NP-MRD: Showing NP-Card for (2e)-4-hydroxy-2-methyl-6-{4,7,11-trihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}hept-2-enoic acid (NP0241708)

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Record Information

Version

2.0

Created at

2022-09-07 01:51:28 UTC

Updated at

2022-09-07 01:51:29 UTC

NP-MRD ID

NP0241708

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-4-hydroxy-2-methyl-6-{4,7,11-trihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}hept-2-enoic acid

Description

Centellasapogenol A belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Centellasapogenol A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Centellasapogenol A has been detected, but not quantified in, green vegetables. This could make centellasapogenol a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241218202D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02241218202D          

 38 41  0  0  0  0            999 V2000
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    0.3838    1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3315    1.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0991    1.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8144    1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5297    1.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2451    1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    1.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8144    0.6872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2451    0.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6758    1.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    2.7505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6397   -1.4230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1073    1.6707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  1  0  0  0  0
  3 20  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 21  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 23  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 24  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 25  1  0  0  0  0
 13 14  1  0  0  0  0
 13 38  1  0  0  0  0
 14 22  2  0  0  0  0
 15 16  1  0  0  0  0
 15 37  2  0  0  0  0
 16 17  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 33  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 34  1  0  0  0  0
 32 35  1  0  0  0  0
 32 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0241708

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC(O)\C=C(/C)C(O)=O)C1CC(=O)C2(C)C3=C(C(=O)C(O)C12C)C1(C)CCC(O)C(C)(C)C1CC3O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O8/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/h11,14,16-20,25,31-33,36H,8-10,12-13H2,1-7H3,(H,37,38)/b15-11+

> <INCHI_KEY>
SFQSUCWHIWDMMD-RVDMUPIBSA-N

> <FORMULA>
C30H44O8

> <MOLECULAR_WEIGHT>
532.6656

> <EXACT_MASS>
532.303618384

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
58.09603479784006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-hydroxy-2-methyl-6-{5,9,16-trihydroxy-2,6,6,11,15-pentamethyl-12,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}hept-2-enoic acid

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.3870178026666666

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.88967495692696

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.330953268924337

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8070082167490703

> <JCHEM_POLAR_SURFACE_AREA>
152.35999999999999

> <JCHEM_REFRACTIVITY>
142.01750000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-4-hydroxy-2-methyl-6-{5,9,16-trihydroxy-2,6,6,11,15-pentamethyl-12,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}hept-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.393  -1.488   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.393  -3.028   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.060  -3.799   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.730  -3.028   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.730  -1.488   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.060  -0.720   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.397  -3.799   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.067  -3.028   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.067  -1.488   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.397  -0.720   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.740  -0.720   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.740   0.813   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.067   1.578   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.397   0.813   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.716  -1.193   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.612   0.048   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.716   1.283   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -8.728  -3.799   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.830  -5.134   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.290  -5.134   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.730   0.053   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.730   1.583   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.732  -3.799   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.740  -2.261   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.740   2.354   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.716   2.823   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.619   3.594   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.052   3.594   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.387   2.823   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.722   3.594   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.058   2.823   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.393   3.594   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.387   1.283   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.058   1.283   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.728   2.823   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       7.393   5.134   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       1.194  -2.656   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -2.067   3.119   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4   19   20                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   21                                             
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14                                                  
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   25                                             
CONECT   13   12   14   38                                                  
CONECT   14   10   13   22                                                  
CONECT   15   11   16   37                                                  
CONECT   16   15   17                                                       
CONECT   17   12   16   26                                                  
CONECT   18    2                                                            
CONECT   19    3                                                            
CONECT   20    3                                                            
CONECT   21    5                                                            
CONECT   22   14                                                            
CONECT   23    8                                                            
CONECT   24   11                                                            
CONECT   25   12                                                            
CONECT   26   17   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   34                                                  
CONECT   32   31   35   36                                                  
CONECT   33   29                                                            
CONECT   34   31                                                            
CONECT   35   32                                                            
CONECT   36   32                                                            
CONECT   37   15                                                            
CONECT   38   13                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
(+)-Ganoderic acid eta	HMDB
(2E)-4-Hydroxy-2-methyl-6-{5,9,16-trihydroxy-2,6,6,11,15-pentamethyl-12,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}hept-2-enoate	Generator
Ganoderate eta	Generator
Ganoderate η	Generator
Ganoderic acid η	Generator

Chemical Formula

C₃₀H₄₄O₈

Average Mass

532.6656 Da

Monoisotopic Mass

532.30362 Da

IUPAC Name

(2E)-4-hydroxy-2-methyl-6-{5,9,16-trihydroxy-2,6,6,11,15-pentamethyl-12,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}hept-2-enoic acid

Traditional Name

(2E)-4-hydroxy-2-methyl-6-{5,9,16-trihydroxy-2,6,6,11,15-pentamethyl-12,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}hept-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC(CC(O)\C=C(/C)C(O)=O)C1CC(=O)C2(C)C3=C(C(=O)C(O)C12C)C1(C)CCC(O)C(C)(C)C1CC3O

InChI Identifier

InChI=1S/C30H44O8/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/h11,14,16-20,25,31-33,36H,8-10,12-13H2,1-7H3,(H,37,38)/b15-11+

InChI Key

SFQSUCWHIWDMMD-RVDMUPIBSA-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
12-hydroxysteroid
Hydroxysteroid
Steroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
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	2.36	ALOGPS
logP	2.39	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.33	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	152.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	142.02 m³·mol⁻¹	ChemAxon
Polarizability	58.1 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	No	ChemAxon

External Links

HMDB ID

HMDB0036311

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015180

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

73196815

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-4-hydroxy-2-methyl-6-{4,7,11-trihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}hept-2-enoic acid (NP0241708)

MOL for NP0241708 ((2e)-4-hydroxy-2-methyl-6-{4,7,11-trihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}hept-2-enoic acid)

3D MOL for NP0241708 ((2e)-4-hydroxy-2-methyl-6-{4,7,11-trihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}hept-2-enoic acid)

3D SDF for NP0241708 ((2e)-4-hydroxy-2-methyl-6-{4,7,11-trihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}hept-2-enoic acid)

3D-SDF for NP0241708 ((2e)-4-hydroxy-2-methyl-6-{4,7,11-trihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}hept-2-enoic acid)

PDB for NP0241708 ((2e)-4-hydroxy-2-methyl-6-{4,7,11-trihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}hept-2-enoic acid)

3D PDB for NP0241708 ((2e)-4-hydroxy-2-methyl-6-{4,7,11-trihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}hept-2-enoic acid)

SMILES for NP0241708 ((2e)-4-hydroxy-2-methyl-6-{4,7,11-trihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}hept-2-enoic acid)

INCHI for NP0241708 ((2e)-4-hydroxy-2-methyl-6-{4,7,11-trihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}hept-2-enoic acid)

Structure for NP0241708 ((2e)-4-hydroxy-2-methyl-6-{4,7,11-trihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}hept-2-enoic acid)

3D Structure for NP0241708 ((2e)-4-hydroxy-2-methyl-6-{4,7,11-trihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}hept-2-enoic acid)