NP-MRD: Showing NP-Card for methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate (NP0327501)

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Record Information

Version

1.0

Created at

2022-09-12 10:08:00 UTC

Updated at

2022-09-12 10:08:00 UTC

NP-MRD ID

NP0327501

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate

Description

Methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]Icosa-13,16,18-triene-16-carboxylate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]Icosa-13,16,18-triene-16-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171520432D          

 36 39  0  0  0  0            999 V2000
    0.9956   -2.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7719   -2.0712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4018   -2.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2553   -3.4159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1782   -2.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7664   -2.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5005   -3.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5854   -2.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0185   -2.1019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8303   -2.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3632   -1.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0841   -0.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8051   -0.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6170   -0.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4289   -0.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7079   -1.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5326   -1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3723   -0.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5966   -2.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2723   -0.6957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8592   -0.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5614   -1.0714    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
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  9 32  1  0  0  0  0
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 33 35  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END

     RDKit          3D

 72 75  0  0  0  0  0  0  0  0999 V2000
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   -0.0892   -1.2709   -0.8083 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.1197   -2.3435   -0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004171520432D          

 36 39  0  0  0  0            999 V2000
    0.9956   -2.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 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
 24 29  1  0  0  0  0
 11 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0327501

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C(C)C=C2CC3C(C)(CCC4C3(C)C(CC(=O)OC4(C)C)OC(C)=O)OC2=C(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O8/c1-14-11-17-12-19-27(6,36-24(17)15(2)23(31)22(14)25(32)33-8)10-9-18-26(4,5)35-21(30)13-20(28(18,19)7)34-16(3)29/h11,18-20H,9-10,12-13H2,1-8H3

> <INCHI_KEY>
DYUKFMAGTDRGEF-UHFFFAOYSA-N

> <FORMULA>
C28H36O8

> <MOLECULAR_WEIGHT>
500.588

> <EXACT_MASS>
500.241018119

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.99497071426348

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate

> <ALOGPS_LOGP>
4.27

> <JCHEM_LOGP>
3.245504990333332

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.719284442913905

> <JCHEM_POLAR_SURFACE_AREA>
105.20000000000002

> <JCHEM_REFRACTIVITY>
132.64960000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate

> <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       1.858  -4.387   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.308  -3.866   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.483  -4.861   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.210  -6.376   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.933  -4.340   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.031  -5.420   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.534  -6.877   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.559  -5.234   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.368  -3.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.883  -4.197   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.878  -3.021   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.357  -1.572   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.836  -0.123   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.352  -0.396   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.867  -0.670   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.388  -2.119   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.927  -2.164   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.628  -0.653   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.334  -1.536   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.852  -3.395   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      16.466  -4.886   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      17.642  -5.881   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      15.060  -5.514   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.693  -4.806   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.461  -5.730   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.647  -7.259   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.063  -7.863   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.415  -8.184   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.393  -3.295   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.314  -4.393   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.842  -1.299   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.847  -2.474   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.389  -1.978   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.204  -0.449   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.092  -2.808   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.781  -2.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   35                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   29                                                  
CONECT   12   11   13   14   31                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   11   16   30                                             
CONECT   30   29                                                            
CONECT   31   12   32                                                       
CONECT   32   31    9   33                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    5   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0,.0,]icosa-13,16,18-triene-16-carboxylic acid	Generator
Methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylic acid	Generator

Chemical Formula

C₂₈H₃₆O₈

Average Mass

500.5880 Da

Monoisotopic Mass

500.24102 Da

IUPAC Name

methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate

Traditional Name

methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C(C)C=C2CC3C(C)(CCC4C3(C)C(CC(=O)OC4(C)C)OC(C)=O)OC2=C(C)C1=O

InChI Identifier

InChI=1S/C28H36O8/c1-14-11-17-12-19-27(6,36-24(17)15(2)23(31)22(14)25(32)33-8)10-9-18-26(4,5)35-21(30)13-20(28(18,19)7)34-16(3)29/h11,18-20H,9-10,12-13H2,1-8H3

InChI Key

DYUKFMAGTDRGEF-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 tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Caprolactone
Tropone
Alkyl aryl ether
Oxepane
Methyl ester
Vinylogous ester
Lactone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxide
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	4.27	ALOGPS
logP	3.25	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	105.2 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	132.65 m³·mol⁻¹	ChemAxon
Polarizability	53.99 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

73239198

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate (NP0327501)

MOL for NP0327501 (methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate)

3D MOL for NP0327501 (methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate)

3D SDF for NP0327501 (methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate)

3D-SDF for NP0327501 (methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate)

PDB for NP0327501 (methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate)

3D PDB for NP0327501 (methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate)

SMILES for NP0327501 (methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate)

INCHI for NP0327501 (methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate)

Structure for NP0327501 (methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate)

3D Structure for NP0327501 (methyl 3-(acetyloxy)-2,7,7,11,14,17-hexamethyl-5,15-dioxo-6,12-dioxatetracyclo[9.9.0.0²,⁸.0¹³,¹⁹]icosa-13,16,18-triene-16-carboxylate)