NP-MRD: Showing NP-Card for 2,3-secodicarboxylpregn-17-en-16-one (NP0035269)

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Record Information

Version

1.0

Created at

2021-06-20 18:45:42 UTC

Updated at

2021-06-30 00:06:09 UTC

NP-MRD ID

NP0035269

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-secodicarboxylpregn-17-en-16-one

Provided By

JEOL Database JEOL Logo

Description

2-[(3Z,3aS,5aS,6S,7S,9aR,9bS)-6-(carboxymethyl)-3-ethylidene-3a,6-dimethyl-2-oxo-dodecahydro-1H-cyclopenta[a]naphthalen-7-yl]acetic acid belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. 2,3-secodicarboxylpregn-17-en-16-one is found in Melia azedarach. It was first documented in 2002 (PMID: 33651529). Based on a literature review very few articles have been published on 2-[(3Z,3aS,5aS,6S,7S,9aR,9bS)-6-(carboxymethyl)-3-ethylidene-3a,6-dimethyl-2-oxo-dodecahydro-1H-cyclopenta[a]naphthalen-7-yl]acetic acid (PMID: 33079503) (PMID: 26389513) (PMID: 26389498) (PMID: 26389454).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120453D          

 56 58  0  0  0  0            999 V2000
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   -2.9219   -2.8079    2.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6123   -4.5499    0.3774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4797   -2.5435   -0.3581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4469   -1.2310    0.4258 C   0  0  1  0  0  0  0  0  0  0  0  0
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  2  1  1  0  0  0  0
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  9 10  1  0  0  0  0
 22 16  1  0  0  0  0
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  3 25  1  0  0  0  0
 19 21  1  0  0  0  0
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  4  5  2  0  0  0  0
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  3  2  2  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202120453D          

 56 58  0  0  0  0            999 V2000
   -3.1670   -4.1935    3.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -2.8079    2.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8794   -2.4270   -1.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2118   -1.4164    1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5483    0.2645   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715   -0.5829   -0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4771   -1.0324   -1.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5293    1.2683   -2.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1129    0.7688   -1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7764    1.8926    0.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4079    3.5438   -2.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7043    4.3293   -0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8119    3.8473   -2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1850    3.9880   -1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3846    2.3593   -1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2050    3.3496   -0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1140    4.6157    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1775    3.8929    1.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4621    3.6167    2.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8206    0.9056    1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772    1.8258    0.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565    2.0889    2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2166   -0.2332    2.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8335    0.2852    2.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280   -0.5824    0.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7119    0.2598   -0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0036   -1.4523   -0.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  9  8  1  0  0  0  0
 22 23  1  0  0  0  0
  8  7  1  0  0  0  0
 25 24  1  0  0  0  0
  7  6  1  0  0  0  0
  9 10  1  0  0  0  0
 22 16  1  0  0  0  0
 16 11  1  0  0  0  0
 11 10  1  0  0  0  0
  6  4  1  0  0  0  0
 16 18  1  1  0  0  0
  4  3  1  0  0  0  0
 18 19  1  0  0  0  0
  3 25  1  0  0  0  0
 19 21  1  0  0  0  0
 24 23  1  0  0  0  0
 19 20  2  0  0  0  0
  4  5  2  0  0  0  0
 11 12  1  0  0  0  0
 25  7  1  0  0  0  0
 12 13  1  0  0  0  0
  3  2  2  0  0  0  0
 13 15  1  0  0  0  0
 13 14  2  0  0  0  0
 25 26  1  6  0  0  0
 16 17  1  0  0  0  0
 22  8  1  0  0  0  0
 11 39  1  1  0  0  0
 22 49  1  1  0  0  0
  8 34  1  6  0  0  0
 24 52  1  0  0  0  0
 24 53  1  0  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
  7 33  1  1  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
  2 30  1  0  0  0  0
 26 54  1  0  0  0  0
 26 55  1  0  0  0  0
 26 56  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  9 35  1  0  0  0  0
  9 36  1  0  0  0  0
 10 37  1  0  0  0  0
 10 38  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 21 48  1  0  0  0  0
 12 40  1  0  0  0  0
 12 41  1  0  0  0  0
 15 42  1  0  0  0  0
 17 43  1  0  0  0  0
 17 44  1  0  0  0  0
 17 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035269

