NP-MRD: Showing NP-Card for methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate (NP0164394)

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Record Information

Version

1.0

Created at

2022-09-02 23:15:44 UTC

Updated at

2022-09-02 23:15:44 UTC

NP-MRD ID

NP0164394

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate

Description

2-(Methoxycarbonyl)-5-methyl-2,4-bis(3-methyl-2-butenyl)-6-(2-methyl-1-oxopropyl)-5-(4-methyl-3-pentenyl)cyclohexanone belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. 2-(Methoxycarbonyl)-5-methyl-2,4-bis(3-methyl-2-butenyl)-6-(2-methyl-1-oxopropyl)-5-(4-methyl-3-pentenyl)cyclohexanone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-(Methoxycarbonyl)-5-methyl-2,4-bis(3-methyl-2-butenyl)-6-(2-methyl-1-oxopropyl)-5-(4-methyl-3-pentenyl)cyclohexanone has been detected, but not quantified in, a few different foods, such as alcoholic beverages, herbs and spices, and tea. methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate is found in Hypericum perforatum. It was first documented in 2000 (PMID: 11413487). This could make 2-(methoxycarbonyl)-5-methyl-2,4-bis(3-methyl-2-butenyl)-6-(2-methyl-1-oxopropyl)-5-(4-methyl-3-pentenyl)cyclohexanone a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241220352D          

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M  END

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M  END


  Mrv0541 02241220352D          

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  1  6  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  1  0  0  0  0
  4  5  1  0  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  1  0  0  0  0
  7 11  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 13 31  1  0  0  0  0
 13 32  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0164394

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(CC=C(C)C)CC(CC=C(C)C)C(C)(CCC=C(C)C)C(C(=O)C(C)C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O4/c1-19(2)12-11-16-28(9)23(14-13-20(3)4)18-29(27(32)33-10,17-15-21(5)6)26(31)24(28)25(30)22(7)8/h12-13,15,22-24H,11,14,16-18H2,1-10H3

> <INCHI_KEY>
QVUJYADKXQKJHK-UHFFFAOYSA-N

> <FORMULA>
C29H46O4

> <MOLECULAR_WEIGHT>
458.6731

> <EXACT_MASS>
458.33960996

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
55.2280582288209

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate

> <ALOGPS_LOGP>
6.12

> <JCHEM_LOGP>
8.196698833000001

> <ALOGPS_LOGS>
-5.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.910796124719633

> <JCHEM_PKA_STRONGEST_BASIC>
-6.996007611337291

> <JCHEM_POLAR_SURFACE_AREA>
60.440000000000005

> <JCHEM_REFRACTIVITY>
138.63150000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.94e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.663   1.462   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.663  -0.077   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.668  -0.847   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.997  -0.077   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.997   1.462   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.668   2.229   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.331   2.232   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.665   1.462   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.000   2.232   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.665  -0.077   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.331   3.771   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.668   3.769   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.433   2.796   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.997   0.693   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.331   1.462   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.666   0.693   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.000   1.462   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.666  -0.847   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.668  -2.386   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.666  -3.156   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.666  -4.695   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.000  -5.464   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.668  -5.464   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.997  -1.616   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.331  -0.847   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.331  -2.386   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.665  -3.156   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.665  -4.695   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.000  -5.464   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.331  -5.464   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.663   4.131   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.972   2.796   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.433   5.464   0.000  0.00  0.00           C+0
CONECT    1    2    6   13   14                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5   24   25                                             
CONECT    5    4    6    7                                                  
CONECT    6    1    5   12                                                  
CONECT    7    5    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7                                                            
CONECT   12    6                                                            
CONECT   13    1   31   32                                                  
CONECT   14    1   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    3   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    4                                                            
CONECT   25    4   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   13   33                                                       
CONECT   32   13                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylic acid	Generator

Chemical Formula

C₂₉H₄₆O₄

Average Mass

458.6731 Da

Monoisotopic Mass

458.33961 Da

IUPAC Name

methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate

Traditional Name

methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(CC=C(C)C)CC(CC=C(C)C)C(C)(CCC=C(C)C)C(C(=O)C(C)C)C1=O

InChI Identifier

InChI=1S/C29H46O4/c1-19(2)12-11-16-28(9)23(14-13-20(3)4)18-29(27(32)33-10,17-15-21(5)6)26(31)24(28)25(30)22(7)8/h12-13,15,22-24H,11,14,16-18H2,1-10H3

InChI Key

QVUJYADKXQKJHK-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
Hypericum perforatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monocyclic monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
Fatty acid ester
1,3-diketone
1,3-dicarbonyl compound
Fatty acyl
Methyl ester
Cyclic ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	6.12	ALOGPS
logP	8.2	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	138.63 m³·mol⁻¹	ChemAxon
Polarizability	55.23 Å³	ChemAxon
Number of Rings	1	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

HMDB0035995

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014804

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

73106016

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
LOTUS database [Link]

Showing NP-Card for methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate (NP0164394)

MOL for NP0164394 (methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate)

3D MOL for NP0164394 (methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate)

3D SDF for NP0164394 (methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate)

3D-SDF for NP0164394 (methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate)

PDB for NP0164394 (methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate)

3D PDB for NP0164394 (methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate)

SMILES for NP0164394 (methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate)

INCHI for NP0164394 (methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate)

Structure for NP0164394 (methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate)

3D Structure for NP0164394 (methyl 4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate)