NP-MRD: Showing NP-Card for Bicycloelemene (NP0049043)

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Record Information

Version

2.0

Created at

2022-03-17 21:06:13 UTC

Updated at

2022-03-17 21:06:13 UTC

NP-MRD ID

NP0049043

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bicycloelemene

Description

Bicycloelemene belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. Bicycloelemene is possibly neutral. Outside of the human body, Bicycloelemene has been detected, but not quantified in, a few different foods, such as herbs and spices, peppermints, and spearmints. Bicycloelemene is found in Conocephalum conicum, Litsea cubeba , Murraya paniculata , peppermint oil, Piper nigrum , Polygonum minus, Satureja subspicata , Valeriana officinalis and Xylopia sericea . This could make bicycloelemene a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310162D          

 15 16  0  0  0  0            999 V2000
    2.9999    2.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    0.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7177    1.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1874    2.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  2  0  0  0  0
  9  8  1  0  0  0  0
 10  2  2  0  0  0  0
 10  3  1  0  0  0  0
 11  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  4  1  0  0  0  0
 14  5  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049043

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1C2C(CCC1(C)C=C)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-7-15(6)9-8-11-13(14(11,4)5)12(15)10(2)3/h7,11-13H,1-2,8-9H2,3-6H3

> <INCHI_KEY>
LKQMMFFQYMYQOJ-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
25.797416072904326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-ethenyl-3,7,7-trimethyl-2-(prop-1-en-2-yl)bicyclo[4.1.0]heptane

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
4.318829772999999

> <ALOGPS_LOGS>
-5.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
66.4682

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-ethenyl-3,7,7-trimethyl-2-(prop-1-en-2-yl)bicyclo[4.1.0]heptane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.600   4.795   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.557   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.889   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.435   3.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.435   1.130   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.073   2.813   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.083   4.527   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.223   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.557   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.223   5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.889   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.223   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.889   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.445   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.557   3.080   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4   14                                                            
CONECT    5   14                                                            
CONECT    6   15                                                            
CONECT    7    1   15                                                       
CONECT    8    9   11                                                       
CONECT    9    8   15                                                       
CONECT   10    2    3   12                                                  
CONECT   11    8   13   14                                                  
CONECT   12   10   13   15                                                  
CONECT   13   11   12   14                                                  
CONECT   14    4    5   11   13                                             
CONECT   15    6    7    9   12                                             
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
(-)-Bicycloelemene	HMDB
2-Isopropenyl-3-methyl-3-vinylbicyclo[4.1.0]heptane	HMDB
3-Ethenyl-3,7,7-trimethyl-2-(1-methylethenyl)bicyclo[4.1.0]heptane, 9ci	HMDB

Chemical Formula

C₁₅H₂₄

Average Mass

204.3511 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

3-ethenyl-3,7,7-trimethyl-2-(prop-1-en-2-yl)bicyclo[4.1.0]heptane

Traditional Name

3-ethenyl-3,7,7-trimethyl-2-(prop-1-en-2-yl)bicyclo[4.1.0]heptane

CAS Registry Number

32531-56-9

SMILES

CC(=C)C1C2C(CCC1(C)C=C)C2(C)C

InChI Identifier

InChI=1S/C15H24/c1-7-15(6)9-8-11-13(14(11,4)5)12(15)10(2)3/h7,11-13H,1-2,8-9H2,3-6H3

InChI Key

LKQMMFFQYMYQOJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Conocephalum conicum	LOTUS Database	35616633
Litsea cubeba	Plant	KNApSAcK
Mentha spicata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha x piperita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Murraya paniculata	Plant	KNApSAcK
peppermint oil	-	KNApSAcK
Piper nigrum L.	Plant	KNApSAcK
Polygonum minus	Plant	KNApSAcK
Satureja subspicata	Plant	KNApSAcK
Valeriana officinalis	LOTUS Database	35616633
Xylopia sericea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Elemane sesquiterpenoids

Alternative Parents

Substituents

Elemane sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
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	4.09	ALOGPS
logP	4.32	ChemAxon
logS	-5.2	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.47 m³·mol⁻¹	ChemAxon
Polarizability	25.8 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038166

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017397

KNApSAcK ID

C00011971

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

76419358

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Bicycloelemene (NP0049043)

MOL for NP0049043 (Bicycloelemene)

3D MOL for NP0049043 (Bicycloelemene)

3D SDF for NP0049043 (Bicycloelemene)

3D-SDF for NP0049043 (Bicycloelemene)

PDB for NP0049043 (Bicycloelemene)

3D PDB for NP0049043 (Bicycloelemene)

SMILES for NP0049043 (Bicycloelemene)

INCHI for NP0049043 (Bicycloelemene)

Structure for NP0049043 (Bicycloelemene)

3D Structure for NP0049043 (Bicycloelemene)