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Human Metabolome Database Version 2.5

 

Showing metabocard for Lycopene (HMDB03000)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-05-22 16:12:25
Update Date 2009-11-22 23:55:48
Accession Number HMDB03000
Secondary Accession Numbers Not Available
Common Name Lycopene
Description Lycopene (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
Synonyms
  1. (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-dotriacontatridecaene
  2. (all-E)-2,6,10,14,19,23,27,31-Octamethyl-2,6,8,10,12,14,16,18,20,22,24,26,30-dotriacontatridecaene
  3. Lyco Vit
  4. Lycopene
  5. Lycopene 7
  6. all-trans-Lycopene
  7. trans-Lycopene
Chemical 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
Chemical Formula C40H56
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Miscellanous
Class
  • Carotenoids
Sub Class
  • Long chain alkenes
Family
  • Plant Metabolite
Species
  • alkene
Biofunction
—
Application
—
Source
  • Exogenous
Average Molecular Weight 536.873
Monoisotopic Molecular Weight 536.438232
Isomeric SMILES CC(C)=CCCC(C)=CC=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC=C(/C)CCC=C(/C)C
Canonical SMILES CC(C)=CCCC(C)=CC=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC=C(C)CCC=C(C)C
KEGG Compound ID C05432 Link Image
BioCyc ID CPD1F-114 Link Image
BiGG ID Not Available
Wikipedia Link Lycopene Link Image
NuGOwiki Link HMDB03000 Link Image
Metagene Link HMDB03000 Link Image
METLIN ID 429 Link Image
PubChem Compound 446925 Link Image
PubChem Substance 10877447 Link Image
ChEBI ID 15948 Link Image
CAS Registry Number 502-65-8
InChI Identifier InChI=1/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+
Synthesis Reference Ito, Shuichi; Yamaguchi, Yuzo. Fermentative production of lycopene. Jpn. Tokkyo Koho (1973), 5 pp.
Melting Point (Experimental) 175 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 9.59e-18 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]; 3.97e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 9.16 [Predicted by ALOGPS]; 10.2 [Predicted by PubChem via XLOGP]; 17.64 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
Biofluid Location
  • Blood
Tissue Location
Tissue References
Adipose Tissue —
Adrenal Gland —
Fibroblasts —
Intestine —
Kidney —
Liver —
Lymphocyte —
Pancreas —
Platelet —
Prostate —
Skin —
Spleen —
Stratum Corneum —
Concentrations (Normal)
Biofluid Blood
Value 0.743 +/- 0.168 uM
Age Adult:>18 yrs old
Sex Female
Patient information Normal
Comments Total plasma lycopene
References
  • Alien CM, Smith AM, Clinton SK, Schwartz SJ: Tomato consumption increases lycopene isomer concentrations in breast milk and plasma of lactating women. J Am Diet Assoc. 2002 Sep;102(9):1257-62. [PubMed Link Image]
Biofluid Blood
Value 0.01 (0.008-0.014) uM
Age Adult:>18 yrs old
Sex Female
Patient information Normal
Comments Not Available
References
  • 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. [PubMed Link Image]
Biofluid Blood
Value 0.34 +/- 0.12 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Porrini M, Riso P, Brusamolino A, Berti C, Guarnieri S, Visioli F: Daily intake of a formulated tomato drink affects carotenoid plasma and lymphocyte concentrations and improves cellular antioxidant protection. Br J Nutr. 2005 Jan;93(1):93-9. [PubMed Link Image]
Concentrations (Abnormal)
Biofluid Blood
