NP-MRD: Showing NP-Card for 14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate (NP0233483)

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Record Information

Version

2.0

Created at

2022-09-06 15:06:14 UTC

Updated at

2022-09-06 15:06:14 UTC

NP-MRD ID

NP0233483

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate

Description

14-(Acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]Heptadeca-3,8,16-trien-12-yl benzoate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 14-(Acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]Heptadeca-3,8,16-trien-12-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251507082D          

 35 38  0  0  0  0            999 V2000
    0.6979   -0.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355   -1.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0406   -1.7794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4680   -1.7143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1630   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1254   -0.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203   -0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528   -0.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2477    0.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5904   -1.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3229   -1.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179   -1.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1524   -0.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5730    0.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9681   -0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3476    0.5307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3377   -0.9395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7504   -1.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7880   -2.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0931   -2.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1307   -3.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3606   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2382   -2.9179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758   -3.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083   -4.1216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5808   -4.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1910   -5.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1534   -4.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8483   -3.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8955   -1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2006   -2.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
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  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
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 12 18  1  0  0  0  0
 19 18  1  4  0  0  0
 19 20  2  0  0  0  0
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  5 34  1  0  0  0  0
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 34 35  1  0  0  0  0
M  END

     RDKit          3D

 69 72  0  0  0  0  0  0  0  0999 V2000
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   -3.4197   -1.1696    0.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0072    4.1457    0.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3900    4.1253    0.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3552    2.1927   -1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3816    1.3283    0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4146   -1.2724   -2.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004251507082D          

 35 38  0  0  0  0            999 V2000
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 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233483

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC=C(C)C2CC3=C(C)C(=O)OC3C=C(C)CCC(OC(=O)C3=CC=CC=C3)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O6/c1-17-11-13-26(35-28(32)21-9-7-6-8-10-21)29(5)23(18(2)12-14-25(29)33-20(4)30)16-22-19(3)27(31)34-24(22)15-17/h6-10,12,15,23-26H,11,13-14,16H2,1-5H3

> <INCHI_KEY>
BYTXNCPKVDXTRC-UHFFFAOYSA-N

> <FORMULA>
C29H34O6

> <MOLECULAR_WEIGHT>
478.585

> <EXACT_MASS>
478.235538815

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.47239754742066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate

> <ALOGPS_LOGP>
4.95

> <JCHEM_LOGP>
5.5668287466666655

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.678665242537697

> <JCHEM_PKA_STRONGEST_BASIC>
-6.452993985777959

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
133.6519

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       1.303  -0.953   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.373  -2.492   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.076  -3.322   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.740  -3.200   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.038  -2.370   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.967  -0.832   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.265  -0.002   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.632  -0.710   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.929   0.120   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.702  -2.248   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.069  -2.957   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.367  -2.127   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.618  -0.607   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.536   0.489   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.141  -0.377   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.849   0.991   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      11.830  -1.754   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.734  -2.835   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.804  -4.374   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.507  -5.204   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.577  -6.742   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.140  -4.495   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.843  -5.325   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.475  -4.617   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.178  -5.447   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.248  -6.985   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.616  -7.694   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.951  -7.815   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.021  -9.354   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.724 -10.184   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.357  -9.475   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.286  -7.937   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.584  -7.107   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.405  -3.078   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.108  -3.908   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   34                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   34                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   24    5   10   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
14-(Acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0,]heptadeca-3,8,16-trien-12-yl benzoic acid	Generator
14-(Acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoic acid	Generator

Chemical Formula

C₂₉H₃₄O₆

Average Mass

478.5850 Da

Monoisotopic Mass

478.23554 Da

IUPAC Name

14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate

Traditional Name

14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC=C(C)C2CC3=C(C)C(=O)OC3C=C(C)CCC(OC(=O)C3=CC=CC=C3)C12C

InChI Identifier

InChI=1S/C29H34O6/c1-17-11-13-26(35-28(32)21-9-7-6-8-10-21)29(5)23(18(2)12-14-25(29)33-20(4)30)16-22-19(3)27(31)34-24(22)15-17/h6-10,12,15,23-26H,11,13-14,16H2,1-5H3

InChI Key

BYTXNCPKVDXTRC-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Briarane diterpenoid
Diterpene lactone
Diterpenoid
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Monocyclic benzene moiety
2-furanone
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4.95	ALOGPS
logP	5.57	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	13.68	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	133.65 m³·mol⁻¹	ChemAxon
Polarizability	51.47 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

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

85235823

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate (NP0233483)

MOL for NP0233483 (14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate)

3D MOL for NP0233483 (14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate)

3D SDF for NP0233483 (14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate)

3D-SDF for NP0233483 (14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate)

PDB for NP0233483 (14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate)

3D PDB for NP0233483 (14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate)

SMILES for NP0233483 (14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate)

INCHI for NP0233483 (14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate)

Structure for NP0233483 (14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate)

3D Structure for NP0233483 (14-(acetyloxy)-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-3,8,16-trien-12-yl benzoate)