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@]1([H])C([H])([H])C([H])([H])[C@@]2([H])[C@]3([H])C([H])([H])C(=O)\C(=C(\[H])C([H])([H])[H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2([H])[C@@]1(C([H])([H])[H])C([H])([H])C(=O)O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O5/c1-4-14-17(22)10-16-13-6-5-12(9-18(23)24)21(3,11-19(25)26)15(13)7-8-20(14,16)2/h4,12-13,15-16H,5-11H2,1-3H3,(H,23,24)(H,25,26)/b14-4+/t12-,13+,15-,16-,20+,21-/m0/s1

> <INCHI_KEY>
OYIPETGGBDETFA-JAQDNKOBSA-N

> <FORMULA>
C21H30O5

> <MOLECULAR_WEIGHT>
362.466

> <EXACT_MASS>
362.209324066

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.035125948453356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3Z,3aS,5aS,6S,7S,9aR,9bS)-7-(carboxymethyl)-3-ethylidene-3a,6-dimethyl-2-oxo-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]acetic acid

> <ALOGPS_LOGP>
3.30

> <JCHEM_LOGP>
3.3032537163333338

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.779134559897088

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.106713475050452

> <JCHEM_PKA_STRONGEST_BASIC>
-4.861130371659753

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
97.27199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3Z,3aS,5aS,6S,7S,9aR,9bS)-7-(carboxymethyl)-3-ethylidene-3a,6-dimethyl-2-oxo-octahydro-1H-cyclopenta[a]naphthalen-6-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
   -3.1670   -4.1935    3.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -2.8079    2.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1871   -2.4406    1.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4378   -3.3474    0.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6123   -4.5499    0.3774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4797   -2.5435   -0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4469   -1.2310    0.4258 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1029    0.0193   -0.2777 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5068   -0.2357   -0.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0997    1.0111   -1.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1409    2.2066   -0.4975 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8324    3.4009   -1.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3233    3.2095   -1.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    2.4331   -0.7250 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536    4.0530   -2.2456 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7139    2.5337    0.1006 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2224    3.0779   -1.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8062    3.6641    1.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7330    3.3713    2.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4711    2.7108    3.3155 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9544    3.9107    2.1555 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1234    1.2072    0.7338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2502    1.3866    1.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8331    0.0826    2.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8872   -1.0315    0.9523 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9302   -0.6820   -0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9952   -4.2200    4.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2071   -4.4786    2.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5148   -4.9465    2.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060   -2.0300    3.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5016   -3.0241   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8794   -2.4270   -1.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2118   -1.4164    1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5483    0.2645   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715   -0.5829   -0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4771   -1.0324   -1.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5293    1.2683   -2.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1129    0.7688   -1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7764    1.8926    0.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4079    3.5438   -2.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7043    4.3293   -0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8119    3.8473   -2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1850    3.9880   -1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3846    2.3593   -1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2050    3.3496   -0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1140    4.6157    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1775    3.8929    1.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4621    3.6167    2.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8206    0.9056    1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772    1.8258    0.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565    2.0889    2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2166   -0.2332    2.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8335    0.2852    2.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280   -0.5824    0.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7119    0.2598   -0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0036   -1.4523   -0.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  9  8  1  0
 22 23  1  0
  8  7  1  0
 25 24  1  0
  7  6  1  0
  9 10  1  0
 22 16  1  0
 16 11  1  0
 11 10  1  0
  6  4  1  0
 16 18  1  1
  4  3  1  0
 18 19  1  0
  3 25  1  0
 19 21  1  0
 24 23  1  0
 19 20  2  0
  4  5  2  0
 11 12  1  0
 25  7  1  0
 12 13  1  0
  3  2  2  0
 13 15  1  0
 13 14  2  0
 25 26  1  6
 16 17  1  0
 22  8  1  0
 11 39  1  1
 22 49  1  1
  8 34  1  6
 24 52  1  0
 24 53  1  0
 23 50  1  0
 23 51  1  0
  7 33  1  1
  6 31  1  0
  6 32  1  0
  2 30  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 18 46  1  0
 18 47  1  0
 21 48  1  0
 12 40  1  0
 12 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.167  -4.194   3.001  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.922  -2.808   2.496  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.187  -2.441   1.435  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.438  -3.347   0.489  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.612  -4.550   0.377  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.480  -2.543  -0.358  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.447  -1.231   0.426  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.103   0.019  -0.278  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.507  -0.236  -0.833  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.100   1.011  -1.472  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.141   2.207  -0.498  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.832   3.401  -1.198  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.323   3.209  -1.338  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.035   2.433  -0.725  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.854   4.053  -2.246  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.714   2.534   0.101  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.222   3.078  -1.010  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.806   3.664   1.174  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.733   3.371   2.325  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.471   2.711   3.316  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.954   3.911   2.155  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.123   1.207   0.734  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.250   1.387   1.436  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.833   0.083   2.009  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.887  -1.032   0.952  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.930  -0.682  -0.136  0.00  0.00           C+0
HETATM   27  H   UNK     0      -2.995  -4.220   4.083  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.207  -4.479   2.817  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.515  -4.947   2.557  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.406  -2.030   3.083  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.502  -3.024  -0.382  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.879  -2.427  -1.369  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.212  -1.416   1.293  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.548   0.265  -1.123  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.172  -0.583  -0.032  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.477  -1.032  -1.586  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.529   1.268  -2.373  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.113   0.769  -1.815  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.776   1.893   0.342  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.408   3.544  -2.198  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.704   4.329  -0.637  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.812   3.847  -2.229  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.185   3.988  -1.464  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.385   2.359  -1.817  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.205   3.350  -0.611  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.114   4.616   0.724  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.178   3.893   1.600  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.462   3.617   2.942  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.821   0.906   1.530  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.977   1.826   0.747  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.157   2.089   2.271  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.217  -0.233   2.861  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.833   0.285   2.411  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.928  -0.582   0.309  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.712   0.260  -0.647  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.004  -1.452  -0.912  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3   30                                                  
CONECT    3    4   25    2                                                  
CONECT    4    6    3    5                                                  
CONECT    5    4                                                            
CONECT    6    7    4   31   32                                             
CONECT    7    8    6   25   33                                             
CONECT    8    9    7   22   34                                             
CONECT    9    8   10   35   36                                             
CONECT   10    9   11   37   38                                             
CONECT   11   16   10   12   39                                             
CONECT   12   11   13   40   41                                             
CONECT   13   12   15   14                                                  
CONECT   14   13                                                            
CONECT   15   13   42                                                       
CONECT   16   22   11   18   17                                             
CONECT   17   16   43   44   45                                             
CONECT   18   16   19   46   47                                             
CONECT   19   18   21   20                                                  
CONECT   20   19                                                            
CONECT   21   19   48                                                       
CONECT   22   23   16    8   49                                             
CONECT   23   22   24   50   51                                             
CONECT   24   25   23   52   53                                             
CONECT   25   24    3    7   26                                             
CONECT   26   25   54   55   56                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    2                                                            
CONECT   31    6                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    8                                                            
CONECT   35    9                                                            
CONECT   36    9                                                            
CONECT   37   10                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   15                                                            
CONECT   43   17                                                            
CONECT   44   17                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
CONECT   52   24                                                            
CONECT   53   24                                                            
CONECT   54   26                                                            
CONECT   55   26                                                            
CONECT   56   26                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

