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Record Information
Version4.0
Creation Date2006-05-22 15:12:25 UTC
Update Date2017-09-27 08:24:18 UTC
HMDB IDHMDB0003000
Secondary Accession Numbers
  • HMDB03000
Metabolite Identification
Common NameLycopene
DescriptionLycopene (molecular formula: C40H56) is a bright red carotenoid pigment, 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. -- Wikipedia; Lycopene is a terpene assembled from 8 isoprene units. -- Wikipedia; 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
(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
lyco VitHMDB
Lycopene 7HMDB
trans-LycopeneHMDB
Lycopene, (cis)-isomerMeSH
Lycopene, (7-cis,7'-cis,9-cis,9'-cis)-isomerMeSH
ProlycopeneMeSH
LYC-O-matoMeSH
Lycopene, (13-cis)-isomerMeSH
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
DescriptionThis compound 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 effect

Health effect:

  Health condition:

    Cancer:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Organ and components:

    Endocrine gland:

  Cell and elements:

    Cell:

    Element:

Source:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Industrial application:

  Pharmaceutical industry:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point175 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0004 g/LALOGPS
logP9.16ALOGPS
logP11.93ChemAxon
logS-6.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity197.81 m³·mol⁻¹ChemAxon
Polarizability73.69 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Breast Milk
Tissue Location
  • Adipose Tissue
  • Adrenal Gland
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Lymphocyte
  • Pancreas
  • Platelet
  • Prostate
  • Skin
  • Spleen
  • Stratum Corneum
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.743 +/- 0.168 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.6 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.61 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.402 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.656 +/- 0.0100 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.360 +/- 0.240 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.400 +/- 0.280 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.420 +/- 0.280 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.420 +/- 0.320 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.330 +/- 0.230 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.350 +/- 0.250 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.610 +/- 0.360 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.703 +/- 0.860 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.440 +/- 0.280 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.474 +/- 0.560 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.510 +/- 0.340 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.640 +/- 0.380 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.926 +/- 0.270 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.374 +/- 0.139 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.248 +/- 0.121 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.394 +/- 0.202 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.266 +/- 0.127 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.640 +/- 0.260 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.660 +/- 0.270 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.577 +/- 0.322 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.260 +/- 0.110 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.280 +/- 0.110 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.61 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.67 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified580 +/- 240 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.574 +/- 0.264 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.600 +/- 0.360 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.580 +/- 0.310 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.696 +/- 0.342 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.57 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.59 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.392 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.509 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.707 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.87 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.64 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.68 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.76 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0705 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.143 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.263 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.406 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.567 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.623 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.170 +/- 0.120 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.335 +/- 0.164 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.01 (0.008-0.014) uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.576 +/- 0.309 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.630 +/- 0.280 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.695 +/- 0.274 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.340 +/- 0.750 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.560 +/- 0.640 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.169 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.177 uMChildren (1-13 years old)FemaleNormal details
