NP-MRD: Showing NP-Card for (-)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene (NP0042721)

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Record Information

Version

2.0

Created at

2021-06-21 00:18:42 UTC

Updated at

2021-06-30 00:17:58 UTC

NP-MRD ID

NP0042721

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene

Provided By

JEOL Database JEOL Logo

Description

(5S,8S,10R,14R)-6beta-Acetoxycassa-12,15-diene 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. (-)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene is found in Caesalpinia platyloba. (-)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene was first documented in 2013 (Gomez-Hurtado, M. A., et al.). Based on a literature review very few articles have been published on (5S,8S,10R,14R)-6beta-Acetoxycassa-12,15-diene.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102183D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306212102183D          

 58 60  0  0  0  0            999 V2000
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   -1.1388    4.8848   -1.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9438    2.6213   -0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3577    2.6670   -2.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520    1.4227   -1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2521    1.9783    1.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5518    0.5524   -0.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4024    0.9067    1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9099   -1.4582    0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5187   -1.0751    5.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7681   -1.6545    4.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4648    0.1069    4.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9648   -0.8498   -1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6518   -3.4690    0.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8012   -4.4090   -1.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7467   -2.9993   -1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9687   -2.6849    0.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4377   -3.0054    1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1205   -4.1791    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4299   -3.6536   -1.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3342   -2.5420   -2.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8853   -1.7714   -1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6196   -1.7742   -3.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8854   -0.0609   -2.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    0.4991   -2.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7815    0.7667    0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5277    0.7406    1.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2603   -0.7485    0.7916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1038    3.4032    1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2411    4.0424   -1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5841    2.4179   -0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4237    2.6804   -1.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 22  1  1  0  0  0
  3 23  1  0  0  0  0
  4  3  2  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  0  0  0  0
 21  6  1  0  0  0  0
 14  9  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  2  3  0  0  0
  9  8  1  0  0  0  0
 15 16  1  6  0  0  0
  8  7  1  0  0  0  0
  9 10  1  0  0  0  0
 18 15  1  0  0  0  0
  7 32  1  1  0  0  0
 15 14  1  0  0  0  0
 23 24  1  0  0  0  0
  6  7  1  0  0  0  0
 15 17  1  0  0  0  0
  7 23  1  0  0  0  0
  6 31  1  6  0  0  0
 21 20  1  0  0  0  0
 14 39  1  6  0  0  0
  4  5  1  0  0  0  0
 10 11  1  0  0  0  0
  5  6  1  0  0  0  0
 11 13  2  0  0  0  0
 21 14  1  0  0  0  0
 11 12  1  0  0  0  0
  9 35  1  1  0  0  0
 19 48  1  0  0  0  0
 19 49  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 20 50  1  0  0  0  0
 20 51  1  0  0  0  0
  8 33  1  0  0  0  0
  8 34  1  0  0  0  0
  5 29  1  0  0  0  0
  5 30  1  0  0  0  0
 22 52  1  0  0  0  0
 22 53  1  0  0  0  0
 22 54  1  0  0  0  0
 23 55  1  1  0  0  0
  4 28  1  0  0  0  0
  2 27  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
 24 56  1  0  0  0  0
 24 57  1  0  0  0  0
 24 58  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
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042721

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C([H])C1=C([H])C([H])([H])[C@@]2([H])[C@@]([H])(C([H])([H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]3([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]23C([H])([H])[H])[C@@]1([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O2/c1-7-16-9-10-18-17(14(16)2)13-19(24-15(3)23)20-21(4,5)11-8-12-22(18,20)6/h7,9,14,17-20H,1,8,10-13H2,2-6H3/t14-,17-,18-,19+,20-,22+/m0/s1

> <INCHI_KEY>
HYHIOWBLMCOLTB-QBUJOIIVSA-N

> <FORMULA>
C22H34O2

> <MOLECULAR_WEIGHT>
330.512

> <EXACT_MASS>
330.255880335

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
39.79225399938635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4aS,4bR,8aS,9R,10aS)-2-ethenyl-1,4b,8,8-tetramethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-9-yl acetate

