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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:25 UTC
Update Date2022-03-07 02:49:17 UTC
HMDB IDHMDB0003000
Secondary Accession Numbers
  • HMDB03000
Metabolite Identification
Common NameLycopene
DescriptionLycopene (molecular formula: C40H56) is a bright red carotenoid pigment. It is a phytochemical found in tomatoes and other red fruits. Lycopene is the most common carotenoid in the human body and is one of the most potent carotenoid antioxidants. Its name is derived from the tomato's species classification, Solanum lycopersicum. Lycopene is a terpene assembled from 8 isoprene units. Lycopene is the most powerful carotenoid quencher of singlet oxygen. Singlet oxygen from ultraviolet light is a primary cause of skin aging (Wikipedia ).
Structure
Thumb
Synonyms
ValueSource
(6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-Octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaeneChEBI
all-trans-LycopeneChEBI
all trans LycopeneMeSH
LYC O matoMeSH
Pro-lycopeneMeSH
LYCOMATOMeSH
Pro lycopeneMeSH
(6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-Octamethyl-2,6,8,10,12,14,16,18,20,22,24,26,30-dotriacontatridecaeneHMDB
(all-e)-2,6,10,14,19,23,27,31-Octamethyl-2,6,8,10,12,14,16,18,20,22,24,26,30-dotriacontatridecaeneHMDB
trans-LycopeneHMDB
(all-E)-LycopeneHMDB
LycopeneHMDB
psi,psi-CaroteneHMDB
ψ,ψ-CaroteneHMDB
Chemical FormulaC40H56
Average Molecular Weight536.888
Monoisotopic Molecular Weight536.438201803
IUPAC Name(6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene
Traditional Namelycopene
CAS Registry Number502-65-8
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\C=C(/C)CCC=C(C)C
InChI Identifier
InChI=1S/C40H56/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15-22,25-32H,13-14,23-24H2,1-10H3/b12-11+,25-15+,26-16+,31-17+,32-18+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+
InChI KeyOAIJSZIZWZSQBC-GYZMGTAESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentCarotenes
Alternative Parents
Substituents
  • Carotene
  • Branched unsaturated hydrocarbon
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Acyclic olefin
  • Hydrocarbon
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point175 °CNot Available
Boiling Point660.90 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.0e-13 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP15.190 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Breast Milk
Tissue Locations
  • Adipose Tissue
  • Adrenal Gland
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Leukocyte
  • Liver
  • Pancreas
  • Platelet
  • Prostate
  • Spleen
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.444 +/- 0.420 uMAdult (>18 years old)Not Specified
Obese
details
BloodDetected and Quantified0.608 +/- 0.690 uMAdult (>18 years old)Not Specified
Overweight
details
BloodDetected and Quantified0.009 (0.008-0.01) uMAdult (>18 years old)FemaleEndometrial cancer details
BloodDetected and Quantified0.560 +/- 0.290 uMAdult (>18 years old)BothType I diabetes details
BloodDetected and Quantified0.380 +/- 0.220 uMChildren (1 - 13 years old)Not SpecifiedObese details
BloodDetected and Quantified0.450 +/- 0.270 uMChildren (1 - 13 years old)Not SpecifiedOverweight details
Associated Disorders and Diseases
Disease References
Endometrial cancer
  1. Jeong NH, Song ES, Lee JM, Lee KB, Kim MK, Yun YM, Lee JK, Son SK, Lee JP, Kim JH, Hur SY, Kwon YI: Preoperative levels of plasma micronutrients are related to endometrial cancer risk. Acta Obstet Gynecol Scand. 2009;88(4):434-9. doi: 10.1080/00016340902767187. [PubMed:19235557 ]
Obesity
  1. Vioque J, Weinbrenner T, Asensio L, Castello A, Young IS, Fletcher A: Plasma concentrations of carotenoids and vitamin C are better correlated with dietary intake in normal weight than overweight and obese elderly subjects. Br J Nutr. 2007 May;97(5):977-86. [PubMed:17408529 ]
  2. Burrows TL, Warren JM, Colyvas K, Garg ML, Collins CE: Validation of overweight children's fruit and vegetable intake using plasma carotenoids. Obesity (Silver Spring). 2009 Jan;17(1):162-8. doi: 10.1038/oby.2008.495. Epub 2008 Nov 6. [PubMed:18997681 ]
Diabetes mellitus type 1
  1. Granado-Lorencio F, Olmedilla-Alonso B, Blanco-Navarro I, Botella-Romero F, Simal-Anton A: Assessment of carotenoid status and the relation to glycaemic control in type I diabetics: a follow-up study. Eur J Clin Nutr. 2006 Aug;60(8):1000-8. Epub 2006 Feb 1. [PubMed:16452910 ]
Associated OMIM IDs
DrugBank IDDB11231
Phenol Explorer Compound IDNot Available
FooDB IDFDB014534
KNApSAcK IDC00000911
Chemspider ID394156
KEGG Compound IDC05432
BioCyc IDCPD1F-114
BiGG IDNot Available
Wikipedia LinkLycopene
METLIN IDNot Available
PubChem Compound446925
PDB IDNot Available
ChEBI ID15948
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000408
Good Scents IDrw1030761
References
Synthesis ReferenceIto, Shuichi; Yamaguchi, Yuzo. Fermentative production of lycopene. Jpn. Tokkyo Koho (1973), 5 pp.
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Asymmetrically cleaves beta-carotene at the 9',10' double bond resulting in the formation of beta-apo-10'-carotenal and beta-ionone. Besides beta-carotene, lycopene is also oxidatively cleaved. The apocarotenals formed by this enzyme may be the precursors for the biosynthesis of retinoic acid or exert unknown physiological effects.
Gene Name:
BCO2
Uniprot ID:
Q9BYV7
Molecular weight:
61509.65