RDKit          3D

56 58  0  0  0  0  0  0  0  0999 V2000
   -3.1670   -4.1935    3.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -2.8079    2.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1871   -2.4406    1.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4378   -3.3474    0.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6123   -4.5499    0.3774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4797   -2.5435   -0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4469   -1.2310    0.4258 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1029    0.0193   -0.2777 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5068   -0.2357   -0.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0997    1.0111   -1.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1409    2.2066   -0.4975 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8324    3.4009   -1.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3233    3.2095   -1.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    2.4331   -0.7250 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536    4.0530   -2.2456 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7139    2.5337    0.1006 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2224    3.0779   -1.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8062    3.6641    1.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7330    3.3713    2.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4711    2.7108    3.3155 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9544    3.9107    2.1555 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1234    1.2072    0.7338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2502    1.3866    1.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8331    0.0826    2.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8872   -1.0315    0.9523 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9302   -0.6820   -0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9952   -4.2200    4.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2071   -4.4786    2.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5148   -4.9465    2.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060   -2.0300    3.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5016   -3.0241   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8794   -2.4270   -1.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2118   -1.4164    1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5483    0.2645   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715   -0.5829   -0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4771   -1.0324   -1.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5293    1.2683   -2.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1129    0.7688   -1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7764    1.8926    0.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4079    3.5438   -2.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7043    4.3293   -0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8119    3.8473   -2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1850    3.9880   -1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3846    2.3593   -1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2050    3.3496   -0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1140    4.6157    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1775    3.8929    1.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4621    3.6167    2.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8206    0.9056    1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772    1.8258    0.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565    2.0889    2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2166   -0.2332    2.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8335    0.2852    2.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280   -0.5824    0.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7119    0.2598   -0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0036   -1.4523   -0.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  9  8  1  0
 22 23  1  0
  8  7  1  0
 25 24  1  0
  7  6  1  0
  9 10  1  0
 22 16  1  0
 16 11  1  0
 11 10  1  0
  6  4  1  0
 16 18  1  1
  4  3  1  0
 18 19  1  0
  3 25  1  0
 19 21  1  0
 24 23  1  0
 19 20  2  0
  4  5  2  0
 11 12  1  0
 25  7  1  0
 12 13  1  0
  3  2  2  0
 13 15  1  0
 13 14  2  0
 25 26  1  6
 16 17  1  0
 22  8  1  0
 11 39  1  1
 22 49  1  1
  8 34  1  6
 24 52  1  0
 24 53  1  0
 23 50  1  0
 23 51  1  0
  7 33  1  1
  6 31  1  0
  6 32  1  0
  2 30  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 18 46  1  0
 18 47  1  0
 21 48  1  0
 12 40  1  0
 12 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
M  END