Value 0.009 (0.008-0.01) uM
Age Adult:>18 yrs old
Sex Female
Condition Endometrial cancer
Comments Not Available
References
  • 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. [PubMed Link Image]
Biofluid Blood
Value 0.52 +/- 0.17 uM
Age Adult:>18 yrs old
Sex Both
Comments Not Available
References
  • Porrini M, Riso P, Brusamolino A, Berti C, Guarnieri S, Visioli F: Daily intake of a formulated tomato drink affects carotenoid plasma and lymphocyte concentrations and improves cellular antioxidant protection. Br J Nutr. 2005 Jan;93(1):93-9. [PubMed Link Image]
Associated Disorders
Condition References
Endometrial cancer
  • 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. [PubMed Link Image]
OMIM ID
Pathways Not Available
General References
  1. 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 Link Image]
  2. 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 Link Image]
  3. 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 Link Image]
  4. 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 Link Image]
  5. 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 Link Image]
  6. 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 Link Image]
  7. 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 Link Image]
  8. 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 Link Image]
  9. Gerster H: The potential role of lycopene for human health. J Am Coll Nutr. 1997 Apr;16(2):109-26. [PubMed Link Image]
  10. Stahl W, Sies H: Carotenoids and protection against solar UV radiation. Skin Pharmacol Appl Skin Physiol. 2002 Sep-Oct;15(5):291-6. [PubMed Link Image]
  11. 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 Link Image]
  12. 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 Link Image]
  13. 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 Link Image]
  14. 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 Link Image]
  15. 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 Link Image]
  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 Link Image]
  17. Arab L, Steck S: Lycopene and cardiovascular disease. Am J Clin Nutr. 2000 Jun;71(6 Suppl):1691S-5S; discussion 1696S-7S. [PubMed Link Image]
  18. Michael McClain R, Bausch J: Summary of safety studies conducted with synthetic lycopene. Regul Toxicol Pharmacol. 2003 Apr;37(2):274-85. [PubMed Link Image]
  19. Wikipedia Link Image
Metabolic Enzymes
  1. Beta,beta-carotene 9',10'-oxygenase
Enzyme 1 [top]
Enzyme 1 ID 14389
Enzyme 1 Name Beta,beta-carotene 9',10'-oxygenase
Enzyme 1 Synonyms
  1. B-diox-II
  2. Beta-carotene dioxygenase 2
Enzyme 1 Gene Name BCO2
Enzyme 1 Protein Sequence >Beta,beta-carotene 9',10'-oxygenase 
MFFRVFLHFIRSHSATAVDFLPVMVHRLPVFKRYMGNTPQKKAVFGQCRGLPCVAPLLTT
VEEAPRGISARVWGHFPKWLNGSLLRIGPGKFEFGKDKYNHWFDGMALLHQFRMAKGTVT
YRSKFLQSDTYKANSAKNRIVISEFGTLALPDPCKNVFERFMSRFELPGKAAAMTDNTNV
NYVRYKGDYYLCTETNFMNKVDIETLEKTEKVDWSKFIAVNGATAHPHYDLDGTAYNMGN
SFGPYGFSYKVIRVPPEKVDLGETIHGVQVICSIASTEKGKPSYYHSFGMTRNYIIFIEQ
PLKMNLWKIATSKIRGKAFSDGISWEPQCNTRFHVVEKRTGQLLPGRYYSKPFVTFHQIN
AFEDQGCVIIDLCCQDNGRTLEVYQLQNLRKAGEGLDQVHNSAAKSFPRRFVLPLNVSLN
APEGDNLSPLSYTSASAVKQADGTIWCSHENLHQEDLEKEGGIEFPQIYYDRFSGKKYHF
FYGCGFRHLVGDSLIKVDVVNKTLKVWREDGFYPSEPVFVPAPGTNEEDGGVILSVVITP
NQNESNFILVLDAKNFEELGRAEVPVQMPYGFHGTFIPI
Enzyme 1 Number of Residues 579
Enzyme 1 Molecular Weight 65673.7
Enzyme 1 Theoretical pI 8.55
