NP-MRD: Showing NP-Card for 3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0326500)

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Record Information

Version

2.0

Created at

2022-09-12 08:06:34 UTC

Updated at

2022-09-12 08:06:35 UTC

NP-MRD ID

NP0326500

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate

Description

3A,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,13aH-cyclopenta[12]annulen-1-yl benzoate 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. 3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate is found in Euphorbia helioscopia. 3A,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,13aH-cyclopenta[12]annulen-1-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171518132D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004171518132D          

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    4.1106    0.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2775    1.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7268    0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7105   -1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6196   -0.4180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1360   -0.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8007   -0.5754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269    0.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9825    1.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0734    1.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4088    2.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3468    2.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4377    1.2220    0.0000 C   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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 20 17  1  4  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  2  0  0  0  0
 13 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
  9 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326500

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2(OC(C)=O)C(C=C(C)C(CC(=O)C(C)(C)C=CC(C)C2=O)OC(C)=O)C1OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O8/c1-18-13-14-30(6,7)26(34)16-25(37-21(4)32)19(2)15-24-27(38-29(36)23-11-9-8-10-12-23)20(3)17-31(24,28(18)35)39-22(5)33/h8-15,18,20,24-25,27H,16-17H2,1-7H3

> <INCHI_KEY>
VWSCEDLUJPCZIA-UHFFFAOYSA-N

> <FORMULA>
C31H38O8

> <MOLECULAR_WEIGHT>
538.637

> <EXACT_MASS>
538.256668184

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
56.92237411512625

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
5.445820719

> <ALOGPS_LOGS>
-5.70

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.28361778025202

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.080205541344274

> <JCHEM_PKA_STRONGEST_BASIC>
-6.459128064338817

> <JCHEM_POLAR_SURFACE_AREA>
113.04000000000002

> <JCHEM_REFRACTIVITY>
145.58769999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -1.320  -3.036   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.188  -3.348   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.822  -4.751   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.353  -4.581   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.885  -6.049   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.381  -6.377   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.087  -7.845   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.656  -5.239   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.664  -3.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.126  -2.589   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.438  -1.081   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.287  -0.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.900  -0.597   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.050  -1.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.738  -3.129   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.276  -3.613   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.889  -4.152   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.320  -4.721   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.697  -2.842   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.577  -5.661   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.115  -6.145   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.965  -5.121   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.331  -3.718   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.503  -5.605   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.191  -7.113   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.211   0.912   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.673   1.396   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.985   2.904   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.823   0.372   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.326  -2.311   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.157  -0.780   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.254  -0.162   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.495  -1.074   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.424   1.369   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.834   1.987   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.004   3.518   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.763   4.430   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.647   3.812   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.817   2.281   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9   24                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10   30                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    4   25                                                  
CONECT   25   24                                                            
CONECT   26   13   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    9    2   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   34                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Value	Source
3a,11-Bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1H,2H,3H,3ah,4H,5H,8H,9H,10H,11H,13ah-cyclopenta[12]annulen-1-yl benzoic acid	Generator

Chemical Formula

C₃₁H₃₈O₈

Average Mass

538.6370 Da

Monoisotopic Mass

538.25667 Da

IUPAC Name

3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,13aH-cyclopenta[12]annulen-1-yl benzoate

Traditional Name

3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1H,2H,3H,5H,10H,11H,13aH-cyclopenta[12]annulen-1-yl benzoate

CAS Registry Number

Not Available

SMILES

CC1CC2(OC(C)=O)C(C=C(C)C(CC(=O)C(C)(C)C=CC(C)C2=O)OC(C)=O)C1OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C31H38O8/c1-18-13-14-30(6,7)26(34)16-25(37-21(4)32)19(2)15-24-27(38-29(36)23-11-9-8-10-12-23)20(3)17-31(24,28(18)35)39-22(5)33/h8-15,18,20,24-25,27H,16-17H2,1-7H3

InChI Key

VWSCEDLUJPCZIA-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
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
Tricarboxylic acid or derivatives
Benzoyl
Alpha-acyloxy ketone
Monocyclic benzene moiety
Benzenoid
Ketone
Carboxylic acid ester
Cyclic ketone
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen 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	3.46	ALOGPS
logP	5.45	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	15.08	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	113.04 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	145.59 m³·mol⁻¹	ChemAxon
Polarizability	56.92 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate (NP0326500)

MOL for NP0326500 (3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D MOL for NP0326500 (3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D SDF for NP0326500 (3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D-SDF for NP0326500 (3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

PDB for NP0326500 (3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D PDB for NP0326500 (3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

SMILES for NP0326500 (3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

INCHI for NP0326500 (3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

Structure for NP0326500 (3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)

3D Structure for NP0326500 (3a,11-bis(acetyloxy)-2,5,8,8,12-pentamethyl-4,9-dioxo-1h,2h,3h,5h,10h,11h,13ah-cyclopenta[12]annulen-1-yl benzoate)