View in JSmol

Synonyms

Value	Source
2-[(3Z,3AS,5as,6S,7S,9ar,9BS)-6-(carboxymethyl)-3-ethylidene-3a,6-dimethyl-2-oxo-dodecahydro-1H-cyclopenta[a]naphthalen-7-yl]acetate	Generator

Chemical Formula

C₂₁H₃₀O₅

Average Mass

362.4660 Da

Monoisotopic Mass

362.20932 Da

IUPAC Name

2-[(3Z,3aS,5aS,6S,7S,9aR,9bS)-7-(carboxymethyl)-3-ethylidene-3a,6-dimethyl-2-oxo-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]acetic acid

Traditional Name

[(3Z,3aS,5aS,6S,7S,9aR,9bS)-7-(carboxymethyl)-3-ethylidene-3a,6-dimethyl-2-oxo-octahydro-1H-cyclopenta[a]naphthalen-6-yl]acetic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])[C@]1([H])C([H])([H])C([H])([H])[C@@]2([H])[C@]3([H])C([H])([H])C(=O)\C(=C(\[H])C([H])([H])[H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2([H])[C@@]1(C([H])([H])[H])C([H])([H])C(=O)O[H]

InChI Identifier

InChI=1S/C21H30O5/c1-4-14-17(22)10-16-13-6-5-12(9-18(23)24)21(3,11-19(25)26)15(13)7-8-20(14,16)2/h4,12-13,15-16H,5-11H2,1-3H3,(H,23,24)(H,25,26)/b14-4+/t12-,13+,15-,16-,20+,21-/m0/s1

InChI Key

OYIPETGGBDETFA-JAQDNKOBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melia azedarach	JEOL database	Tan, Q. -G., et al, J. Nat. Prod. 73, 693 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Cyclic ketone
Ketone
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.3	ALOGPS
logP	3.3	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.27 m³·mol⁻¹	ChemAxon
Polarizability	40.04 Å³	ChemAxon
Number of Rings	3	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46211340

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Curcumin (Curcuma, Turmeric) and Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:33651529 ]
Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Health Professional Version. 2002. [PubMed:33079503 ]
Authors unspecified: Planning the Transition to End-of-Life Care in Advanced Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:26389513 ]
Authors unspecified: Childhood Central Nervous System Germ Cell Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389498 ]
Authors unspecified: Childhood Acute Myeloid Leukemia/Other Myeloid Malignancies Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389454 ]
Tan, Q. -G., et al. (2010). Tan, Q. -G., et al, J. Nat. Prod. 73, 693 (2010). J. Nat. Prod..

Showing NP-Card for 2,3-secodicarboxylpregn-17-en-16-one (NP0035269)

MOL for NP0035269 (2,3-secodicarboxylpregn-17-en-16-one)

3D MOL for NP0035269 (2,3-secodicarboxylpregn-17-en-16-one)

3D SDF for NP0035269 (2,3-secodicarboxylpregn-17-en-16-one)

3D-SDF for NP0035269 (2,3-secodicarboxylpregn-17-en-16-one)

PDB for NP0035269 (2,3-secodicarboxylpregn-17-en-16-one)

3D PDB for NP0035269 (2,3-secodicarboxylpregn-17-en-16-one)

SMILES for NP0035269 (2,3-secodicarboxylpregn-17-en-16-one)

INCHI for NP0035269 (2,3-secodicarboxylpregn-17-en-16-one)

Structure for NP0035269 (2,3-secodicarboxylpregn-17-en-16-one)

3D Structure for NP0035269 (2,3-secodicarboxylpregn-17-en-16-one)