1.8564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5299   -1.0742   -3.0998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9391   -1.4338   -2.9403 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9390   -0.4658   -2.4446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0648   -1.2751   -1.8437 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1050   -0.5702   -1.3269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342    0.5386   -1.4849 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7835   -0.2360   -0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6726    0.7424    3.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3487    1.6691    2.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3229    1.1362    0.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4874    3.2759    0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8305    2.6951    0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2569    1.5290   -1.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8048    3.0413   -3.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3052    0.6541   -3.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125   -0.6057    0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4502    0.4262   -0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207   -1.6669    3.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740   -0.1456    3.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0301   -1.5140    2.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827    0.3495    0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2546    0.6182    3.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1588   -0.5986    3.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3757   -2.2918    2.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4466   -1.5543    3.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1489   -0.6223    0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5175   -1.5414    1.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4562    0.4650    2.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7203    1.3395    1.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3856    0.5781    1.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3186   -1.0326   -4.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8076   -1.8705   -2.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9642   -2.3569   -2.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3690   -1.8670   -3.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3758    0.0937   -3.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6589   -2.0486   -1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5356   -1.1432   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3420   -1.2172   -0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718   -0.6027    0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0091    0.2725    0.2324 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  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  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
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 24  1  0  0  0  0
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 26 27  1  0  0  0  0
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 26 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29  6  1  0  0  0  0
 29 10  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
  5 34  1  0  0  0  0
  5 35  1  0  0  0  0
  6 36  1  1  0  0  0
  9 37  1  0  0  0  0
 11 38  1  6  0  0  0
 15 39  1  0  0  0  0
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 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
 22 49  1  0  0  0  0
 22 50  1  0  0  0  0
 23 51  1  0  0  0  0
 23 52  1  0  0  0  0
 23 53  1  0  0  0  0
 24 54  1  0  0  0  0
 24 55  1  0  0  0  0
 25 56  1  0  0  0  0
 25 57  1  0  0  0  0
 26 58  1  6  0  0  0
 27 59  1  0  0  0  0
 27 60  1  0  0  0  0
 28 61  1  0  0  0  0
 30 62  1  0  0  0  0
 30 63  1  0  0  0  0
 30 64  1  0  0  0  0
M  END

     RDKit          3D

 64 65  0  0  0  0  0  0  0  0999 V2000
   -3.3620    1.3053    2.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354    1.5284    1.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5951    0.9687    1.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9250    0.3181    2.5862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8970    2.3069    0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1461    1.6811   -1.1244 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7583    2.7582   -2.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224    3.7803   -2.4241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4590    2.3653   -2.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1940    1.1365   -2.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0656    0.2345   -2.5280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3339   -0.0548   -1.3523 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9993    0.1558   -1.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6481    0.6527   -2.1394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6178   -0.1896    0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9031   -0.0090    0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.3233    1.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3342    0.5386   -1.4849 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7835   -0.2360   -0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3052    0.6541   -3.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8076   -1.8705   -2.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9642   -2.3569   -2.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6589   -2.0486   -1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0091    0.2725    0.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
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 30 64  1  0
M  END


  Mrv1652306242117483D          

 64 65  0  0  0  0            999 V2000
   -3.3620    1.3053    2.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354    1.5284    1.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5951    0.9687    1.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9250    0.3181    2.5862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8970    2.3069    0.2110 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1461    1.6811   -1.1244 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7583    2.7582   -2.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224    3.7803   -2.4241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4590    2.3653   -2.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1940    1.1365   -2.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0656    0.2345   -2.5280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3339   -0.0548   -1.3523 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6481    0.6527   -2.1394 O   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
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  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
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  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
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 11 24  1  0  0  0  0
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 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
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 29 30  1  1  0  0  0
 29  6  1  0  0  0  0
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  1 31  1  0  0  0  0
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  3 33  1  0  0  0  0
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 30 64  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003519

