NP-MRD: Showing NP-Card for (3r)-1-[(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one (NP0147296)

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Record Information

Version

2.0

Created at

2022-09-02 02:52:09 UTC

Updated at

2022-09-02 02:52:10 UTC

NP-MRD ID

NP0147296

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-1-[(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one

Description

(3R)-1-[(1S,2R,7S,10S,11S,14S,15S)-14-[(1S)-1-(dimethylamino)ethyl]-2,15-dimethyl-6-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-4-en-5-yl]-3-(propan-2-yl)azetidin-2-one belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. (3r)-1-[(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one is found in Pachysandra procumbens. Based on a literature review very few articles have been published on (3R)-1-[(1S,2R,7S,10S,11S,14S,15S)-14-[(1S)-1-(dimethylamino)ethyl]-2,15-dimethyl-6-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-4-en-5-yl]-3-(propan-2-yl)azetidin-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022204522D          

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M  END

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M  END


  Mrv1652309022204522D          

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    4.4821   -1.1154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973    0.7268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5567   -1.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4115   -1.8183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 19 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 15 29  1  0  0  0  0
 10 29  1  0  0  0  0
 12 30  1  0  0  0  0
  7 30  1  0  0  0  0
 30 31  2  0  0  0  0
  6 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0147296

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1CN(C1=O)C1=CC[C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@@H]3CC[C@@H]2C1=O)[C@H](C)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H46N2O2/c1-17(2)20-16-31(27(20)33)25-13-15-29(5)23-12-14-28(4)21(18(3)30(6)7)10-11-22(28)19(23)8-9-24(29)26(25)32/h13,17-24H,8-12,14-16H2,1-7H3/t18-,19-,20-,21+,22-,23-,24+,28+,29+/m0/s1

> <INCHI_KEY>
IVYPSBIZZDNZBC-JAYKOCSJSA-N

> <FORMULA>
C29H46N2O2

> <MOLECULAR_WEIGHT>
454.699

> <EXACT_MASS>
454.355928729

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.654681258626866

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-1-[(1S,2R,7S,10S,11S,14S,15S)-14-[(1S)-1-(dimethylamino)ethyl]-2,15-dimethyl-6-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-4-en-5-yl]-3-(propan-2-yl)azetidin-2-one

> <ALOGPS_LOGP>
5.51

> <JCHEM_LOGP>
5.0490750150000006

> <ALOGPS_LOGS>
-5.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.600296987951964

> <JCHEM_POLAR_SURFACE_AREA>
40.620000000000005

> <JCHEM_REFRACTIVITY>
135.58249999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-1-[(1S,2R,7S,10S,11S,14S,15S)-14-[(1S)-1-(dimethylamino)ethyl]-2,15-dimethyl-6-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-4-en-5-yl]-3-isopropylazetidin-2-one

> <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      -2.350  -1.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.357  -0.343   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.880   1.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.159  -0.615   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.423   0.266   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.303  -0.998   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.374  -3.259   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.366  -1.095   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.883  -3.790   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.408  -3.579   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      13.303  -5.217   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      14.248  -6.432   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.777  -5.427   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.070  -4.010   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.367  -2.082   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.288   1.357   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.039  -1.878   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.768  -3.394   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8   30                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   29                                             
CONECT   11   10                                                            
CONECT   12   10   13   30                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   29                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   19   16   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   15   10                                                  
CONECT   30   12    7   31                                                  
CONECT   31   30                                                            
CONECT   32    6    4   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₆N₂O₂

Average Mass

454.6990 Da

Monoisotopic Mass

454.35593 Da

IUPAC Name

(3R)-1-[(1S,2R,7S,10S,11S,14S,15S)-14-[(1S)-1-(dimethylamino)ethyl]-2,15-dimethyl-6-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-4-en-5-yl]-3-(propan-2-yl)azetidin-2-one

Traditional Name

(3R)-1-[(1S,2R,7S,10S,11S,14S,15S)-14-[(1S)-1-(dimethylamino)ethyl]-2,15-dimethyl-6-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-4-en-5-yl]-3-isopropylazetidin-2-one

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1CN(C1=O)C1=CC[C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@@H]3CC[C@@H]2C1=O)[C@H](C)N(C)C

InChI Identifier

InChI=1S/C29H46N2O2/c1-17(2)20-16-31(27(20)33)25-13-15-29(5)23-12-14-28(4)21(18(3)30(6)7)10-11-22(28)19(23)8-9-24(29)26(25)32/h13,17-24H,8-12,14-16H2,1-7H3/t18-,19-,20-,21+,22-,23-,24+,28+,29+/m0/s1

InChI Key

IVYPSBIZZDNZBC-JAYKOCSJSA-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
Pachysandra procumbens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

22-azasteroid
Pregnane-skeleton
Pregnane-type alkaloid
Steroidal alkaloid
Oxosteroid
4-oxosteroid
Azasteroid
Monobactam
Alkaloid or derivatives
Cyclohexenone
Beta-lactam
Tertiary carboxylic acid amide
Amino acid or derivatives
Azetidine
Carboxamide group
Ketone
Lactam
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxide
Amine
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	5.51	ALOGPS
logP	5.05	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	9.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.62 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	135.58 m³·mol⁻¹	ChemAxon
Polarizability	55.65 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

163017016

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r)-1-[(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one (NP0147296)

MOL for NP0147296 ((3r)-1-[(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

3D MOL for NP0147296 ((3r)-1-[(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

3D SDF for NP0147296 ((3r)-1-[(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

3D-SDF for NP0147296 ((3r)-1-[(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

PDB for NP0147296 ((3r)-1-[(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

3D PDB for NP0147296 ((3r)-1-[(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

SMILES for NP0147296 ((3r)-1-[(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

INCHI for NP0147296 ((3r)-1-[(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

Structure for NP0147296 ((3r)-1-[(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)

3D Structure for NP0147296 ((3r)-1-[(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-3-isopropylazetidin-2-one)