CHEBI:27740 - γ-carotene

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ChEBI Name γ-carotene
ChEBI ID CHEBI:27740
ChEBI ASCII Name gamma-carotene
Definition A cyclic carotene obtained by the cyclisation of lycopene.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:24189, CHEBI:10560
Supplier Information ZINC000008219952
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γ-Carotene (gamma-carotene) is a carotenoid, and is a biosynthetic intermediate for cyclized carotenoid synthesis in plants. It is formed from cyclization of lycopene by lycopene cyclase epsilon. Along with several other carotenoids, γ-carotene is a vitamer of vitamin A in herbivores and omnivores. Carotenoids with a cyclized, beta-ionone ring can be converted to vitamin A, also known as retinol, by the enzyme beta-carotene 15,15'-dioxygenase; however, the bioconversion of γ-carotene to retinol has not been well-characterized. γ-Carotene has tentatively been identified as a biomarker for green and purple sulfur bacteria in a sample from the 1.640 ± 0.003-Gyr-old Barney Creek Formation in Northern Australia which comprises marine sediments. Tentative discovery of γ-carotene in marine sediments implies a past euxinic environment, where water columns were anoxic and sulfidic. This is significant for reconstructing past oceanic conditions, but so far γ-carotene has only been potentially identified in the one measured sample.
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Formula C40H56
Net Charge 0
Average Mass 536.87264
Monoisotopic Mass 536.43820
InChI InChI=1S/C40H56/c1-32(2)18-13-21-35(5)24-15-26-36(6)25-14-22-33(3)19-11-12-20-34(4)23-16-27-37(7)29-30-39-38(8)28-17-31-40(39,9)10/h11-12,14-16,18-20,22-27,29-30H,13,17,21,28,31H2,1-10H3/b12-11+,22-14+,23-16+,26-15+,30-29+,33-19+,34-20+,35-24+,36-25+,37-27+
InChIKey HRQKOYFGHJYEFS-BXOLYSJBSA-N
SMILES CC(C)=CCC\C(C)=C\C=C\C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C
Roles Classification
Biological Role(s): fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing γ-carotene (CHEBI:27740) has role fungal metabolite (CHEBI:76946)
γ-carotene (CHEBI:27740) has role plant metabolite (CHEBI:76924)
γ-carotene (CHEBI:27740) is a carotenoid β-end derivative (CHEBI:139120)
γ-carotene (CHEBI:27740) is a cyclic carotene (CHEBI:35163)
Incoming 1'-hydroxy-γ-carotene (CHEBI:80133) has parent hydride γ-carotene (CHEBI:27740)
rubixanthin (CHEBI:8907) has parent hydride γ-carotene (CHEBI:27740)
IUPAC Name
β,ψ-carotene
Synonyms Sources
gamma-Carotene KEGG COMPOUND
γ-carotene UniProt
Manual Xrefs Databases
C00000926 KNApSAcK
C05435 KEGG COMPOUND
CPD1F-126 MetaCyc
Gamma-carotene Wikipedia
LMPR01070260 LIPID MAPS
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Registry Numbers Types Sources
2066713 Reaxys Registry Number Reaxys
472-93-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
05 February 2019