> <ALOGPS_LOGP>
5.36

> <JCHEM_LOGP>
4.994824569666667

> <ALOGPS_LOGS>
-5.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.003287046725093

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
99.43509999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.29e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aS,4bR,8aS,9R,10aS)-2-ethenyl-1,4b,8,8-tetramethyl-1,4,4a,5,6,7,8a,9,10,10a-decahydrophenanthren-9-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    2.1899    6.1379    0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0832    5.6977    0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    4.3110   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775    4.0614   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0366    2.6990   -1.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0817    1.5125   -0.8169 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8686    1.8298    0.3678 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8297    0.6637    0.6662 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321   -0.6925    0.8346 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3280   -0.6897    2.0233 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9729   -0.9299    3.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0058   -0.8836    4.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1680   -1.1522    3.3248 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2677   -0.9879   -0.4200 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1806   -2.4942   -0.5917 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0792   -3.3890   -0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9700   -3.1033    0.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0030   -2.6447   -1.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1205   -1.6215   -2.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -0.2008   -1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8314    0.1207   -0.6613 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8933    0.2193    0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6463    3.1707    0.1498 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7797    3.0688   -0.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648    5.4797    1.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3458    7.2031    0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3722    6.4556   -0.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1388    4.8848   -1.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9438    2.6213   -0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3577    2.6670   -2.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520    1.4227   -1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2521    1.9783    1.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5518    0.5524   -0.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4024    0.9067    1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9099   -1.4582    0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5187   -1.0751    5.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7681   -1.6545    4.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4648    0.1069    4.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9648   -0.8498   -1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6518   -3.4690    0.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8012   -4.4090   -1.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7467   -2.9993   -1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9687   -2.6849    0.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4377   -3.0054    1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1205   -4.1791    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4299   -3.6536   -1.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3342   -2.5420   -2.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8853   -1.7714   -1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6196   -1.7742   -3.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8854   -0.0609   -2.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    0.4991   -2.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7815    0.7667    0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5277    0.7406    1.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2603   -0.7485    0.7916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1038    3.4032    1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2411    4.0424   -1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5841    2.4179   -0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4237    2.6804   -1.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 22  1  1
  3 23  1  0
  4  3  2  0
 19 18  1  0
 19 20  1  0
 21  6  1  0
 14  9  1  0
  3  2  1  0
  2  1  2  3
  9  8  1  0
 15 16  1  6
  8  7  1  0
  9 10  1  0
 18 15  1  0
  7 32  1  1
 15 14  1  0
 23 24  1  0
  6  7  1  0
 15 17  1  0
  7 23  1  0
  6 31  1  6
 21 20  1  0
 14 39  1  6
  4  5  1  0
 10 11  1  0
  5  6  1  0
 11 13  2  0
 21 14  1  0
 11 12  1  0
  9 35  1  1
 19 48  1  0
 19 49  1  0
 18 46  1  0
 18 47  1  0
 20 50  1  0
 20 51  1  0
  8 33  1  0
  8 34  1  0
  5 29  1  0
  5 30  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  1
  4 28  1  0
  2 27  1  0
  1 25  1  0
  1 26  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 12 36  1  0
 12 37  1  0
 12 38  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       2.190   6.138   0.643  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.083   5.698   0.031  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.714   4.311  -0.237  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.478   4.061  -0.808  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.037   2.699  -1.086  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.082   1.513  -0.817  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.869   1.830   0.368  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.830   0.664   0.666  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.132  -0.693   0.835  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.328  -0.690   2.023  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.973  -0.930   3.197  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.006  -0.884   4.330  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.168  -1.152   3.325  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.268  -0.988  -0.420  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.181  -2.494  -0.592  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.079  -3.389  -0.760  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.970  -3.103   0.582  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.003  -2.645  -1.897  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.120  -1.621  -2.042  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.571  -0.201  -1.989  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.831   0.121  -0.661  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.893   0.219   0.463  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.646   3.171   0.150  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.780   3.069  -0.887  0.00  0.00           C+0
HETATM   25  H   UNK     0       2.965   5.480   1.018  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.346   7.203   0.786  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.372   6.456  -0.299  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.139   4.885  -1.073  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.944   2.621  -0.480  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.358   2.667  -2.134  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.552   1.423  -1.712  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.252   1.978   1.265  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.552   0.552  -0.150  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.402   0.907   1.569  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.910  -1.458   0.925  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.519  -1.075   5.271  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.768  -1.655   4.192  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.465   0.107   4.382  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.965  -0.850  -1.265  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.652  -3.469   0.169  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.801  -4.409  -1.052  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.747  -2.999  -1.537  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.969  -2.685   0.697  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.438  -3.005   1.531  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.121  -4.179   0.424  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.430  -3.654  -1.965  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.334  -2.542  -2.763  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.885  -1.771  -1.274  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.620  -1.774  -3.007  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.885  -0.061  -2.836  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.400   0.499  -2.151  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.781   0.767   0.128  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.528   0.741   1.351  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.260  -0.749   0.792  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.104   3.403   1.121  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.241   4.042  -1.084  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.584   2.418  -0.531  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.424   2.680  -1.846  0.00  0.00           H+0
