NP-MRD: Showing NP-Card for 18-acetyl-13,15-diene-19-cassanoic acid (NP0026507)

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Record Information

Version

2.0

Created at

2021-06-19 18:21:52 UTC

Updated at

2021-06-29 23:52:04 UTC

NP-MRD ID

NP0026507

Secondary Accession Numbers

None

Natural Product Identification

Common Name

18-acetyl-13,15-diene-19-cassanoic acid

Provided By

JEOL Database JEOL Logo

Description

18-acetyl-13,15-diene-19-cassanoic acid is found in Myrospermum frutescens. 18-acetyl-13,15-diene-19-cassanoic acid was first documented in 2003 (Mendoza, D. T., et al.). Based on a literature review very few articles have been published on CHEMBL459204.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120213D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306192120213D          

 58 60  0  0  0  0            999 V2000
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   -2.2881    1.8530    4.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1220    1.5493    0.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4863   -0.8835    1.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2318   -0.7186    1.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117   -0.6477   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6140   -2.0764   -0.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5129   -0.9544   -1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3313   -3.2401   -2.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182   -3.3587   -3.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -6.0398   -0.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6889   -4.4809    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8276   -4.6178   -1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902   -0.8103   -5.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9750   -1.3834   -4.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7965   -1.3329   -3.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3619    0.9973   -4.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0855    0.7747   -4.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564    0.9672   -1.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1726    2.3507   -2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3551    1.4742   -1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5179    1.4345   -3.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2686    2.7808   -2.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8817    0.9685    0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6360    3.5653   -0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0526    3.3196   -0.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7397    2.9745    1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    4.3947    1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0  0  0  0
 20 21  1  0  0  0  0
 19 10  1  0  0  0  0
 22 23  1  6  0  0  0
  9  8  1  0  0  0  0
  6 33  1  6  0  0  0
 24 22  1  0  0  0  0
  8  7  1  0  0  0  0
 24 54  1  1  0  0  0
  7  6  1  0  0  0  0
  3  2  1  0  0  0  0
 24  6  1  0  0  0  0
  2  1  2  3  0  0  0
 10  9  1  0  0  0  0
  4  5  1  0  0  0  0
 22 21  1  0  0  0  0
 10 16  1  6  0  0  0
 22  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 24 25  1  0  0  0  0
 16 18  1  0  0  0  0
  6  4  1  0  0  0  0
 16 17  2  0  0  0  0
  3 26  1  0  0  0  0
 12 13  1  0  0  0  0
 26 25  1  0  0  0  0
 13 14  1  0  0  0  0
  3  4  2  0  0  0  0
 13 15  2  0  0  0  0
 20 47  1  0  0  0  0
 20 48  1  0  0  0  0
 19 45  1  0  0  0  0
 19 46  1  0  0  0  0
 21 49  1  0  0  0  0
 21 50  1  0  0  0  0
  9 38  1  1  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
 26 57  1  0  0  0  0
 26 58  1  0  0  0  0
 25 55  1  0  0  0  0
 25 56  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
  2 29  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  5 30  1  0  0  0  0
  5 31  1  0  0  0  0
  5 32  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 18 44  1  0  0  0  0
 14 41  1  0  0  0  0
 14 42  1  0  0  0  0
 14 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026507

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]1(C([H])([H])OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]3([H])C([H])([H])C([H])([H])C(C([H])=C([H])[H])=C(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])[C@@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O4/c1-5-16-7-9-18-17(14(16)2)8-10-19-21(18,4)11-6-12-22(19,20(24)25)13-26-15(3)23/h5,17-19H,1,6-13H2,2-4H3,(H,24,25)/t17-,18-,19+,21+,22+/m0/s1

> <INCHI_KEY>
MMAYUYRWDRFNKQ-JIWOIOHBSA-N

> <FORMULA>
C22H32O4

> <MOLECULAR_WEIGHT>
360.494

> <EXACT_MASS>
360.23005951

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.27498545305079

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4aR,4bS,8aR,10aR)-1-[(acetyloxy)methyl]-7-ethenyl-4a,8-dimethyl-1,2,3,4,4a,4b,5,6,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid

> <ALOGPS_LOGP>
4.17

> <JCHEM_LOGP>
4.170852984333334

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.510089443352802

> <JCHEM_PKA_STRONGEST_BASIC>
-6.996177251081641

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
101.06790000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aR,4bS,8aR,10aR)-1-[(acetyloxy)methyl]-7-ethenyl-4a,8-dimethyl-2,3,4,4b,5,6,8a,9,10,10a-decahydrophenanthrene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    0.9226    4.0975    4.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0651    3.1455    3.9033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1559    2.6666    2.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0672    1.7050    2.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798    1.1682    3.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1994    1.1153    0.8193 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3616   -0.4168    0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5477   -0.9877   -0.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3927   -0.5930   -1.5232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3763   -1.3377   -2.9096 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3712   -2.8819   -2.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812   -3.2956   -1.8603 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7623   -4.6409   -1.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8771   -4.9577   -0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0381   -5.4754   -2.1936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6270   -1.0837   -3.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7799   -1.0716   -3.3484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3968   -0.9307   -5.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295   -0.9329   -3.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1153    0.5744   -3.7752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710    1.2733   -2.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2093    0.9694   -1.5927 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4029    1.6942   -2.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0116    1.4845   -0.1128 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2627    2.9840    0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7005    3.3020    1.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5636    4.6443    3.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0045    4.3530    5.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4983    2.6642    4.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7415    0.2136    3.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0471    1.0149    2.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2881    1.8530    4.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1220    1.5493    0.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4863   -0.8835    1.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2318   -0.7186    1.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117   -0.6477   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6140   -2.0764   -0.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5129   -0.9544   -1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3313   -3.2401   -2.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182   -3.3587   -3.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -6.0398   -0.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6889   -4.4809    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8276   -4.6178   -1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902   -0.8103   -5.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9750   -1.3834   -4.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7965   -1.3329   -3.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3619    0.9973   -4.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0855    0.7747   -4.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564    0.9672   -1.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1726    2.3507   -2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3551    1.4742   -1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5179    1.4345   -3.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2686    2.7808   -2.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8817    0.9685    0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6360    3.5653   -0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0526    3.3196   -0.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7397    2.9745    1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    4.3947    1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 20 21  1  0
 19 10  1  0
 22 23  1  6
  9  8  1  0
  6 33  1  6
 24 22  1  0
  8  7  1  0
 24 54  1  1
  7  6  1  0
  3  2  1  0
 24  6  1  0
  2  1  2  3
 10  9  1  0
  4  5  1  0
 22 21  1  0
 10 16  1  6
 22  9  1  0
 10 11  1  0
 11 12  1  0
 24 25  1  0
 16 18  1  0
  6  4  1  0
 16 17  2  0
  3 26  1  0
 12 13  1  0
 26 25  1  0
 13 14  1  0
  3  4  2  0
 13 15  2  0
 20 47  1  0
 20 48  1  0
 19 45  1  0
 19 46  1  0
 21 49  1  0
 21 50  1  0
  9 38  1  1
  8 36  1  0
  8 37  1  0
  7 34  1  0
  7 35  1  0
 26 57  1  0
 26 58  1  0
 25 55  1  0
 25 56  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
  2 29  1  0
  1 27  1  0
  1 28  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
 11 39  1  0
 11 40  1  0
 18 44  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.923   4.098   4.297  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.065   3.146   3.903  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.156   2.667   2.537  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.067   1.705   2.236  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.080   1.168   3.226  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.199   1.115   0.819  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.362  -0.417   0.823  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.548  -0.988  -0.584  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.393  -0.593  -1.523  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.376  -1.338  -2.910  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.371  -2.882  -2.747  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.681  -3.296  -1.860  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.762  -4.641  -1.671  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.877  -4.958  -0.722  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.038  -5.475  -2.194  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.627  -1.084  -3.749  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.780  -1.072  -3.348  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.397  -0.931  -5.066  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.930  -0.933  -3.647  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.115   0.574  -3.775  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.071   1.273  -2.420  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.209   0.969  -1.593  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.403   1.694  -2.258  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.012   1.484  -0.113  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.263   2.984   0.027  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.701   3.302   1.456  0.00  0.00           C+0
HETATM   27  H   UNK     0       1.564   4.644   3.616  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.004   4.353   5.349  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.498   2.664   4.699  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.742   0.214   3.640  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.047   1.015   2.734  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.288   1.853   4.052  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.122   1.549   0.412  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.486  -0.884   1.294  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.232  -0.719   1.417  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.512  -0.648  -0.972  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.614  -2.076  -0.490  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.513  -0.954  -1.008  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.331  -3.240  -2.354  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.218  -3.359  -3.725  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.929  -6.040  -0.572  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.689  -4.481   0.243  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.828  -4.618  -1.141  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.290  -0.810  -5.453  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.975  -1.383  -4.646  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.797  -1.333  -3.104  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.362   0.997  -4.447  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.086   0.775  -4.246  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.956   0.967  -1.847  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.173   2.351  -2.594  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.355   1.474  -1.769  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.518   1.435  -3.312  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.269   2.781  -2.236  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.882   0.969   0.276  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.636   3.565  -0.214  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.053   3.320  -0.652  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.740   2.974   1.593  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.686   4.395   1.552  0.00  0.00           H+0
CONECT    1    2   27   28                                                  
CONECT    2    3    1   29                                                  
CONECT    3    2   26    4                                                  
CONECT    4    5    6    3                                                  
CONECT    5    4   30   31   32                                             
CONECT    6   33    7   24    4                                             
CONECT    7    8    6   34   35                                             
CONECT    8    9    7   36   37                                             
CONECT    9    8   10   22   38                                             
CONECT   10   19    9   16   11                                             
CONECT   11   10   12   39   40                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13   41   42   43                                             
CONECT   15   13                                                            
CONECT   16   10   18   17                                                  
CONECT   17   16                                                            
CONECT   18   16   44                                                       
CONECT   19   20   10   45   46                                             
CONECT   20   19   21   47   48                                             
CONECT   21   20   22   49   50                                             
CONECT   22   23   24   21    9                                             
CONECT   23   22   51   52   53                                             
CONECT   24   22   54    6   25                                             
CONECT   25   24   26   55   56                                             
CONECT   26    3   25   57   58                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    2                                                            
CONECT   30    5                                                            
CONECT   31    5                                                            
CONECT   32    5                                                            
CONECT   33    6                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    8                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   14                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   18                                                            
CONECT   45   19                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   20                                                            
CONECT   49   21                                                            
CONECT   50   21                                                            
CONECT   51   23                                                            
CONECT   52   23                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  120    0
END