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@]1([H])C([H])([H])C([H])([H])[C@]([H])(OC(=O)C(\[H])=C(/[H])\C(=C(/[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])\C([H])([H])[H])C2=C([H])C(=O)[C@]([H])(C([H])([H])C(=C([H])[H])C([H])=O)[C@@]12C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O5/c1-5-6-7-8-17(2)9-12-24(29)30-23-11-10-19(16-27)25(4)20(13-18(3)15-26)22(28)14-21(23)25/h8-9,12,14-15,19-20,23,27H,3,5-7,10-11,13,16H2,1-2,4H3/b12-9+,17-8+/t19-,20-,23-,25+/m0/s1

> <INCHI_KEY>
KZXIDLYHAWGLBM-VCZIDFHPSA-N

> <FORMULA>
C25H34O5

> <MOLECULAR_WEIGHT>
414.542

> <EXACT_MASS>
414.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.478394817214124

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,7R,7aR)-7-(hydroxymethyl)-7a-methyl-1-(2-methylidene-3-oxopropyl)-2-oxo-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl (2E,4E)-4-methylnona-2,4-dienoate

> <ALOGPS_LOGP>
3.66

> <JCHEM_LOGP>
4.3210140730000015

> <ALOGPS_LOGS>
-5.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.47617734038473

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.373508229207584

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2780255000148895

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
120.13169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.60e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,7R,7aR)-7-(hydroxymethyl)-7a-methyl-1-(2-methylidene-3-oxopropyl)-2-oxo-4,5,6,7-tetrahydro-1H-inden-4-yl (2E,4E)-4-methylnona-2,4-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 65  0  0  0  0  0  0  0  0999 V2000
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  1  2  2  3
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 29  6  1  0
 29 10  1  0
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 30 63  1  0
 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      -3.362   1.305   2.385  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.235   1.528   1.409  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.595   0.969   1.584  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.925   0.318   2.586  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.897   2.307   0.211  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.146   1.681  -1.124  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.758   2.758  -2.111  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.422   3.780  -2.424  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.459   2.365  -2.622  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.194   1.137  -2.293  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.066   0.235  -2.528  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.334  -0.055  -1.352  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.999   0.156  -1.174  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.648   0.653  -2.139  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.618  -0.190   0.091  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.903  -0.009   0.325  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.599  -0.323   1.550  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.905  -0.910   2.701  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.893  -0.077   1.622  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.722  -0.349   2.811  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.825  -1.344   2.497  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.723  -0.810   1.418  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.367   0.500   1.856  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.530  -1.074  -3.100  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.939  -1.434  -2.940  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.939  -0.466  -2.445  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.065  -1.275  -1.844  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.105  -0.570  -1.327  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.334   0.539  -1.485  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.784  -0.236  -0.331  0.00  0.00           C+0
HETATM   31  H   UNK     0      -3.673   0.742   3.238  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.349   1.669   2.349  0.00  0.00           H+0
HETATM   33  H   UNK     0      -6.323   1.136   0.808  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.487   3.276   0.318  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.830   2.695   0.271  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.257   1.529  -1.181  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.805   3.041  -3.208  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.305   0.654  -3.229  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.012  -0.606   0.869  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.450   0.426  -0.530  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.521  -1.667   3.260  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.474  -0.146   3.391  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.030  -1.514   2.332  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.383   0.350   0.765  0.00  0.00           H+0
HETATM   45  H   UNK     0       6.255   0.618   3.068  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.159  -0.599   3.721  0.00  0.00           H+0
HETATM   47  H   UNK     0       6.376  -2.292   2.136  0.00  0.00           H+0
HETATM   48  H   UNK     0       7.447  -1.554   3.378  0.00  0.00           H+0
HETATM   49  H   UNK     0       7.149  -0.622   0.490  0.00  0.00           H+0
HETATM   50  H   UNK     0       8.518  -1.541   1.169  0.00  0.00           H+0
HETATM   51  H   UNK     0       8.456   0.465   2.964  0.00  0.00           H+0
HETATM   52  H   UNK     0       7.720   1.339   1.521  0.00  0.00           H+0
HETATM   53  H   UNK     0       9.386   0.578   1.383  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.319  -1.033  -4.215  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.808  -1.871  -2.764  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.964  -2.357  -2.273  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.369  -1.867  -3.911  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.376   0.094  -3.311  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.659  -2.049  -1.128  0.00  0.00           H+0
HETATM   60  H   UNK     0      -5.465  -1.891  -2.698  0.00  0.00           H+0
HETATM   61  H   UNK     0      -6.536  -1.143  -0.617  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.342  -1.217  -0.743  0.00  0.00           H+0
HETATM   63  H   UNK     0      -3.572  -0.603   0.335  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.009   0.273   0.232  0.00  0.00           H+0
CONECT    1    2   31   32                                                  
CONECT    2    1    3    5                                                  
CONECT    3    2    4   33                                                  
CONECT    4    3                                                            
CONECT    5    2    6   34   35                                             
CONECT    6    5    7   29   36                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   37                                                  
CONECT   10    9   11   29                                                  
CONECT   11   10   12   24   38                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   39                                                  
CONECT   16   15   17   40                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   41   42   43                                             
CONECT   19   17   20   44                                                  
CONECT   20   19   21   45   46                                             
CONECT   21   20   22   47   48                                             
CONECT   22   21   23   49   50                                             
CONECT   23   22   51   52   53                                             
CONECT   24   11   25   54   55                                             
CONECT   25   24   26   56   57                                             
CONECT   26   25   27   29   58                                             
CONECT   27   26   28   59   60                                             
CONECT   28   27   61                                                       
CONECT   29   26   30    6   10                                             
CONECT   30   29   62   63   64                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    5                                                            
CONECT   35    5                                                            
CONECT   36    6                                                            
CONECT   37    9                                                            
CONECT   38   11                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   18                                                            
CONECT   42   18                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   22                                                            
CONECT   51   23                                                            
CONECT   52   23                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   24                                                            
CONECT   56   25                                                            
CONECT   57   25                                                            
CONECT   58   26                                                            
CONECT   59   27                                                            
CONECT   60   27                                                            
CONECT   61   28                                                            
CONECT   62   30                                                            
CONECT   63   30                                                            
CONECT   64   30                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  130    0
END