BloodDetected and Quantified0.51 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.71 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.771 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1.24 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.320 +/- 0.120 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.434 +/- 0.186 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.527 +/- 0.237 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.531 +/- 0.237 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.563 +/- 0.231 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.585 +/- 0.338 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.590 +/- 0.220 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.631 +/- 0.371 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.658 +/- 0.341 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.760 +/- 0.320 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified759.376 +/- 318.688 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified242.136 +/- 111.755 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.159 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.187 uMChildren (1-13 years old)MaleNormal details
BloodDetected and Quantified0.5 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.74 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified1.44 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.501 +/- 0.338 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.505 +/- 0.183 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.579 +/- 0.253 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.610 +/- 0.240 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.620 +/- 0.308 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.622 +/- 0.320 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.630 +/- 0.276 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.746 +/- 0.379 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.820 +/- 0.380 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified1060 +/- 410 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified817.675 +/- 375.684 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified930 +/- 350 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified204.884 +/- 93.129 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.730 +/- 0.400 uMChildren (1 - 13 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.34 +/- 0.12 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.52 +/- 0.17 uMAdult (>18 years old)BothNormal details
Breast MilkDetected but not Quantified Adult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB015833
KNApSAcK IDC00000911
Chemspider ID394156
KEGG Compound IDC05432
BioCyc IDCPD1F-114
BiGG IDNot Available
Wikipedia LinkLycopene
METLIN ID429
PubChem Compound446925
PDB IDLYC
ChEBI ID15948
References
Synthesis ReferenceIto, Shuichi; Yamaguchi, Yuzo. Fermentative production of lycopene. Jpn. Tokkyo Koho (1973), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Stahl W, Schwarz W, Sundquist AR, Sies H: cis-trans isomers of lycopene and beta-carotene in human serum and tissues. Arch Biochem Biophys. 1992 Apr;294(1):173-7. [PubMed:1550343 ]
  2. Aust O, Stahl W, Sies H, Tronnier H, Heinrich U: Supplementation with tomato-based products increases lycopene, phytofluene, and phytoene levels in human serum and protects against UV-light-induced erythema. Int J Vitam Nutr Res. 2005 Jan;75(1):54-60. [PubMed:15830922 ]
  3. Sengupta A, Das S: The anti-carcinogenic role of lycopene, abundantly present in tomato. Eur J Cancer Prev. 1999 Aug;8(4):325-30. [PubMed:10493308 ]
  4. Porrini M, Riso P: Lymphocyte lycopene concentration and DNA protection from oxidative damage is increased in women after a short period of tomato consumption. J Nutr. 2000 Feb;130(2):189-92. [PubMed:10720168 ]
  5. Bohm V, Bitsch R: Intestinal absorption of lycopene from different matrices and interactions to other carotenoids, the lipid status, and the antioxidant capacity of human plasma. Eur J Nutr. 1999 Jun;38(3):118-25. [PubMed:10443333 ]
  6. Stahl W, von Laar J, Martin HD, Emmerich T, Sies H: Stimulation of gap junctional communication: comparison of acyclo-retinoic acid and lycopene. Arch Biochem Biophys. 2000 Jan 1;373(1):271-4. [PubMed:10620348 ]
  7. Kravchenko LV, Morozov SV, Beketova NA, Deryagina VP, Avren'eva LI, Tutel'yan VA: Antioxidant status of rats receiving lycopene in different doses. Bull Exp Biol Med. 2003 Apr;135(4):353-7. [PubMed:12910307 ]
  8. Zaripheh S, Nara TY, Nakamura MT, Erdman JW Jr: Dietary lycopene downregulates carotenoid 15,15'-monooxygenase and PPAR-gamma in selected rat tissues. J Nutr. 2006 Apr;136(4):932-8. [PubMed:16549453 ]
  9. Hsiao G, Wang Y, Tzu NH, Fong TH, Shen MY, Lin KH, Chou DS, Sheu JR: Inhibitory effects of lycopene on in vitro platelet activation and in vivo prevention of thrombus formation. J Lab Clin Med. 2005 Oct;146(4):216-26. [PubMed:16194683 ]
  10. Gerster H: The potential role of lycopene for human health. J Am Coll Nutr. 1997 Apr;16(2):109-26. [PubMed:9100211 ]
  11. Stahl W, Sies H: Carotenoids and protection against solar UV radiation. Skin Pharmacol Appl Skin Physiol. 2002 Sep-Oct;15(5):291-6. [PubMed:12239422 ]
  12. Ermakov IV, Ermakova MR, Gellermann W, Lademann J: Noninvasive selective detection of lycopene and beta-carotene in human skin using Raman spectroscopy. J Biomed Opt. 2004 Mar-Apr;9(2):332-8. [PubMed:15065899 ]
  13. Walfisch Y, Walfisch S, Agbaria R, Levy J, Sharoni Y: Lycopene in serum, skin and adipose tissues after tomato-oleoresin supplementation in patients undergoing haemorrhoidectomy or peri-anal fistulotomy. Br J Nutr. 2003 Oct;90(4):759-66. [PubMed:13129444 ]
  14. Ribaya-Mercado JD, Garmyn M, Gilchrest BA, Russell RM: Skin lycopene is destroyed preferentially over beta-carotene during ultraviolet irradiation in humans. J Nutr. 1995 Jul;125(7):1854-9. [PubMed:7616301 ]
  15. Yeh S, Hu M: Antioxidant and pro-oxidant effects of lycopene in comparison with beta-carotene on oxidant-induced damage in Hs68 cells. J Nutr Biochem. 2000 Nov;11(11-12):548-554. [PubMed:11137891 ]
  16. Riso P, Visioli F, Erba D, Testolin G, Porrini M: Lycopene and vitamin C concentrations increase in plasma and lymphocytes after tomato intake. Effects on cellular antioxidant protection. Eur J Clin Nutr. 2004 Oct;58(10):1350-8. [PubMed:15054415 ]
  17. Arab L, Steck S: Lycopene and cardiovascular disease. Am J Clin Nutr. 2000 Jun;71(6 Suppl):1691S-5S; discussion 1696S-7S. [PubMed:10837319 ]
  18. Michael McClain R, Bausch J: Summary of safety studies conducted with synthetic lycopene. Regul Toxicol Pharmacol. 2003 Apr;37(2):274-85. [PubMed:12726756 ]

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