NP-MRD: Showing NP-Card for (1r,3ar,5ar,6s,7s,9ar,9br,11ar)-7-hydroxy-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carbaldehyde (NP0279715)

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Record Information

Version

2.0

Created at

2022-09-09 05:12:28 UTC

Updated at

2022-09-09 05:12:29 UTC

NP-MRD ID

NP0279715

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3ar,5ar,6s,7s,9ar,9br,11ar)-7-hydroxy-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carbaldehyde

Description

3Beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde is considered to be a sterol lipid molecule. (1r,3ar,5ar,6s,7s,9ar,9br,11ar)-7-hydroxy-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carbaldehyde is found in Apis cerana. 3Beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

ChEBI
  Mrv0541 02241222392D          

 35 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END

ChEBI
  Mrv0541 02241222392D          

 35 38  0  0  1  0            999 V2000
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   16.3624   -8.6716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.6479   -9.0841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5750   -9.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0768   -9.0841    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.5785   -9.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7816  -10.1622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  2  1  1  0  0  0  0
 30  2  1  0  0  0  0
 30 33  1  0  0  0  0
 28 33  1  0  0  0  0
  3  4  1  0  0  0  0
 28  3  1  0  0  0  0
 13  4  2  0  0  0  0
 11  5  1  0  0  0  0
  5 28  1  0  0  0  0
  5 10  1  1  0  0  0
 11  6  1  0  0  0  0
  6  7  1  0  0  0  0
 15  7  1  0  0  0  0
 14  8  1  0  0  0  0
  9  8  1  0  0  0  0
  9 26  1  0  0  0  0
 13 11  1  0  0  0  0
 11 12  1  6  0  0  0
 14 13  1  0  0  0  0
 14 15  1  0  0  0  0
 14 17  1  6  0  0  0
 15 26  1  0  0  0  0
 15 16  1  1  0  0  0
 18 19  1  0  0  0  0
 18 25  1  0  0  0  0
 19 24  1  0  0  0  0
 20 25  1  0  0  0  0
 22 20  1  0  0  0  0
 20 21  1  0  0  0  0
 24 23  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 28 29  1  6  0  0  0
 30 31  1  1  0  0  0
 33 32  1  1  0  0  0
 33 34  1  6  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0279715

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])[C@](C)(C=O)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O2/c1-19(2)8-7-9-20(3)22-11-12-23-21-10-13-25-28(5,24(21)14-16-27(22,23)4)17-15-26(31)29(25,6)18-30/h10,18-20,22-26,31H,7-9,11-17H2,1-6H3/t20-,22-,23+,24+,25-,26+,27-,28-,29+/m1/s1

> <INCHI_KEY>
HCOOTBJPHHNRCV-AQTSNUJDSA-N

> <FORMULA>
C29H48O2

> <MOLECULAR_WEIGHT>
428.6902

> <EXACT_MASS>
428.36543078

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
54.51400941893073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,6S,7R,11R,14R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-ene-6-carbaldehyde

> <ALOGPS_LOGP>
7.02

> <JCHEM_LOGP>
6.888939053666668

> <ALOGPS_LOGS>
-6.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.54217663732149

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9990519388355805

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
130.27799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.23e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,6S,7R,11R,14R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-ene-6-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      31.877 -13.877   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.543 -14.647   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      34.544 -16.957   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      35.878 -16.187   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.210 -14.647   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      34.544 -12.337   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      35.878 -11.567   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      38.676 -14.353   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      39.581 -13.107   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.210 -13.107   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.544 -13.877   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0      34.544 -15.417   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0      35.878 -14.647   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.211 -13.877   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.211 -12.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.211 -10.797   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      37.211 -15.417   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0      41.343 -10.321   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      40.010  -9.551   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      44.011 -10.321   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      44.011 -11.861   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      45.345  -9.551   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      37.342  -9.551   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      38.676 -10.321   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      42.677  -9.551   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      38.676 -11.861   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      40.010 -11.091   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0      33.210 -16.187   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      33.210 -17.727   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0      30.543 -16.187   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      29.209 -16.957   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      32.807 -18.651   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      31.877 -16.957   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      30.947 -18.571   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      29.459 -18.969   0.000  0.00  0.00           O+0
CONECT    1    5    2                                                       
CONECT    2    1   30                                                       
CONECT    3    4   28                                                       
CONECT    4    3   13                                                       
CONECT    5    1   11   28   10                                             
CONECT    6   11    7                                                       
CONECT    7    6   15                                                       
CONECT    8   14    9                                                       
CONECT    9    8   26                                                       
CONECT   10    5                                                            
CONECT   11    5    6   13   12                                             
CONECT   12   11                                                            
CONECT   13    4   11   14                                                  
CONECT   14    8   13   15   17                                             
CONECT   15    7   14   26   16                                             
CONECT   16   15                                                            
CONECT   17   14                                                            
CONECT   18   19   25                                                       
CONECT   19   18   24                                                       
CONECT   20   25   22   21                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   24                                                            
CONECT   24   19   23   26                                                  
CONECT   25   18   20                                                       
CONECT   26    9   15   24   27                                             
CONECT   27   26                                                            
CONECT   28   33    3    5   29                                             
CONECT   29   28                                                            
CONECT   30    2   33   31                                                  
CONECT   31   30                                                            
CONECT   32   33                                                            
CONECT   33   30   28   32   34                                             
CONECT   34   33   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
3b-Hydroxy-4b-methyl-5a-cholest-7-ene-4a-carbaldehyde	Generator
3Β-hydroxy-4β-methyl-5α-cholest-7-ene-4α-carbaldehyde	Generator

Chemical Formula

C₂₉H₄₈O₂

Average Mass

428.6902 Da

Monoisotopic Mass

428.36543 Da

IUPAC Name

(1R,2R,5S,6S,7R,11R,14R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-ene-6-carbaldehyde

Traditional Name

(1R,2R,5S,6S,7R,11R,14R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-ene-6-carbaldehyde

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])[C@](C)(C=O)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C29H48O2/c1-19(2)8-7-9-20(3)22-11-12-23-21-10-13-25-28(5,24(21)14-16-27(22,23)4)17-15-26(31)29(25,6)18-30/h10,18-20,22-26,31H,7-9,11-17H2,1-6H3/t20-,22-,23+,24+,25-,26+,27-,28-,29+/m1/s1

InChI Key

HCOOTBJPHHNRCV-AQTSNUJDSA-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
Apis cerana	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
Cholesterol-skeleton
Diterpenoid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
3-beta-hydroxysteroid
Hydroxysteroid
Delta-7-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Aldehyde
Alcohol
Organic oxide
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-sterol (CHEBI:16286 )
Cholesterol and derivatives (LMST01010204 )

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	7.02	ALOGPS
logP	6.89	ChemAxon
logS	-6.7	ALOGPS
pKa (Strongest Acidic)	14.54	ChemAxon
pKa (Strongest Basic)	-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	6	ChemAxon
Refractivity	130.28 m³·mol⁻¹	ChemAxon
Polarizability	54.51 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	Yes	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

21145202

PDB ID

Not Available

ChEBI ID

16286

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3ar,5ar,6s,7s,9ar,9br,11ar)-7-hydroxy-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carbaldehyde (NP0279715)

MOL for NP0279715 ((1r,3ar,5ar,6s,7s,9ar,9br,11ar)-7-hydroxy-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carbaldehyde)

3D MOL for NP0279715 ((1r,3ar,5ar,6s,7s,9ar,9br,11ar)-7-hydroxy-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carbaldehyde)

3D SDF for NP0279715 ((1r,3ar,5ar,6s,7s,9ar,9br,11ar)-7-hydroxy-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carbaldehyde)

3D-SDF for NP0279715 ((1r,3ar,5ar,6s,7s,9ar,9br,11ar)-7-hydroxy-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carbaldehyde)

PDB for NP0279715 ((1r,3ar,5ar,6s,7s,9ar,9br,11ar)-7-hydroxy-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carbaldehyde)

3D PDB for NP0279715 ((1r,3ar,5ar,6s,7s,9ar,9br,11ar)-7-hydroxy-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carbaldehyde)

SMILES for NP0279715 ((1r,3ar,5ar,6s,7s,9ar,9br,11ar)-7-hydroxy-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carbaldehyde)

INCHI for NP0279715 ((1r,3ar,5ar,6s,7s,9ar,9br,11ar)-7-hydroxy-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carbaldehyde)

Structure for NP0279715 ((1r,3ar,5ar,6s,7s,9ar,9br,11ar)-7-hydroxy-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carbaldehyde)

3D Structure for NP0279715 ((1r,3ar,5ar,6s,7s,9ar,9br,11ar)-7-hydroxy-6,9a,11a-trimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carbaldehyde)