RDKit          3D

64 65  0  0  0  0  0  0  0  0999 V2000
   -3.3620    1.3053    2.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354    1.5284    1.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5951    0.9687    1.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9250    0.3181    2.5862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8970    2.3069    0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1461    1.6811   -1.1244 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7583    2.7582   -2.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224    3.7803   -2.4241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4590    2.3653   -2.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1940    1.1365   -2.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0656    0.2345   -2.5280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3339   -0.0548   -1.3523 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9993    0.1558   -1.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6481    0.6527   -2.1394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6178   -0.1896    0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9031   -0.0090    0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.3233    1.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9046   -0.9099    2.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8931   -0.0770    1.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7216   -0.3490    2.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8254   -1.3440    2.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7229   -0.8099    1.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3667    0.5005    1.8564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5299   -1.0742   -3.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9391   -1.4338   -2.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9390   -0.4658   -2.4446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0648   -1.2751   -1.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1050   -0.5702   -1.3269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342    0.5386   -1.4849 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7835   -0.2360   -0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6726    0.7424    3.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3487    1.6691    2.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3229    1.1362    0.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4874    3.2759    0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8305    2.6951    0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2569    1.5290   -1.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8048    3.0413   -3.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3052    0.6541   -3.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125   -0.6057    0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4502    0.4262   -0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207   -1.6669    3.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740   -0.1456    3.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0301   -1.5140    2.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827    0.3495    0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2546    0.6182    3.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1588   -0.5986    3.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3757   -2.2918    2.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4466   -1.5543    3.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1489   -0.6223    0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5175   -1.5414    1.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4562    0.4650    2.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7203    1.3395    1.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3856    0.5781    1.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3186   -1.0326   -4.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8076   -1.8705   -2.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9642   -2.3569   -2.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3690   -1.8670   -3.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3758    0.0937   -3.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6589   -2.0486   -1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4655   -1.8914   -2.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5356   -1.1432   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3420   -1.2172   -0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718   -0.6027    0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0091    0.2725    0.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 11 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
 29 30  1  1
 29  6  1  0
 29 10  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  1
  9 37  1  0
 11 38  1  6
 15 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  6
 27 59  1  0
 27 60  1  0
 28 61  1  0
 30 62  1  0
 30 63  1  0
 30 64  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(1R,4S,7R,7AR)-7-(hydroxymethyl)-7a-methyl-1-(2-methylidene-3-oxopropyl)-2-oxo-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl (2E,4E)-4-methylnona-2,4-dienoic acid	Generator

Chemical Formula

C₂₅H₃₄O₅

Average Mass

414.5420 Da

Monoisotopic Mass

414.24062 Da

IUPAC Name

(1R,4S,7R,7aR)-7-(hydroxymethyl)-7a-methyl-1-(2-methylidene-3-oxopropyl)-2-oxo-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl (2E,4E)-4-methylnona-2,4-dienoate

Traditional Name

(1R,4S,7R,7aR)-7-(hydroxymethyl)-7a-methyl-1-(2-methylidene-3-oxopropyl)-2-oxo-4,5,6,7-tetrahydro-1H-inden-4-yl (2E,4E)-4-methylnona-2,4-dienoate

CAS Registry Number

Not Available

SMILES

CCCC\C=C(/C)\C=C\C(=O)O[C@H]1CC[C@@H](CO)[C@]2(C)[C@@H](CC(=C)C=O)C(=O)C=C12

InChI Identifier

InChI=1S/C25H34O5/c1-5-6-7-8-17(2)9-12-24(29)30-23-11-10-19(16-27)25(4)20(13-18(3)15-26)22(28)14-21(23)25/h8-9,12,14-15,19-20,23,27H,3,5-7,10-11,13,16H2,1-2,4H3/b12-9+,17-8+/t19-,20-,23-,25+/m0/s1

InChI Key

KZXIDLYHAWGLBM-VCZIDFHPSA-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
Dictyopanus	NPAtlas	11079807
Dictyopanus sp. HKI 0181	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Alpha,beta-unsaturated aldehyde
Enal
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Aldehyde
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.66	ALOGPS
logP	4.32	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	16.37	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	120.13 m³·mol⁻¹	ChemAxon
Polarizability	47.48 Å³	ChemAxon
Number of Rings	2	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

NPA007453

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8268773

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10093237

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dorfelt H, Schlegel B, Grafe U: Dictyopanines A, B and C, new bicyclic sesquiterpene esters from Dictyopanus sp. HKI 0181. J Antibiot (Tokyo). 2000 Aug;53(8):839-43. doi: 10.7164/antibiotics.53.839. [PubMed:11079807 ]

Showing NP-Card for Dictyopanine A (NP0003519)

MOL for NP0003519 (Dictyopanine A)

3D MOL for NP0003519 (Dictyopanine A)

3D SDF for NP0003519 (Dictyopanine A)

3D-SDF for NP0003519 (Dictyopanine A)

PDB for NP0003519 (Dictyopanine A)

3D PDB for NP0003519 (Dictyopanine A)

SMILES for NP0003519 (Dictyopanine A)

INCHI for NP0003519 (Dictyopanine A)

Structure for NP0003519 (Dictyopanine A)

3D Structure for NP0003519 (Dictyopanine A)