NP-MRD: Showing NP-Card for (1s,2s,3ar,7s,11r,13as)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,7h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0154735)

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Record Information

Version

2.0

Created at

2022-09-02 11:41:11 UTC

Updated at

2022-09-02 11:41:12 UTC

NP-MRD ID

NP0154735

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3ar,7s,11r,13as)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,7h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate

Description

Euphoheliosnoid D belongs to the class of organic compounds known as jatrophane and cyclojatrophane diterpenoids. These are diterpenoids with a structure based on the jatrophane or the 9,13-jatrophane skeleton. Jatrophane can be derived from casbane by 6,10-cyclization and opening of the cyclopropane. Cyclojatrophane diterpenoids are based on the 9,13-cyclization of the jatrophane skeleton yields the 9,13-cyclojatrophane skeleton. (1s,2s,3ar,7s,11r,13as)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,7h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate is found in Euphorbia helioscopia. (1s,2s,3ar,7s,11r,13as)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,7h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate was first documented in 2006 (PMID: 16819227). Based on a literature review very few articles have been published on Euphoheliosnoid D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022213412D          

 37 39  0  0  1  0            999 V2000
   -0.3516   -2.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4404   -2.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006   -1.7935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022213412D          

 37 39  0  0  1  0            999 V2000
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    2.6598   -2.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3199   -1.9916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8766   -3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7097   -3.8107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  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  2  0  0  0  0
 14 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
 13 18  1  0  0  0  0
  9 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 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  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0154735

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@@]2(OC(C)=O)[C@@H](\C=C(C)\[C@H](O)CC(=O)C(C)(C)[C@@H](O)\C=C(C)\C2=O)[C@H]1OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O8/c1-16-12-21-25(36-27(35)20-10-8-7-9-11-20)18(3)15-29(21,37-19(4)30)26(34)17(2)13-23(32)28(5,6)24(33)14-22(16)31/h7-13,18,21-23,25,31-32H,14-15H2,1-6H3/b16-12+,17-13+/t18-,21-,22+,23-,25-,29+/m0/s1

> <INCHI_KEY>
LRHZYZQQBGOKEN-YZQLQQNVSA-N

> <FORMULA>
C29H36O8

> <MOLECULAR_WEIGHT>
512.599

> <EXACT_MASS>
512.241018119

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.922146033939526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3aR,7S,11R,13aS)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1H,2H,3H,3aH,4H,7H,8H,9H,10H,11H,13aH-cyclopenta[12]annulen-1-yl benzoate

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
4.142101059000002

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.609324074909239

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.946267262920273

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0425843873900025

> <JCHEM_POLAR_SURFACE_AREA>
127.20000000000002

> <JCHEM_REFRACTIVITY>
137.55700000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.06e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3aR,7S,11R,13aS)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1H,2H,3H,7H,10H,11H,13aH-cyclopenta[12]annulen-1-yl benzoate

> <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      -0.656  -5.239   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.381  -6.377   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.087  -7.845   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.885  -6.049   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.353  -4.581   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.822  -4.751   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.188  -3.348   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.320  -3.036   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.326  -2.311   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.157  -0.780   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.254  -0.162   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.495  -1.074   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.424   1.369   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.834   1.987   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.004   3.518   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.763   4.430   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.647   3.812   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.817   2.281   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.664  -3.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.126  -2.589   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.438  -1.081   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.287  -0.057   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.900  -0.597   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.211   0.912   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.050  -1.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.738  -3.129   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.276  -3.613   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.889  -4.152   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.697  -2.842   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.320  -4.721   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.577  -5.661   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.727  -6.685   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.115  -6.145   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.965  -5.121   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.331  -3.718   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.503  -5.605   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.191  -7.113   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   19   36                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    9    5   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    5   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₈

Average Mass

512.5990 Da

Monoisotopic Mass

512.24102 Da

IUPAC Name

(1S,2S,3aR,7S,11R,13aS)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1H,2H,3H,3aH,4H,7H,8H,9H,10H,11H,13aH-cyclopenta[12]annulen-1-yl benzoate

Traditional Name

(1S,2S,3aR,7S,11R,13aS)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1H,2H,3H,7H,10H,11H,13aH-cyclopenta[12]annulen-1-yl benzoate

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@@]2(OC(C)=O)[C@@H](\C=C(C)\[C@H](O)CC(=O)C(C)(C)[C@@H](O)\C=C(C)\C2=O)[C@H]1OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C29H36O8/c1-16-12-21-25(36-27(35)20-10-8-7-9-11-20)18(3)15-29(21,37-19(4)30)26(34)17(2)13-23(32)28(5,6)24(33)14-22(16)31/h7-13,18,21-23,25,31-32H,14-15H2,1-6H3/b16-12+,17-13+/t18-,21-,22+,23-,25-,29+/m0/s1

InChI Key

LRHZYZQQBGOKEN-YZQLQQNVSA-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
Euphorbia helioscopia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as jatrophane and cyclojatrophane diterpenoids. These are diterpenoids with a structure based on the jatrophane or the 9,13-jatrophane skeleton. Jatrophane can be derived from casbane by 6,10-cyclization and opening of the cyclopropane. Cyclojatrophane diterpenoids are based on the 9,13-cyclization of the jatrophane skeleton yields the 9,13-cyclojatrophane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Jatrophane and cyclojatrophane diterpenoids

Alternative Parents

Substituents

Jatrophane diterpenoid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Alpha-acyloxy ketone
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	2.57	ALOGPS
logP	4.14	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	13.95	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	127.2 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	137.56 m³·mol⁻¹	ChemAxon
Polarizability	52.92 Å³	ChemAxon
Number of Rings	3	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

C00030231

Chemspider ID

17238951

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16079976

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang W, Guo YW: Chemical studies on the constituents of the chinese medicinal herb Euphorbia helioscopia L. Chem Pharm Bull (Tokyo). 2006 Jul;54(7):1037-9. doi: 10.1248/cpb.54.1037. [PubMed:16819227 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,3ar,7s,11r,13as)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,7h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0154735)

MOL for NP0154735 ((1s,2s,3ar,7s,11r,13as)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,7h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D MOL for NP0154735 ((1s,2s,3ar,7s,11r,13as)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,7h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D SDF for NP0154735 ((1s,2s,3ar,7s,11r,13as)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,7h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D-SDF for NP0154735 ((1s,2s,3ar,7s,11r,13as)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,7h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

PDB for NP0154735 ((1s,2s,3ar,7s,11r,13as)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,7h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D PDB for NP0154735 ((1s,2s,3ar,7s,11r,13as)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,7h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

SMILES for NP0154735 ((1s,2s,3ar,7s,11r,13as)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,7h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

INCHI for NP0154735 ((1s,2s,3ar,7s,11r,13as)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,7h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

Structure for NP0154735 ((1s,2s,3ar,7s,11r,13as)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,7h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D Structure for NP0154735 ((1s,2s,3ar,7s,11r,13as)-3a-(acetyloxy)-7,11-dihydroxy-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,7h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)