RDKit          3D

58 60  0  0  0  0  0  0  0  0999 V2000
    0.9226    4.0975    4.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0651    3.1455    3.9033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1559    2.6666    2.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0672    1.7050    2.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798    1.1682    3.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1994    1.1153    0.8193 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3616   -0.4168    0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5477   -0.9877   -0.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3927   -0.5930   -1.5232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3763   -1.3377   -2.9096 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3712   -2.8819   -2.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812   -3.2956   -1.8603 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7623   -4.6409   -1.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8771   -4.9577   -0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0381   -5.4754   -2.1936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6270   -1.0837   -3.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7799   -1.0716   -3.3484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3968   -0.9307   -5.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295   -0.9329   -3.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1153    0.5744   -3.7752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710    1.2733   -2.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2093    0.9694   -1.5927 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4029    1.6942   -2.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0116    1.4845   -0.1128 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2627    2.9840    0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7005    3.3020    1.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5636    4.6443    3.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0045    4.3530    5.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4983    2.6642    4.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7415    0.2136    3.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0471    1.0149    2.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2881    1.8530    4.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1220    1.5493    0.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4863   -0.8835    1.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2318   -0.7186    1.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117   -0.6477   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6140   -2.0764   -0.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5129   -0.9544   -1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3313   -3.2401   -2.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182   -3.3587   -3.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -6.0398   -0.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6889   -4.4809    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8276   -4.6178   -1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902   -0.8103   -5.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9750   -1.3834   -4.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7965   -1.3329   -3.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3619    0.9973   -4.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0855    0.7747   -4.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564    0.9672   -1.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1726    2.3507   -2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3551    1.4742   -1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5179    1.4345   -3.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2686    2.7808   -2.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8817    0.9685    0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6360    3.5653   -0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0526    3.3196   -0.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7397    2.9745    1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    4.3947    1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 20 21  1  0
 19 10  1  0
 22 23  1  6
  9  8  1  0
  6 33  1  6
 24 22  1  0
  8  7  1  0
 24 54  1  1
  7  6  1  0
  3  2  1  0
 24  6  1  0
  2  1  2  3
 10  9  1  0
  4  5  1  0
 22 21  1  0
 10 16  1  6
 22  9  1  0
 10 11  1  0
 11 12  1  0
 24 25  1  0
 16 18  1  0
  6  4  1  0
 16 17  2  0
  3 26  1  0
 12 13  1  0
 26 25  1  0
 13 14  1  0
  3  4  2  0
 13 15  2  0
 20 47  1  0
 20 48  1  0
 19 45  1  0
 19 46  1  0
 21 49  1  0
 21 50  1  0
  9 38  1  1
  8 36  1  0
  8 37  1  0
  7 34  1  0
  7 35  1  0
 26 57  1  0
 26 58  1  0
 25 55  1  0
 25 56  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
  2 29  1  0
  1 27  1  0
  1 28  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
 11 39  1  0
 11 40  1  0
 18 44  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₂O₄

