NP-MRD: Showing NP-Card for methyl (4r)-4-[(1r,3ar,5ar,9as,11r,11ar)-11-hydroxy-3a,6,6,9a,11a-pentamethyl-3,4,7,10-tetraoxo-1h,2h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]pentanoate (NP0329235)

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Record Information

Version

2.0

Created at

2022-09-12 13:26:40 UTC

Updated at

2022-09-12 13:26:41 UTC

NP-MRD ID

NP0329235

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4r)-4-[(1r,3ar,5ar,9as,11r,11ar)-11-hydroxy-3a,6,6,9a,11a-pentamethyl-3,4,7,10-tetraoxo-1h,2h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]pentanoate

Description

Methyl (4R)-4-[(2S,7R,11R,14R,15R,16R)-16-hydroxy-2,6,6,11,15-pentamethyl-5,9,12,17-tetraoxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(10)-en-14-yl]pentanoate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review very few articles have been published on methyl (4R)-4-[(2S,7R,11R,14R,15R,16R)-16-hydroxy-2,6,6,11,15-pentamethyl-5,9,12,17-tetraoxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(10)-en-14-yl]pentanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122215262D          

 35 38  0  0  1  0            999 V2000
   -0.9747   -7.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602   -7.1030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -7.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -8.3405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1687   -7.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -7.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5977   -7.1030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5977   -6.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3121   -7.5155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3984   -8.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2053   -8.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7219   -9.0192    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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 17 19  1  0  0  0  0
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 19 21  1  0  0  0  0
  9 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  6  0  0  0
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 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
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 34 35  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309122215262D          

 35 38  0  0  1  0            999 V2000
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 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
  9 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  6  0  0  0
 16 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 15 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0329235

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O7/c1-14(8-9-20(32)35-7)15-12-19(31)28(6)21-16(29)13-17-25(2,3)18(30)10-11-26(17,4)22(21)23(33)24(34)27(15,28)5/h14-15,17,24,34H,8-13H2,1-7H3/t14-,15-,17+,24+,26+,27+,28+/m1/s1

> <INCHI_KEY>
WESQYFRWIXQVIZ-KGXWFZIOSA-N

> <FORMULA>
C28H38O7

> <MOLECULAR_WEIGHT>
486.605

> <EXACT_MASS>
486.261753564

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.42311052634824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (4R)-4-[(2S,7R,11R,14R,15R,16R)-16-hydroxy-2,6,6,11,15-pentamethyl-5,9,12,17-tetraoxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]pentanoate

> <JCHEM_LOGP>
3.6082670280000015

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.866553716588143

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.899416262896082

> <JCHEM_PKA_STRONGEST_BASIC>
-3.717589227748845

> <JCHEM_POLAR_SURFACE_AREA>
114.81

> <JCHEM_REFRACTIVITY>
128.9741

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4R)-4-[(2S,7R,11R,14R,15R,16R)-16-hydroxy-2,6,6,11,15-pentamethyl-5,9,12,17-tetraoxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]pentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.819 -14.029   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.486 -13.259   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.848 -14.029   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.848 -15.569   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.182 -13.259   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.515 -14.029   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.849 -13.259   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.849 -11.719   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.183 -14.029   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.344 -15.560   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.850 -15.881   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.476 -17.288   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.620 -14.547   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.525 -15.793   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.126 -14.227   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.602 -12.762   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.572 -11.618   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.048 -10.153   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.065 -11.938   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.035 -10.793   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.590 -13.403   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.445 -12.372   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.109 -12.442   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.078 -11.298   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.584 -10.977   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.091 -10.657   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.121 -11.802   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.628 -11.481   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.645 -13.266   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.170 -13.481   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.699 -14.805   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.139 -13.586   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.663 -15.051   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.157 -15.371   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.681 -16.836   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   21                                             
CONECT   14   13                                                            
CONECT   15   13   16   34                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    9   13   22                                             
CONECT   22   21                                                            
CONECT   23   16   24   25   32                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   23   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   15   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
Methyl (4R)-4-[(2S,7R,11R,14R,15R,16R)-16-hydroxy-2,6,6,11,15-pentamethyl-5,9,12,17-tetraoxotetracyclo[8.7.0.0,.0,]heptadec-1(10)-en-14-yl]pentanoic acid	Generator

Chemical Formula

C₂₈H₃₈O₇

Average Mass

486.6050 Da

Monoisotopic Mass

486.26175 Da

IUPAC Name

methyl (4R)-4-[(2S,7R,11R,14R,15R,16R)-16-hydroxy-2,6,6,11,15-pentamethyl-5,9,12,17-tetraoxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]pentanoate

Traditional Name

methyl (4R)-4-[(2S,7R,11R,14R,15R,16R)-16-hydroxy-2,6,6,11,15-pentamethyl-5,9,12,17-tetraoxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]pentanoate

CAS Registry Number

Not Available

SMILES

COC(=O)CC[C@@H](C)[C@H]1CC(=O)[C@@]2(C)C3=C(C(=O)[C@H](O)[C@]12C)[C@@]1(C)CCC(=O)C(C)(C)[C@@H]1CC3=O

InChI Identifier

InChI=1S/C28H38O7/c1-14(8-9-20(32)35-7)15-12-19(31)28(6)21-16(29)13-17-25(2,3)18(30)10-11-26(17,4)22(21)23(33)24(34)27(15,28)5/h14-15,17,24,34H,8-13H2,1-7H3/t14-,15-,17+,24+,26+,27+,28+/m1/s1

InChI Key

WESQYFRWIXQVIZ-KGXWFZIOSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
3-oxosteroid
12-hydroxysteroid
Hydroxysteroid
11-oxosteroid
15-oxosteroid
Oxosteroid
14-alpha-methylsteroid
12-alpha-hydroxysteroid
7-oxosteroid
3-oxo-5-alpha-steroid
Steroid
Fatty acid methyl ester
Fatty acid ester
Cyclohexenone
Fatty acyl
Methyl ester
Cyclic ketone
Ketone
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Organic oxygen 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	3.61	ChemAxon
pKa (Strongest Acidic)	12.9	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	114.81 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	128.97 m³·mol⁻¹	ChemAxon
Polarizability	53.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

162984416

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (4r)-4-[(1r,3ar,5ar,9as,11r,11ar)-11-hydroxy-3a,6,6,9a,11a-pentamethyl-3,4,7,10-tetraoxo-1h,2h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]pentanoate (NP0329235)

MOL for NP0329235 (methyl (4r)-4-[(1r,3ar,5ar,9as,11r,11ar)-11-hydroxy-3a,6,6,9a,11a-pentamethyl-3,4,7,10-tetraoxo-1h,2h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]pentanoate)

3D MOL for NP0329235 (methyl (4r)-4-[(1r,3ar,5ar,9as,11r,11ar)-11-hydroxy-3a,6,6,9a,11a-pentamethyl-3,4,7,10-tetraoxo-1h,2h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]pentanoate)

3D SDF for NP0329235 (methyl (4r)-4-[(1r,3ar,5ar,9as,11r,11ar)-11-hydroxy-3a,6,6,9a,11a-pentamethyl-3,4,7,10-tetraoxo-1h,2h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]pentanoate)

3D-SDF for NP0329235 (methyl (4r)-4-[(1r,3ar,5ar,9as,11r,11ar)-11-hydroxy-3a,6,6,9a,11a-pentamethyl-3,4,7,10-tetraoxo-1h,2h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]pentanoate)

PDB for NP0329235 (methyl (4r)-4-[(1r,3ar,5ar,9as,11r,11ar)-11-hydroxy-3a,6,6,9a,11a-pentamethyl-3,4,7,10-tetraoxo-1h,2h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]pentanoate)

3D PDB for NP0329235 (methyl (4r)-4-[(1r,3ar,5ar,9as,11r,11ar)-11-hydroxy-3a,6,6,9a,11a-pentamethyl-3,4,7,10-tetraoxo-1h,2h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]pentanoate)

SMILES for NP0329235 (methyl (4r)-4-[(1r,3ar,5ar,9as,11r,11ar)-11-hydroxy-3a,6,6,9a,11a-pentamethyl-3,4,7,10-tetraoxo-1h,2h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]pentanoate)

INCHI for NP0329235 (methyl (4r)-4-[(1r,3ar,5ar,9as,11r,11ar)-11-hydroxy-3a,6,6,9a,11a-pentamethyl-3,4,7,10-tetraoxo-1h,2h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]pentanoate)

Structure for NP0329235 (methyl (4r)-4-[(1r,3ar,5ar,9as,11r,11ar)-11-hydroxy-3a,6,6,9a,11a-pentamethyl-3,4,7,10-tetraoxo-1h,2h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]pentanoate)

3D Structure for NP0329235 (methyl (4r)-4-[(1r,3ar,5ar,9as,11r,11ar)-11-hydroxy-3a,6,6,9a,11a-pentamethyl-3,4,7,10-tetraoxo-1h,2h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]pentanoate)