ChemFOnt: Showing chemical card for (E)-alpha-Bergamotene (CFc000281765)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:29 UTC

Chemfont ID

CFc000281765

Molecule Identification

Common Name

(E)-alpha-Bergamotene

Definition

≈í¬±-cis-bergamotene belongs to the class of organic compounds known as bicyclic sesquiterpenoids. These are sesquiterpenoids containing exactly two rings, which are fused together. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpene as it is synthesized via isoprene units. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. There are four known Bergamotene isomers including ≈í¬±-cis-, ≈í¬±-trans-, ≈í‚â§-cis- and ≈í‚â§-trans-bergamotene. ≈í¬±-cis-Bergamotene is found in the oils of carrot, bergamot, lime, citron, cottonseed, and kumquat. Isomers of bergamotene have a function as pheromones for some insect species. Evidence suggests that plants under attack by herbivore insects are able to release specific amounts of bergamotene to attract natural enemies of the herbivores, using these sesquiterpenes as a defense mechanism (PMID: 16418295 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-a-Bergamotene	Generator
(e)-Α-bergamotene	Generator

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.3511

Monoisotopic Molecular Weight

204.187800768

IUPAC Name

(1R,5R,6S)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene

Traditional Name

(1R,5R,6S)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene

CAS Registry Number

None

SMILES

CC(C)=CCC[C@@]1(C)[C@H]2C[C@@H]1C(C)=CC2

InChI Identifier

InChI=1S/C15H24/c1-11(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6-7,13-14H,5,8-10H2,1-4H3/t13-,14-,15+/m1/s1

InChI Key

YMBFCQPIMVLNIU-KFWWJZLASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Pinane monoterpenoid
Bicyclic monoterpenoid
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

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302249)

Lime (FooDB: FOOD00053)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0068 g/L	ALOGPS
logP	5.91	ALOGPS
logP	4.46	ChemAxon
logS	-4.5	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.52 m³·mol⁻¹	ChemAxon
Polarizability	26.58 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

HMDB0302249

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003887

KNApSAcK ID

Not Available

Chemspider ID

10250932

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13889654

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (E)-alpha-Bergamotene (CFc000281765)

MOL for CFc000281765 ((E)-alpha-Bergamotene)

3D MOL for CFc000281765 ((E)-alpha-Bergamotene)

3D SDF for CFc000281765 ((E)-alpha-Bergamotene)

3D-SDF for CFc000281765 ((E)-alpha-Bergamotene)

PDB for CFc000281765 ((E)-alpha-Bergamotene)

3D PDB for CFc000281765 ((E)-alpha-Bergamotene)

SMILES for CFc000281765 ((E)-alpha-Bergamotene)

INCHI for CFc000281765 ((E)-alpha-Bergamotene)

Structure for CFc000281765 ((E)-alpha-Bergamotene)

3D Structure for CFc000281765 ((E)-alpha-Bergamotene)