NP-MRD: Showing NP-Card for (1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one (NP0231921)

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Record Information

Version

2.0

Created at

2022-09-06 12:58:25 UTC

Updated at

2022-09-06 12:58:25 UTC

NP-MRD ID

NP0231921

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one

Description

Stigmasta-3,5-dien-7-one belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. (1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one is found in Harrisonia abyssinica and Populus tremuloides. (1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one was first documented in 2012 (PMID: 23157739). Stigmasta-3,5-dien-7-one is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 25058466) (PMID: 28587079) (PMID: 23148482) (PMID: 26707503) (PMID: 22490120).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272006262D          

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M  END

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  Mrv1652309272006262D          

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 10 18  1  0  0  0  0
 18 11  1  0  0  0  0
  1 14  2  0  0  0  0
 17 12  1  0  0  0  0
 12  4  1  6  0  0  0
 15  6  1  1  0  0  0
 12 11  1  0  0  0  0
 11  3  1  1  0  0  0
 18 13  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 34  1  6  0  0  0
 24 25  1  0  0  0  0
 24 33  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 31  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 31 32  1  0  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
 20  5  1  6  0  0  0
 15 20  1  0  0  0  0
 16 19  1  0  0  0  0
 19  2  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0231921

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])C(=O)C=C4C=CCC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O/c1-7-21(19(2)3)12-11-20(4)23-13-14-24-27-25(15-17-29(23,24)6)28(5)16-9-8-10-22(28)18-26(27)30/h8,10,18-21,23-25,27H,7,9,11-17H2,1-6H3/t20-,21-,23-,24+,25+,27+,28+,29-/m1/s1

> <INCHI_KEY>
LCFUUGFUQQAYMY-CJAQKTMASA-N

> <FORMULA>
C29H46O

> <MOLECULAR_WEIGHT>
410.686

> <EXACT_MASS>
410.354866101

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
52.76608538753429

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-5,7-dien-9-one

> <ALOGPS_LOGP>
7.36

> <JCHEM_LOGP>
8.305768265333334

> <ALOGPS_LOGS>
-7.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.853176098666231

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
129.85719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-5,7-dien-9-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8666.0258661.671   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8666.0218667.865   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8662.0258665.538   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0    8663.3568663.231   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8666.0218663.231   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8664.6908665.538   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8660.6948664.759   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.3608663.989   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8659.3608662.449   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8660.6948661.679   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.0288663.989   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.3578664.761   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8663.3578661.681   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.6918662.451   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.6918663.991   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.6898667.089   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.3558666.319   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8662.0288662.449   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.0238666.319   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.0238664.779   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8667.4878664.303   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.3928665.549   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.4878666.795   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8667.4878668.335   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.8198669.105   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8670.1558668.335   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8671.4888669.105   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8671.4888670.645   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8672.8208671.415   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8670.1558671.415   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8672.8208668.335   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8674.1568669.105   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8666.1528669.105   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0    8668.8198667.565   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2   19                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5   20                                                            
CONECT    6   15                                                            
CONECT    7    8   11                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   18                                                       
CONECT   11    7   18   12    3                                             
CONECT   12   15   17    4   11                                             
CONECT   13   14   18                                                       
CONECT   14   13   15    1                                                  
CONECT   15   12   14    6   20                                             
CONECT   16   17   19                                                       
CONECT   17   16   12                                                       
CONECT   18   10   11   13                                                  
CONECT   19   20   23   16    2                                             
CONECT   20   19   21    5   15                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   24   34   19   22                                             
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27   32                                                       
CONECT   32   31                                                            
CONECT   33   24                                                            
CONECT   34   23                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Stigma-3,5-dien-7-one	PhytoBank
Stigmasta-3,5-dien-7-one	PhytoBank
delta3,5-stigmastadien-7-one	PhytoBank
Δ3,5-stigmastadien-7-one	PhytoBank
(24R)-Stigmast-3,5-dien-7-one	PhytoBank
(24R)-Stigmasta-3,5-dien-7-one	PhytoBank
7-keto-beta-Sitosta-3,5-diene	PhytoBank
7-keto-β-Sitosta-3,5-diene	PhytoBank
Tremulone	PhytoBank

Chemical Formula

C₂₉H₄₆O

Average Mass

410.6860 Da

Monoisotopic Mass

410.35487 Da

IUPAC Name

(1S,2R,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-5,7-dien-9-one

Traditional Name

(1S,2R,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-5,7-dien-9-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])C(=O)C=C4C=CCC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C

InChI Identifier

InChI=1S/C29H46O/c1-7-21(19(2)3)12-11-20(4)23-13-14-24-27-25(15-17-29(23,24)6)28(5)16-9-8-10-22(28)18-26(27)30/h8,10,18-21,23-25,27H,7,9,11-17H2,1-6H3/t20-,21-,23-,24+,25+,27+,28+,29-/m1/s1

InChI Key

LCFUUGFUQQAYMY-CJAQKTMASA-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
Harrisonia abyssinica	LOTUS Database	35616633
Populus tremuloides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

Triterpenoid
Stigmastane-skeleton
7-oxosteroid
Oxosteroid
Cyclohexenone
Ketone
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	7.36	ALOGPS
logP	8.31	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	129.86 m³·mol⁻¹	ChemAxon
Polarizability	52.77 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

20037917

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12444466

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pensec F, Paczkowski C, Grabarczyk M, Wozniak A, Benard-Gellon M, Bertsch C, Chong J, Szakiel A: Changes in the triterpenoid content of cuticular waxes during fruit ripening of eight grape (Vitis vinifera) cultivars grown in the Upper Rhine Valley. J Agric Food Chem. 2014 Aug 13;62(32):7998-8007. doi: 10.1021/jf502033s. Epub 2014 Jul 30. [PubMed:25058466 ]
Gutierrez Nava ZJ, Jimenez-Aparicio AR, Herrera-Ruiz ML, Jimenez-Ferrer E: Immunomodulatory Effect of Agave tequilana Evaluated on an Autoimmunity Like-SLE Model Induced in Balb/c Mice with Pristane. Molecules. 2017 May 25;22(6):848. doi: 10.3390/molecules22060848. [PubMed:28587079 ]
Szakiel A, Nizynski B, Paczkowski C: Triterpenoid profile of flower and leaf cuticular waxes of heather Calluna vulgaris. Nat Prod Res. 2013 Aug;27(15):1404-7. doi: 10.1080/14786419.2012.742083. Epub 2012 Nov 13. [PubMed:23148482 ]
Park SJ, Kim YW, Park MK, Byun SH, Kim SC, Lee JR: Anti-inflammatory Steroid from Phragmitis rhizoma Modulates LPS-Mediated Signaling Through Inhibition of NF-kappaB Pathway. Inflammation. 2016 Apr;39(2):727-34. doi: 10.1007/s10753-015-0299-6. [PubMed:26707503 ]
Szakiel A, Paczkowski C, Huttunen S: Triterpenoid content of berries and leaves of bilberry Vaccinium myrtillus from Finland and Poland. J Agric Food Chem. 2012 Dec 5;60(48):11839-49. doi: 10.1021/jf3046895. Epub 2012 Nov 27. [PubMed:23157739 ]
Szakiel A, Paczkowski C, Koivuniemi H, Huttunen S: Comparison of the triterpenoid content of berries and leaves of lingonberry Vaccinium vitis-idaea from Finland and Poland. J Agric Food Chem. 2012 May 16;60(19):4994-5002. doi: 10.1021/jf300375b. Epub 2012 May 7. [PubMed:22490120 ]
LOTUS database [Link]

Showing NP-Card for (1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one (NP0231921)

MOL for NP0231921 ((1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

3D MOL for NP0231921 ((1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

3D SDF for NP0231921 ((1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

3D-SDF for NP0231921 ((1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

PDB for NP0231921 ((1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

3D PDB for NP0231921 ((1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

SMILES for NP0231921 ((1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

INCHI for NP0231921 ((1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

Structure for NP0231921 ((1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

3D Structure for NP0231921 ((1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)