NP-MRD: Showing NP-Card for 6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-octahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate (NP0212358)

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Record Information

Version

2.0

Created at

2022-09-05 11:00:10 UTC

Updated at

2022-09-05 11:00:10 UTC

NP-MRD ID

NP0212358

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-octahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate

Description

6-Hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-decahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate 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. 6-Hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-decahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231521152D          

 32 33  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004231521152D          

 32 33  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0212358

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC=CC(C)=CC=CC(=O)OC1CCC2C(=O)C(O)C(CC2(C)C1C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O4/c1-7-8-9-10-11-13-20(4)14-12-15-25(29)32-24-17-16-23-27(31)26(30)22(19(2)3)18-28(23,6)21(24)5/h11-15,21-24,26,30H,2,7-10,16-18H2,1,3-6H3

> <INCHI_KEY>
GRKMYOFGMGYHPG-UHFFFAOYSA-N

> <FORMULA>
C28H42O4

> <MOLECULAR_WEIGHT>
442.64

> <EXACT_MASS>
442.308309832

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.082063479665834

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-decahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate

> <ALOGPS_LOGP>
6.41

> <JCHEM_LOGP>
6.793215365666667

> <ALOGPS_LOGS>
-6.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.691601604077817

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.091432093989233

> <JCHEM_PKA_STRONGEST_BASIC>
-3.633607385006889

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
133.0733

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.50e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-octahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate

> <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  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.672 -12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.005 -11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.339 -12.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.673 -11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.006 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.340 -11.550   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      26.674 -12.320   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      25.340 -10.010   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      26.674  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.674  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.007  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.341  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.675  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      30.675  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      32.008  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      33.342  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      32.008  -9.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      30.675 -10.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      29.341  -9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.341 -10.780   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      28.007 -10.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      28.007 -11.550   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      33.342 -10.010   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      33.342 -11.550   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      34.676  -9.240   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.005 -10.010   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   32                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   27                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   18   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   15   28                                                  
CONECT   28   27                                                            
CONECT   29   23   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    8                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Value	Source
6-Hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-decahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoic acid	Generator

Chemical Formula

C₂₈H₄₂O₄

Average Mass

442.6400 Da

Monoisotopic Mass

442.30831 Da

IUPAC Name

6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-decahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate

Traditional Name

6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-octahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate

CAS Registry Number

Not Available

SMILES

CCCCCC=CC(C)=CC=CC(=O)OC1CCC2C(=O)C(O)C(CC2(C)C1C)C(C)=C

InChI Identifier

InChI=1S/C28H42O4/c1-7-8-9-10-11-13-20(4)14-12-15-25(29)32-24-17-16-23-27(31)26(30)22(19(2)3)18-28(23,6)21(24)5/h11-15,21-24,26,30H,2,7-10,16-18H2,1,3-6H3

InChI Key

GRKMYOFGMGYHPG-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
Fatty acid ester
Fatty acyl
Cyclic alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
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	6.41	ALOGPS
logP	6.79	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	13.09	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	133.07 m³·mol⁻¹	ChemAxon
Polarizability	53.08 Å³	ChemAxon
Number of Rings	2	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

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 6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-octahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate (NP0212358)

MOL for NP0212358 (6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-octahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate)

3D MOL for NP0212358 (6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-octahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate)

3D SDF for NP0212358 (6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-octahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate)

3D-SDF for NP0212358 (6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-octahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate)

PDB for NP0212358 (6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-octahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate)

3D PDB for NP0212358 (6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-octahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate)

SMILES for NP0212358 (6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-octahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate)

INCHI for NP0212358 (6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-octahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate)

Structure for NP0212358 (6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-octahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate)

3D Structure for NP0212358 (6-hydroxy-1,8a-dimethyl-5-oxo-7-(prop-1-en-2-yl)-octahydronaphthalen-2-yl 5-methyldodeca-2,4,6-trienoate)