NP-MRD: Showing NP-Card for (1r,3ar,7s,9as,11ar)-7-hydroxy-9a,11a-dimethyl-1-[(2r,3e)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one (NP0192914)

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Record Information

Version

2.0

Created at

2022-09-04 10:13:45 UTC

Updated at

2022-09-04 10:13:45 UTC

NP-MRD ID

NP0192914

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3ar,7s,9as,11ar)-7-hydroxy-9a,11a-dimethyl-1-[(2r,3e)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one

Description

3-Hydroxycholesta-5,8,22-trien-7-one, also known as 3-HCTO, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. (1r,3ar,7s,9as,11ar)-7-hydroxy-9a,11a-dimethyl-1-[(2r,3e)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one is found in Clathrina clathrus. Based on a literature review very few articles have been published on 3-Hydroxycholesta-5,8,22-trien-7-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042212132D          

 29 32  0  0  1  0            999 V2000
    8.7583   -1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6302   -2.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4347   -1.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9830   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  9 10  1  0  0  0  0
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 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
  9 17  1  0  0  0  0
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M  END

     RDKit          3D

 69 72  0  0  0  0  0  0  0  0999 V2000
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   -7.7250   -0.4458   -0.1853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6501    0.0455   -1.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3161    0.5825   -0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9758    1.7503   -1.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6910    2.2960   -1.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309042212132D          

 29 32  0  0  1  0            999 V2000
    8.7583   -1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5266    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0192914

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C\C=C\[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h6,8,16-18,20-22,28H,7,9-15H2,1-5H3/b8-6+/t18-,20+,21-,22+,26+,27-/m1/s1

> <INCHI_KEY>
AYNFEPVYJBGXLS-ODMVIQNVSA-N

> <FORMULA>
C27H40O2

> <MOLECULAR_WEIGHT>
396.615

> <EXACT_MASS>
396.302830528

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.37761271513081

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,11R,14R,15R)-5-hydroxy-2,15-dimethyl-14-[(2R,3E)-6-methylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),7-dien-9-one

> <JCHEM_LOGP>
5.994191853

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.337183328240037

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.105897308765535

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3390798286803074

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
122.98639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,11R,14R,15R)-5-hydroxy-2,15-dimethyl-14-[(2R,3E)-6-methylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),7-dien-9-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      16.349  -3.280   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.823  -3.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.243  -4.917   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.878  -2.275   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.353  -2.485   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.828   4.031   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   28                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12    9   18                                             
CONECT   18   17                                                            
CONECT   19   14   20   21   26                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   19   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   13   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
3-HCTO	MeSH

Chemical Formula

C₂₇H₄₀O₂

Average Mass

396.6150 Da

Monoisotopic Mass

396.30283 Da

IUPAC Name

(2S,5S,11R,14R,15R)-5-hydroxy-2,15-dimethyl-14-[(2R,3E)-6-methylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),7-dien-9-one

Traditional Name

(2S,5S,11R,14R,15R)-5-hydroxy-2,15-dimethyl-14-[(2R,3E)-6-methylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),7-dien-9-one

CAS Registry Number

Not Available

SMILES

CC(C)C\C=C\[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3=O

InChI Identifier

InChI=1S/C27H40O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h6,8,16-18,20-22,28H,7,9-15H2,1-5H3/b8-6+/t18-,20+,21-,22+,26+,27-/m1/s1

InChI Key

AYNFEPVYJBGXLS-ODMVIQNVSA-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
Clathrina clathrus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
7-oxosteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Oxosteroid
Hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
Organic oxide
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	5.99	ChemAxon
pKa (Strongest Acidic)	17.11	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.99 m³·mol⁻¹	ChemAxon
Polarizability	49.38 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

4943529

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6439096

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3ar,7s,9as,11ar)-7-hydroxy-9a,11a-dimethyl-1-[(2r,3e)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one (NP0192914)

MOL for NP0192914 ((1r,3ar,7s,9as,11ar)-7-hydroxy-9a,11a-dimethyl-1-[(2r,3e)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

3D MOL for NP0192914 ((1r,3ar,7s,9as,11ar)-7-hydroxy-9a,11a-dimethyl-1-[(2r,3e)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

3D SDF for NP0192914 ((1r,3ar,7s,9as,11ar)-7-hydroxy-9a,11a-dimethyl-1-[(2r,3e)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

3D-SDF for NP0192914 ((1r,3ar,7s,9as,11ar)-7-hydroxy-9a,11a-dimethyl-1-[(2r,3e)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

PDB for NP0192914 ((1r,3ar,7s,9as,11ar)-7-hydroxy-9a,11a-dimethyl-1-[(2r,3e)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

3D PDB for NP0192914 ((1r,3ar,7s,9as,11ar)-7-hydroxy-9a,11a-dimethyl-1-[(2r,3e)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

SMILES for NP0192914 ((1r,3ar,7s,9as,11ar)-7-hydroxy-9a,11a-dimethyl-1-[(2r,3e)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

INCHI for NP0192914 ((1r,3ar,7s,9as,11ar)-7-hydroxy-9a,11a-dimethyl-1-[(2r,3e)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

Structure for NP0192914 ((1r,3ar,7s,9as,11ar)-7-hydroxy-9a,11a-dimethyl-1-[(2r,3e)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

3D Structure for NP0192914 ((1r,3ar,7s,9as,11ar)-7-hydroxy-9a,11a-dimethyl-1-[(2r,3e)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)