NP-MRD: Showing NP-Card for {11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate (NP0288331)

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Record Information

Version

2.0

Created at

2022-09-09 17:59:29 UTC

Updated at

2022-09-09 17:59:29 UTC

NP-MRD ID

NP0288331

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate

Description

{11-[(Benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]Dodeca-5,9-dien-3-yl}methyl benzoate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. {11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate is found in Uvaria grandiflora and Uvaria rufa. {11-[(Benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]Dodeca-5,9-dien-3-yl}methyl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231517402D          

 36 40  0  0  0  0            999 V2000
    2.1811    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542    1.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5845    2.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3023    3.1335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3969    2.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9272    2.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7397    2.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0219    1.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4916    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6791    1.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5680    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    1.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2445    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7748    1.3137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8694    0.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6819    0.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5680   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465   -0.4125    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
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  7 12  1  0  0  0  0
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 23 35  1  0  0  0  0
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M  END

     RDKit          3D

 60 64  0  0  0  0  0  0  0  0999 V2000
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    0.1469   -1.9056   -0.3755 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6170   -1.5058    1.4005 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0026   -0.5981    2.1959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1188   -1.2381    1.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4358    0.0381    0.9565 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0070   -0.8324    1.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1481    0.9026   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004231517402D          

 36 40  0  0  0  0            999 V2000
    2.1811    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542    1.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0288331

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1(COC(=O)C2=CC=CC=C2)C2C(C=CC1=O)C1C=CC2C(O)(COC(=O)C2=CC=CC=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H24O8/c29-22-14-12-19-20-11-13-21(23(19)28(22,34)16-36-26(32)18-9-5-2-6-10-18)27(33,24(20)30)15-35-25(31)17-7-3-1-4-8-17/h1-14,19-21,23,33-34H,15-16H2

> <INCHI_KEY>
XXUFTPBMJHFXJE-UHFFFAOYSA-N

> <FORMULA>
C28H24O8

> <MOLECULAR_WEIGHT>
488.492

> <EXACT_MASS>
488.147117733

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
49.225918853906855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
3.486694619

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.31278997230698

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.684010312411388

> <JCHEM_PKA_STRONGEST_BASIC>
-4.096909360382445

> <JCHEM_POLAR_SURFACE_AREA>
127.19999999999999

> <JCHEM_REFRACTIVITY>
129.90500000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  O   UNK     0       4.071   3.490   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.061   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.051   3.490   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.568   3.222   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.558   4.402   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.031   5.849   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.074   4.135   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.064   5.314   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.581   5.047   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.107   3.600   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.118   2.420   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.601   2.687   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.728   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.728   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.061  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.395  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.395   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.729   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.394  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.137   0.257   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.137   1.283   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.394   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.060   1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.534   2.987   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.456   1.273   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.446   2.452   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.963   2.185   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.953   3.365   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.490   0.738   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.500  -0.442   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.026  -1.889   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.543  -2.157   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.533  -0.977   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.006   0.470   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.060  -0.000   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.273  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13   17                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    2   14   22                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    2   18                                                  
CONECT   18   17                                                            
CONECT   19   14   20   35                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   13   23                                                  
CONECT   23   22   24   25   35                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   23   19   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
{11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0,]dodeca-5,9-dien-3-yl}methyl benzoic acid	Generator
{11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoic acid	Generator

Chemical Formula

C₂₈H₂₄O₈

Average Mass

488.4920 Da

Monoisotopic Mass

488.14712 Da

IUPAC Name

{11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate

Traditional Name

{11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate

CAS Registry Number

Not Available

SMILES

OC1(COC(=O)C2=CC=CC=C2)C2C(C=CC1=O)C1C=CC2C(O)(COC(=O)C2=CC=CC=C2)C1=O

InChI Identifier

InChI=1S/C28H24O8/c29-22-14-12-19-20-11-13-21(23(19)28(22,34)16-36-26(32)18-9-5-2-6-10-18)27(33,24(20)30)15-35-25(31)17-7-3-1-4-8-17/h1-14,19-21,23,33-34H,15-16H2

InChI Key

XXUFTPBMJHFXJE-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
Uvaria grandiflora	LOTUS Database	35616633
Uvaria rufa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
Cyclohexenone
Acyloin
Dicarboxylic acid or derivatives
Tertiary alcohol
Cyclic alcohol
Ketone
Carboxylic acid ester
Cyclic ketone
Carboxylic acid derivative
Organooxygen compound
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	2.04	ALOGPS
logP	3.49	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	11.68	ChemAxon
pKa (Strongest Basic)	-4.1	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	8	ChemAxon
Refractivity	129.9 m³·mol⁻¹	ChemAxon
Polarizability	49.23 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

73322603

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate (NP0288331)

MOL for NP0288331 ({11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate)

3D MOL for NP0288331 ({11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate)

3D SDF for NP0288331 ({11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate)

3D-SDF for NP0288331 ({11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate)

PDB for NP0288331 ({11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate)

3D PDB for NP0288331 ({11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate)

SMILES for NP0288331 ({11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate)

INCHI for NP0288331 ({11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate)

Structure for NP0288331 ({11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate)

3D Structure for NP0288331 ({11-[(benzoyloxy)methyl]-3,11-dihydroxy-4,12-dioxotricyclo[6.2.2.0²,⁷]dodeca-5,9-dien-3-yl}methyl benzoate)