NP-MRD: Showing NP-Card for 3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one (NP0238004)

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Record Information

Version

2.0

Created at

2022-09-06 21:18:52 UTC

Updated at

2022-09-06 21:18:52 UTC

NP-MRD ID

NP0238004

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one

Description

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. 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, 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. 3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one is found in Hypericum perforatum and Hypericum yezoense. This could make 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.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241211122D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02241211122D          

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M  END
> <DATABASE_ID>
NP0238004

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)C1C(=O)C(CC=C(C)C)CC(CC=C(C)C)C1(C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O2/c1-18(2)11-10-16-27(9)23(15-13-20(5)6)17-22(14-12-19(3)4)26(29)24(27)25(28)21(7)8/h11-13,21-24H,10,14-17H2,1-9H3

> <INCHI_KEY>
AXAAMKAGJNUYDB-UHFFFAOYSA-N

> <FORMULA>
C27H44O2

> <MOLECULAR_WEIGHT>
400.6371

> <EXACT_MASS>
400.334130652

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
50.26190248160182

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one

> <ALOGPS_LOGP>
6.84

> <JCHEM_LOGP>
8.303097876

> <ALOGPS_LOGS>
-5.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.747739459628493

> <JCHEM_PKA_STRONGEST_BASIC>
-7.326665462192693

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
127.6442

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.53e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

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   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.663   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.668   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.998   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.998   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.668   3.077   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.333   3.077   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.002   3.077   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.668   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.333   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.668   4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.998   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.333   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.668   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.002   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.668   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.668  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.663  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.663  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.998  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.668  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.998  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.333   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.333  -1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.668  -3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.002  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.333  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   23   24                                             
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   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    3   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    4                                                            
CONECT   24    4   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₄O₂

Average Mass

400.6371 Da

Monoisotopic Mass

400.33413 Da

IUPAC Name

3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one

Traditional Name

3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)C1C(=O)C(CC=C(C)C)CC(CC=C(C)C)C1(C)CCC=C(C)C

InChI Identifier

InChI=1S/C27H44O2/c1-18(2)11-10-16-27(9)23(15-13-20(5)6)17-22(14-12-19(3)4)26(29)24(27)25(28)21(7)8/h11-13,21-24H,10,14-17H2,1-9H3

InChI Key

AXAAMKAGJNUYDB-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
Hypericum yezoense	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
1,3-diketone
1,3-dicarbonyl compound
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	6.84	ALOGPS
logP	8.3	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	10.75	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	127.64 m³·mol⁻¹	ChemAxon
Polarizability	50.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036012

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014828

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

73808498

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one (NP0238004)

MOL for NP0238004 (3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one)

3D MOL for NP0238004 (3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one)

3D SDF for NP0238004 (3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one)

3D-SDF for NP0238004 (3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one)

PDB for NP0238004 (3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one)

3D PDB for NP0238004 (3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one)

SMILES for NP0238004 (3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one)

INCHI for NP0238004 (3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one)

Structure for NP0238004 (3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one)

3D Structure for NP0238004 (3-methyl-4,6-bis(3-methylbut-2-en-1-yl)-3-(4-methylpent-3-en-1-yl)-2-(2-methylpropanoyl)cyclohexan-1-one)