NP-MRD: Showing NP-Card for 6-{7,11-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,4,10-trioxo-5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid (NP0150648)

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Record Information

Version

2.0

Created at

2022-09-02 06:49:37 UTC

Updated at

2022-09-02 06:49:38 UTC

NP-MRD ID

NP0150648

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-{7,11-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,4,10-trioxo-5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid

Description

6-{7,11-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,4,10-trioxo-5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid is found in Ganoderma resinaceum. Based on a literature review very few articles have been published on 6-{5,16-dihydroxy-2,6,6,11,15-pentamethyl-9,12,17-trioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-1(10),13-dien-14-yl}-2-methyl-4-oxoheptanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022208492D          

 38 41  0  0  0  0            999 V2000
    1.6704   -2.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2415   -3.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4730   -4.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -3.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6556   -3.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2077   -4.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7952   -5.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  9 21  1  0  0  0  0
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 34 35  2  0  0  0  0
  2 36  1  0  0  0  0
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 36 38  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309022208492D          

 38 41  0  0  0  0            999 V2000
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   -3.8149   -8.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3228   -8.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5433   -7.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5600   -7.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1120   -6.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8571   -6.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4091   -5.4711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849   -4.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0993   -3.7235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849   -4.9610    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  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  0  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  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  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  1  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  0  0  0  0
 33 34  1  0  0  0  0
 15 34  1  0  0  0  0
 34 35  2  0  0  0  0
  2 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0150648

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC(=O)CC(C)C1=CC(=O)C2(C)C3=C(C(=O)C(O)C12C)C1(C)CCC(O)C(C)(C)C1CC3=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O8/c1-14(10-16(31)11-15(2)26(37)38)17-12-21(34)30(7)22-18(32)13-19-27(3,4)20(33)8-9-28(19,5)23(22)24(35)25(36)29(17,30)6/h12,14-15,19-20,25,33,36H,8-11,13H2,1-7H3,(H,37,38)

> <INCHI_KEY>
XOWZEGQXFDYEEB-UHFFFAOYSA-N

> <FORMULA>
C30H40O8

> <MOLECULAR_WEIGHT>
528.642

> <EXACT_MASS>
528.272318248

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
55.93809311182669

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-{5,16-dihydroxy-2,6,6,11,15-pentamethyl-9,12,17-trioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),13-dien-14-yl}-2-methyl-4-oxoheptanoic acid

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
3.1059168143333347

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.84243878469439

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.127207880198447

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7785746631173852

> <JCHEM_POLAR_SURFACE_AREA>
146.04

> <JCHEM_REFRACTIVITY>
140.27190000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{5,16-dihydroxy-2,6,6,11,15-pentamethyl-9,12,17-trioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),13-dien-14-yl}-2-methyl-4-oxoheptanoic acid

> <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       3.118  -5.411   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.118  -6.951   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.784  -7.721   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.451  -6.951   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.451  -5.411   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.883  -7.721   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.217  -6.951   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.217  -5.411   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.550  -7.721   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.957  -7.094   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.988  -8.239   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -7.519  -8.078   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.218  -9.572   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.749  -9.733   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.694 -11.037   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.663 -12.181   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.157 -11.861   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.126 -13.006   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.681 -10.397   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.174 -10.076   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.711  -9.252   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.247  -8.776   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.139 -13.646   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.633 -13.326   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.108 -14.790   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.584 -16.255   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.091 -16.575   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.567 -18.040   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -7.121 -15.431   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.069 -16.644   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -8.481 -14.708   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.645 -13.966   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -7.676 -12.822   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.200 -11.357   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -8.230 -10.213   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.452  -7.721   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.785  -6.951   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       4.452  -9.261   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    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                                                            
CONECT   36    2   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
6-{5,16-dihydroxy-2,6,6,11,15-pentamethyl-9,12,17-trioxotetracyclo[8.7.0.0,.0,]heptadeca-1(10),13-dien-14-yl}-2-methyl-4-oxoheptanoate	Generator

Chemical Formula

C₃₀H₄₀O₈

Average Mass

528.6420 Da

Monoisotopic Mass

528.27232 Da

IUPAC Name

6-{5,16-dihydroxy-2,6,6,11,15-pentamethyl-9,12,17-trioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),13-dien-14-yl}-2-methyl-4-oxoheptanoic acid

Traditional Name

6-{5,16-dihydroxy-2,6,6,11,15-pentamethyl-9,12,17-trioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),13-dien-14-yl}-2-methyl-4-oxoheptanoic acid

CAS Registry Number

Not Available

SMILES

CC(CC(=O)CC(C)C1=CC(=O)C2(C)C3=C(C(=O)C(O)C12C)C1(C)CCC(O)C(C)(C)C1CC3=O)C(O)=O

InChI Identifier

InChI=1S/C30H40O8/c1-14(10-16(31)11-15(2)26(37)38)17-12-21(34)30(7)22-18(32)13-19-27(3,4)20(33)8-9-28(19,5)23(22)24(35)25(36)29(17,30)6/h12,14-15,19-20,25,33,36H,8-11,13H2,1-7H3,(H,37,38)

InChI Key

XOWZEGQXFDYEEB-UHFFFAOYSA-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
Ganoderma resinaceum	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	3.18	ALOGPS
logP	3.11	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.13	ChemAxon
pKa (Strongest Basic)	-0.78	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	146.04 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	140.27 m³·mol⁻¹	ChemAxon
Polarizability	55.94 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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

162815088

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-{7,11-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,4,10-trioxo-5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid (NP0150648)

MOL for NP0150648 (6-{7,11-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,4,10-trioxo-5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

3D MOL for NP0150648 (6-{7,11-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,4,10-trioxo-5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

3D SDF for NP0150648 (6-{7,11-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,4,10-trioxo-5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

3D-SDF for NP0150648 (6-{7,11-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,4,10-trioxo-5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

PDB for NP0150648 (6-{7,11-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,4,10-trioxo-5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

3D PDB for NP0150648 (6-{7,11-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,4,10-trioxo-5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

SMILES for NP0150648 (6-{7,11-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,4,10-trioxo-5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

INCHI for NP0150648 (6-{7,11-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,4,10-trioxo-5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

Structure for NP0150648 (6-{7,11-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,4,10-trioxo-5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

3D Structure for NP0150648 (6-{7,11-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,4,10-trioxo-5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)