CONECT    1    2   25   26                                                  
CONECT    2    3    1   27                                                  
CONECT    3   23    4    2                                                  
CONECT    4    3    5   28                                                  
CONECT    5    4    6   29   30                                             
CONECT    6   21    7   31    5                                             
CONECT    7    8   32    6   23                                             
CONECT    8    9    7   33   34                                             
CONECT    9   14    8   10   35                                             
CONECT   10    9   11                                                       
CONECT   11   10   13   12                                                  
CONECT   12   11   36   37   38                                             
CONECT   13   11                                                            
CONECT   14    9   15   39   21                                             
CONECT   15   16   18   14   17                                             
CONECT   16   15   40   41   42                                             
CONECT   17   15   43   44   45                                             
CONECT   18   19   15   46   47                                             
CONECT   19   18   20   48   49                                             
CONECT   20   19   21   50   51                                             
CONECT   21   22    6   20   14                                             
CONECT   22   21   52   53   54                                             
CONECT   23    3   24    7   55                                             
CONECT   24   23   56   57   58                                             
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    2                                                            
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    5                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34    8                                                            
CONECT   35    9                                                            
CONECT   36   12                                                            
CONECT   37   12                                                            
CONECT   38   12                                                            
CONECT   39   14                                                            
CONECT   40   16                                                            
CONECT   41   16                                                            
CONECT   42   16                                                            
CONECT   43   17                                                            
CONECT   44   17                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   22                                                            
CONECT   53   22                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   24                                                            
CONECT   58   24                                                            
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
    2.1899    6.1379    0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0832    5.6977    0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    4.3110   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775    4.0614   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0366    2.6990   -1.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0817    1.5125   -0.8169 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8686    1.8298    0.3678 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8297    0.6637    0.6662 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321   -0.6925    0.8346 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3280   -0.6897    2.0233 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9729   -0.9299    3.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0058   -0.8836    4.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1680   -1.1522    3.3248 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2677   -0.9879   -0.4200 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1806   -2.4942   -0.5917 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0792   -3.3890   -0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9700   -3.1033    0.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0030   -2.6447   -1.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1205   -1.6215   -2.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -0.2008   -1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8314    0.1207   -0.6613 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8933    0.2193    0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6463    3.1707    0.1498 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7797    3.0688   -0.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648    5.4797    1.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3458    7.2031    0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3722    6.4556   -0.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1388    4.8848   -1.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9438    2.6213   -0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3577    2.6670   -2.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520    1.4227   -1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2521    1.9783    1.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5518    0.5524   -0.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4024    0.9067    1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9099   -1.4582    0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5187   -1.0751    5.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7681   -1.6545    4.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4648    0.1069    4.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9648   -0.8498   -1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6518   -3.4690    0.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8012   -4.4090   -1.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7467   -2.9993   -1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9687   -2.6849    0.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4377   -3.0054    1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1205   -4.1791    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4299   -3.6536   -1.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3342   -2.5420   -2.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8853   -1.7714   -1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6196   -1.7742   -3.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8854   -0.0609   -2.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    0.4991   -2.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7815    0.7667    0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5277    0.7406    1.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2603   -0.7485    0.7916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1038    3.4032    1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2411    4.0424   -1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5841    2.4179   -0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4237    2.6804   -1.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 22  1  1
  3 23  1  0
  4  3  2  0
 19 18  1  0
 19 20  1  0
 21  6  1  0
 14  9  1  0
  3  2  1  0
  2  1  2  3
  9  8  1  0
 15 16  1  6
  8  7  1  0
  9 10  1  0
 18 15  1  0
  7 32  1  1
 15 14  1  0
 23 24  1  0
  6  7  1  0
 15 17  1  0
  7 23  1  0
  6 31  1  6
 21 20  1  0
 14 39  1  6
  4  5  1  0
 10 11  1  0
  5  6  1  0
 11 13  2  0
 21 14  1  0
 11 12  1  0
  9 35  1  1
 19 48  1  0
 19 49  1  0
 18 46  1  0
 18 47  1  0
 20 50  1  0
 20 51  1  0
  8 33  1  0
  8 34  1  0
  5 29  1  0
  5 30  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  1
  4 28  1  0
  2 27  1  0
  1 25  1  0
  1 26  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 12 36  1  0
 12 37  1  0
 12 38  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(5S,8S,10R,14R)-6b-Acetoxycassa-12,15-diene	Generator
(5S,8S,10R,14R)-6Β-acetoxycassa-12,15-diene	Generator

