NP-MRD: Showing NP-Card for 7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid (NP0192330)

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Record Information

Version

2.0

Created at

2022-09-04 09:30:56 UTC

Updated at

2022-09-04 09:30:56 UTC

NP-MRD ID

NP0192330

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid

Description

7-(3,3-Dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalene-1-carboxylic acid belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review very few articles have been published on 7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalene-1-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042211302D          

 34 35  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042211302D          

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 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 10 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
M  END
> <DATABASE_ID>
NP0192330

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC(C)C=C(C)C(=O)OC1CCC(C(O)=O)C2(C)CC(C(=C)C(OC)OC)C(=O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O7/c1-8-9-10-16(2)13-17(3)25(31)34-23-12-11-20(24(29)30)27(5)15-19(22(28)14-21(23)27)18(4)26(32-6)33-7/h13-14,16,19-20,23,26H,4,8-12,15H2,1-3,5-7H3,(H,29,30)

> <INCHI_KEY>
VEUYHTJQTVNYEG-UHFFFAOYSA-N

> <FORMULA>
C27H40O7

> <MOLECULAR_WEIGHT>
476.61

> <EXACT_MASS>
476.277403628

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.49618358212865

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

> <JCHEM_LOGP>
5.580207244666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.970458472983456

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.252591152863674

> <JCHEM_PKA_STRONGEST_BASIC>
-4.01702632767847

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
130.3926

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0     -18.672  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -17.338  11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -17.338  13.090   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0     -18.672  13.860   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0     -18.672  15.400   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0     -16.004  13.860   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0     -16.004  15.400   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -16.004  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -16.004   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -14.670   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -16.004   7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -13.337   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -13.337  10.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -14.670  11.550   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -14.670  13.090   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0     -12.003   8.470   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -10.669   9.240   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -9.336   6.930   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.000   9.240   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -12.003   6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -13.337   6.160   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -14.670   6.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -16.004   6.160   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -17.338   6.930   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0     -16.004   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6                                                            
CONECT    8    2    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   31                                             
CONECT   11   10                                                            
CONECT   12   10   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14                                                            
CONECT   16   12   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   16   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   10   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Value	Source
7-(3,3-Dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalene-1-carboxylate	Generator

Chemical Formula

C₂₇H₄₀O₇

Average Mass

476.6100 Da

Monoisotopic Mass

476.27740 Da

IUPAC Name

7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

Traditional Name

7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCC(C)C=C(C)C(=O)OC1CCC(C(O)=O)C2(C)CC(C(=C)C(OC)OC)C(=O)C=C12

InChI Identifier

InChI=1S/C27H40O7/c1-8-9-10-16(2)13-17(3)25(31)34-23-12-11-20(24(29)30)27(5)15-19(22(28)14-21(23)27)18(4)26(32-6)33-7/h13-14,16,19-20,23,26H,4,8-12,15H2,1-3,5-7H3,(H,29,30)

InChI Key

VEUYHTJQTVNYEG-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 eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Cyclohexenone
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Ketone
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	5.58	ChemAxon
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	130.39 m³·mol⁻¹	ChemAxon
Polarizability	53.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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

162816243

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid (NP0192330)

MOL for NP0192330 (7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

3D MOL for NP0192330 (7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

3D SDF for NP0192330 (7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

3D-SDF for NP0192330 (7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

PDB for NP0192330 (7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

3D PDB for NP0192330 (7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

SMILES for NP0192330 (7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

INCHI for NP0192330 (7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

Structure for NP0192330 (7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)

3D Structure for NP0192330 (7-(3,3-dimethoxyprop-1-en-2-yl)-4-[(2,4-dimethyloct-2-enoyl)oxy]-8a-methyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid)