NP-MRD: Showing NP-Card for [(1s,2r,4as,4br,7r,8ar)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2h-phenanthren-1-yl]methyl acetate (NP0157588)

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Record Information

Version

2.0

Created at

2022-09-02 15:00:17 UTC

Updated at

2022-09-02 15:00:17 UTC

NP-MRD ID

NP0157588

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,2r,4as,4br,7r,8ar)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2h-phenanthren-1-yl]methyl acetate

Description

(1S)-7beta-Ethenyl-1,2,3,4,4aalpha,4b,5,6,7,8,8aalpha,9-dodecahydro-2alpha-hydroxy-1,4bbeta,7-trimethyl-1beta-phenanthrenemethanol alpha-acetate belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred. [(1s,2r,4as,4br,7r,8ar)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2h-phenanthren-1-yl]methyl acetate is found in Trichogonia villosa. Based on a literature review very few articles have been published on (1S)-7beta-Ethenyl-1,2,3,4,4aalpha,4b,5,6,7,8,8aalpha,9-dodecahydro-2alpha-hydroxy-1,4bbeta,7-trimethyl-1beta-phenanthrenemethanol alpha-acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217002D          

 25 27  0  0  1  0            999 V2000
   -0.5993   -0.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425   -1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7425   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3772   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4587   -3.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0907   -4.1197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474   -4.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5794   -5.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1722   -5.2144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 14 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  6  0  0  0
  7 24  1  0  0  0  0
 24 25  1  0  0  0  0
  3 25  1  0  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
    5.8211    0.1310    1.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4295   -0.0816    0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0634    0.2254   -0.3959 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2632    0.7306   -1.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3445    1.2894    0.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3076    0.8162    1.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3020   -0.1492    0.7339 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1768   -1.2848    1.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0662    0.4511    0.5901 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8770    0.4286    1.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0715    1.3154    1.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5661    1.5143    0.3053 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1444    2.7433   -0.2455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2674    0.3678   -0.6440 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5061    0.9019   -2.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3178   -0.6917   -0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6219   -0.1608   -0.4983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7580   -0.9332   -0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1179   -0.3463   -0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5961   -2.1520   -0.0546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8941   -0.1451   -0.4728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4463   -1.0965   -1.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9143   -1.6893   -1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8206   -0.6347   -0.5822 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2620   -1.0553   -0.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8314   -0.1199    1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1149    0.5553    2.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1411   -0.5169   -0.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    1.3525   -1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3559   -0.1240   -2.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3404    1.2791   -2.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8807    2.0345   -0.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0841    1.8869    0.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7365    0.4746    2.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7134    1.7356    1.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796   -1.9091    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1330   -0.7612    2.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3113   -1.9192    1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1007    1.5403    0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3235    0.7591    2.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2535   -0.6264    1.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7949    2.3341    2.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9029    0.9854    2.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6872    1.5888    0.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7117    3.4933    0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4442    0.1026   -2.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5568    1.2702   -2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8536    1.7690   -2.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1587   -1.1090    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2323   -1.5313   -1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0061    0.7427   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6551   -0.8472   -1.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6341   -0.4777    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252   -1.4908   -2.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2929   -2.0340   -2.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8641   -2.5661   -0.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7694    0.2389   -1.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4889   -1.7863    0.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4764   -1.5805   -1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 20  2  0
 18 17  1  0
 17 16  1  0
 14 16  1  1
 14 15  1  0
 14 12  1  0
 12 13  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  3  2  1  1
  2  1  2  3
 21 14  1  0
  7 24  1  0
  7  9  1  0
 19 51  1  0
 19 52  1  0
 19 53  1  0
 16 49  1  0
 16 50  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 12 44  1  1
 13 45  1  0
 11 42  1  0
 11 43  1  0
 10 40  1  0
 10 41  1  0
  9 39  1  6
 22 54  1  0
 23 55  1  0
 23 56  1  0
 24 57  1  6
 25 58  1  0
 25 59  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
  2 28  1  0
  1 26  1  0
  1 27  1  0
M  END


  Mrv1652309022217002D          

 25 27  0  0  1  0            999 V2000
   -0.5993   -0.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425   -1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7425   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3772   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4587   -3.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0907   -4.1197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474   -4.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5794   -5.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1722   -5.2144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 14 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  6  0  0  0
  7 24  1  0  0  0  0
 24 25  1  0  0  0  0
  3 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157588

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@@]1(C)[C@H](O)CC[C@@H]2C1=CC[C@@H]1C[C@@](C)(CC[C@@]21C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O3/c1-6-20(3)11-12-21(4)16(13-20)7-8-18-17(21)9-10-19(24)22(18,5)14-25-15(2)23/h6,8,16-17,19,24H,1,7,9-14H2,2-5H3/t16-,17-,19-,20-,21-,22-/m1/s1

> <INCHI_KEY>
DSZVNQDYLCQZTF-FLCGDVNSSA-N

> <FORMULA>
C22H34O3

> <MOLECULAR_WEIGHT>
346.511

> <EXACT_MASS>
346.250794955

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
41.33668749071131

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,2R,4aS,4bR,7R,8aR)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-1,2,3,4,4a,4b,5,6,7,8,8a,9-dodecahydrophenanthren-1-yl]methyl acetate