Average Mass

360.4940 Da

Monoisotopic Mass

360.23006 Da

IUPAC Name

(1S,4aR,4bS,8aR,10aR)-1-[(acetyloxy)methyl]-7-ethenyl-4a,8-dimethyl-1,2,3,4,4a,4b,5,6,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid

Traditional Name

(1S,4aR,4bS,8aR,10aR)-1-[(acetyloxy)methyl]-7-ethenyl-4a,8-dimethyl-2,3,4,4b,5,6,8a,9,10,10a-decahydrophenanthrene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@@]1(C([H])([H])OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]3([H])C([H])([H])C([H])([H])C(C([H])=C([H])[H])=C(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])[C@@]12[H]

InChI Identifier

InChI=1S/C22H32O4/c1-5-16-7-9-18-17(14(16)2)8-10-19-21(18,4)11-6-12-22(19,20(24)25)13-26-15(3)23/h5,17-19H,1,6-13H2,2-4H3,(H,24,25)/t17-,18-,19+,21+,22+/m0/s1

InChI Key

MMAYUYRWDRFNKQ-JIWOIOHBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Myrospermum frutescens	JEOL database	Mendoza, D. T., et al, J. Nat. Prod. 66, 928 (2003)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Isocopalane and spongiane diterpenoids

Alternative Parents

Substituents

Isocopalane diterpenoid
Phenanthrene
Hydrophenanthrene
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
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	4.17	ALOGPS
logP	4.17	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.51	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	101.07 m³·mol⁻¹	ChemAxon
Polarizability	41.27 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

10286590

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21674169

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mendoza, D. T., et al. (2003). Mendoza, D. T., et al, J. Nat. Prod. 66, 928 (2003). J. Nat. Prod..

Showing NP-Card for 18-acetyl-13,15-diene-19-cassanoic acid (NP0026507)

MOL for NP0026507 (18-acetyl-13,15-diene-19-cassanoic acid)

3D MOL for NP0026507 (18-acetyl-13,15-diene-19-cassanoic acid)

3D SDF for NP0026507 (18-acetyl-13,15-diene-19-cassanoic acid)

3D-SDF for NP0026507 (18-acetyl-13,15-diene-19-cassanoic acid)

PDB for NP0026507 (18-acetyl-13,15-diene-19-cassanoic acid)

3D PDB for NP0026507 (18-acetyl-13,15-diene-19-cassanoic acid)

SMILES for NP0026507 (18-acetyl-13,15-diene-19-cassanoic acid)

INCHI for NP0026507 (18-acetyl-13,15-diene-19-cassanoic acid)

Structure for NP0026507 (18-acetyl-13,15-diene-19-cassanoic acid)

3D Structure for NP0026507 (18-acetyl-13,15-diene-19-cassanoic acid)