Chemical Formula

C₂₂H₃₄O₂

Average Mass

330.5120 Da

Monoisotopic Mass

330.25588 Da

IUPAC Name

(1R,4aS,4bR,8aS,9R,10aS)-2-ethenyl-1,4b,8,8-tetramethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-9-yl acetate

Traditional Name

(1R,4aS,4bR,8aS,9R,10aS)-2-ethenyl-1,4b,8,8-tetramethyl-1,4,4a,5,6,7,8a,9,10,10a-decahydrophenanthren-9-yl acetate

CAS Registry Number

Not Available

SMILES

[H]C([H])=C([H])C1=C([H])C([H])([H])[C@@]2([H])[C@@]([H])(C([H])([H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]3([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]23C([H])([H])[H])[C@@]1([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H34O2/c1-7-16-9-10-18-17(14(16)2)13-19(24-15(3)23)20-21(4,5)11-8-12-22(18,20)6/h7,9,14,17-20H,1,8,10-13H2,2-6H3/t14-,17-,18-,19+,20-,22+/m0/s1

InChI Key

HYHIOWBLMCOLTB-QBUJOIIVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Coulteria platyloba	JEOL database	Gomez-Hurtado, M. A., et. al, Phytochem. 96, 397 (2013)

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
Carboxylic acid ester
Monocarboxylic acid or derivatives
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	5.36	ALOGPS
logP	4.99	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.44 m³·mol⁻¹	ChemAxon
Polarizability	39.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

102497675

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gomez-Hurtado, M. A., et al. (2013). Gomez-Hurtado, M. A., et. al, Phytochem. 96, 397 (2013). Phytochem..

Showing NP-Card for (-)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene (NP0042721)

MOL for NP0042721 ((-)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene)

3D MOL for NP0042721 ((-)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene)

3D SDF for NP0042721 ((-)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene)

3D-SDF for NP0042721 ((-)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene)

PDB for NP0042721 ((-)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene)

3D PDB for NP0042721 ((-)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene)

SMILES for NP0042721 ((-)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene)

INCHI for NP0042721 ((-)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene)

Structure for NP0042721 ((-)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene)

3D Structure for NP0042721 ((-)-(5S,6R,8S,9S,10R,12Z,14R)-6-acetoxycassa-12,15-diene)