> <ALOGPS_LOGP>
5.12

> <JCHEM_LOGP>
3.805035166666668

> <ALOGPS_LOGS>
-5.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.576526540781678

> <JCHEM_PKA_STRONGEST_BASIC>
-2.984027291062093

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
101.0593

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,4aS,4bR,7R,8aR)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2H-phenanthren-1-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.119  -1.344   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.386  -2.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.386  -4.840   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644  -2.516   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.034  -3.850   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.171  -5.710   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.456  -6.700   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.636  -7.690   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.369  -9.207   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.548 -10.197   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.921  -9.733   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   25                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   24                                             
CONECT    8    7                                                            
CONECT    9    7   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   21                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   14    9   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    7   25                                                  
CONECT   25   24    3                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
(1S)-7b-Ethenyl-1,2,3,4,4aalpha,4b,5,6,7,8,8aalpha,9-dodecahydro-2a-hydroxy-1,4bbeta,7-trimethyl-1b-phenanthrenemethanol a-acetate	Generator
(1S)-7b-Ethenyl-1,2,3,4,4aalpha,4b,5,6,7,8,8aalpha,9-dodecahydro-2a-hydroxy-1,4bbeta,7-trimethyl-1b-phenanthrenemethanol a-acetic acid	Generator
(1S)-7beta-Ethenyl-1,2,3,4,4aalpha,4b,5,6,7,8,8aalpha,9-dodecahydro-2alpha-hydroxy-1,4bbeta,7-trimethyl-1beta-phenanthrenemethanol alpha-acetic acid	Generator
(1S)-7Β-ethenyl-1,2,3,4,4aalpha,4b,5,6,7,8,8aalpha,9-dodecahydro-2α-hydroxy-1,4bbeta,7-trimethyl-1β-phenanthrenemethanol α-acetate	Generator
(1S)-7Β-ethenyl-1,2,3,4,4aalpha,4b,5,6,7,8,8aalpha,9-dodecahydro-2α-hydroxy-1,4bbeta,7-trimethyl-1β-phenanthrenemethanol α-acetic acid	Generator

Chemical Formula

C₂₂H₃₄O₃

Average Mass

346.5110 Da

Monoisotopic Mass

346.25079 Da

IUPAC Name

[(1S,2R,4aS,4bR,7R,8aR)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-1,2,3,4,4a,4b,5,6,7,8,8a,9-dodecahydrophenanthren-1-yl]methyl acetate

Traditional Name

[(1S,2R,4aS,4bR,7R,8aR)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2H-phenanthren-1-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@@]1(C)[C@H](O)CC[C@@H]2C1=CC[C@@H]1C[C@@](C)(CC[C@@]21C)C=C

InChI Identifier

InChI=1S/C22H34O3/c1-6-20(3)11-12-21(4)16(13-20)7-8-18-17(21)9-10-19(24)22(18,5)14-25-15(2)23/h6,8,16-17,19,24H,1,7,9-14H2,2-5H3/t16-,17-,19-,20-,21-,22-/m1/s1

InChI Key

DSZVNQDYLCQZTF-FLCGDVNSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Trichogonia villosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Not Available

Direct Parent

Steroids and steroid derivatives

Alternative Parents

Substituents

Steroid
Sesquiterpenoid
Hydrophenanthrene
Phenanthrene
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	5.12	ALOGPS
logP	3.81	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	14.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.06 m³·mol⁻¹	ChemAxon
Polarizability	41.34 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

101320279

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,2r,4as,4br,7r,8ar)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2h-phenanthren-1-yl]methyl acetate (NP0157588)

MOL for NP0157588 ([(1s,2r,4as,4br,7r,8ar)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2h-phenanthren-1-yl]methyl acetate)

3D MOL for NP0157588 ([(1s,2r,4as,4br,7r,8ar)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2h-phenanthren-1-yl]methyl acetate)

3D SDF for NP0157588 ([(1s,2r,4as,4br,7r,8ar)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2h-phenanthren-1-yl]methyl acetate)

3D-SDF for NP0157588 ([(1s,2r,4as,4br,7r,8ar)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2h-phenanthren-1-yl]methyl acetate)

PDB for NP0157588 ([(1s,2r,4as,4br,7r,8ar)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2h-phenanthren-1-yl]methyl acetate)

3D PDB for NP0157588 ([(1s,2r,4as,4br,7r,8ar)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2h-phenanthren-1-yl]methyl acetate)

SMILES for NP0157588 ([(1s,2r,4as,4br,7r,8ar)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2h-phenanthren-1-yl]methyl acetate)

INCHI for NP0157588 ([(1s,2r,4as,4br,7r,8ar)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2h-phenanthren-1-yl]methyl acetate)

Structure for NP0157588 ([(1s,2r,4as,4br,7r,8ar)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2h-phenanthren-1-yl]methyl acetate)

3D Structure for NP0157588 ([(1s,2r,4as,4br,7r,8ar)-7-ethenyl-2-hydroxy-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2h-phenanthren-1-yl]methyl acetate)