Enzyme 1 GO Classification Not Available
Enzyme 1 General Function Secondary metabolites biosynthesis, transport and catabolism
Enzyme 1 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
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 82617624 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q9BYV7 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name BCDO2_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1740 bp 
ATGTTTTTTCGAGTCTTTCTCCATTTTATCAGGAGTCATTCTGCCACTGCAGTGGATTTC
CTTCCTGTGATGGTGCACCGGCTCCCAGTTTTCAAAAGGTACATGGGAAATACTCCTCAG
AAAAAAGCCGTCTTTGGGCAGTGTCGGGGTCTGCCATGTGTTGCACCGCTGCTGACCACA
GTGGAAGAGGCTCCACGGGGCATCTCTGCTCGAGTCTGGGGACATTTTCCTAAGTGGCTC
AATGGCTCTCTACTTCGAATTGGACCTGGGAAATTCGAGTTTGGGAAGGATAAGTACAAT
CATTGGTTTGATGGGATGGCGCTGCTTCACCAGTTCAGAATGGCAAAGGGCACAGTGACA
TACAGGAGCAAGTTTCTACAGAGTGATACATATAAGGCCAACAGTGCTAAAAACCGAATT
GTGATCTCAGAATTTGGCACACTGGCTCTCCCGGATCCATGCAAGAATGTTTTTGAACGT
TTCATGTCCAGGTTTGAGCTGCCTGGTAAAGCTGCAGCCATGACTGACAATACTAATGTC
AACTATGTGCGGTACAAGGGTGATTACTACCTCTGCACTGAGACCAACTTTATGAATAAA
GTGGACATTGAAACTCTGGAAAAAACAGAAAAGGTAGATTGGAGCAAATTTATTGCTGTG
AATGGAGCAACTGCACATCCTCATTATGACCTGGATGGAACAGCATACAATATGGGGAAC
TCCTTTGGGCCATATGGTTTCTCCTATAAGGTTATTCGGGTTCCTCCAGAGAAGGTGGAC
CTTGGGGAGACAATCCATGGAGTCCAGGTGATATGTTCTATTGCTTCTACAGAGAAAGGG
AAACCTTCTTACTACCATAGCTTTGGAATGACAAGGAACTATATAATTTTCATTGAACAA
CCTCTAAAGATGAACCTGTGGAAAATTGCCACTTCTAAAATTCGGGGAAAGGCCTTTTCA
GATGGGATAAGCTGGGAACCCCAGTGTAATACGCGGTTTCATGTGGTGGAAAAACGCACT
GGACAGCTCCTTCCAGGGAGATACTACAGCAAACCTTTTGTTACATTTCATCAAATCAAT
GCCTTTGAGGACCAGGGCTGTGTTATAATTGATTTGTGCTGTCAAGATAATGGAAGAACC
CTAGAAGTTTACCAGTTACAGAATCTCAGGAAGGCTGGGGAAGGGCTTGATCAGGTCCAT
AATTCAGCAGCCAAATCTTTCCCTCGAAGGTTTGTTTTGCCTTTAAATGTCAGTTTGAAT
GCCCCTGAGGGAGACAACCTGAGTCCATTGTCCTATACTTCAGCCAGTGCTGTGAAACAG
GCTGATGGAACGATCTGGTGCTCTCATGAAAATCTACATCAGGAGGACCTAGAAAAGGAA
GGAGGCATTGAATTTCCTCAGATCTACTATGATCGATTCAGTGGCAAAAAGTATCATTTC
TTTTATGGCTGTGGCTTTCGGCATTTAGTGGGGGATTCTCTGATCAAGGTTGATGTGGTG
AATAAGACACTGAAGGTTTGGAGAGAAGATGGCTTTTATCCCTCAGAACCTGTTTTTGTT
CCAGCACCAGGAACCAATGAAGAAGATGGTGGGGTTATTCTTTCTGTGGTGATCACTCCC
AACCAGAATGAAAGCAATTTTATCCTAGTTTTGGATGCCAAGAACTTTGAAGAGCTGGGC
CGAGCAGAGGTACCTGTGCAGATGCCTTATGGGTTCCATGGTACCTTCATACCCATCTGA
Enzyme 1 GenBank Gene ID NM_031938.4 Link Image
Enzyme 1 GeneCard ID BCO2 Link Image
Enzyme 1 GenAtlas ID BCO2 Link Image
Enzyme 1 HGNC ID HGNC:18503 Link Image
Enzyme 1 Chromosome Location 1
Enzyme 1 Locus 11q22.3-q23.1
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Ota T, Suzuki Y, Nishikawa T, Otsuki T, Sugiyama T, Irie R, Wakamatsu A, Hayashi K, Sato H, Nagai K, Kimura K, Makita H, Sekine M, Obayashi M, Nishi T, Shibahara T, Tanaka T, Ishii S, Yamamoto J, Saito K, Kawai Y, Isono Y, Nakamura Y, Nagahari K, Murakami K, Yasuda T, Iwayanagi T, Wagatsuma M, Shiratori A, Sudo H, Hosoiri T, Kaku Y, Kodaira H, Kondo H, Sugawara M, Takahashi M, Kanda K, Yokoi T, Furuya T, Kikkawa E, Omura Y, Abe K, Kamihara K, Katsuta N, Sato K, Tanikawa M, Yamazaki M, Ninomiya K, Ishibashi T, Yamashita H, Murakawa K, Fujimori K, Tanai H, Kimata M, Watanabe M, Hiraoka S, Chiba Y, Ishida S, Ono Y, Takiguchi S, Watanabe S, Yosida M, Hotuta T, Kusano J, Kanehori K, Takahashi-Fujii A, Hara H, Tanase TO, Nomura Y, Togiya S, Komai F, Hara R, Takeuchi K, Arita M, Imose N, Musashino K, Yuuki H, Oshima A, Sasaki N, Aotsuka S, Yoshikawa Y, Matsunawa H, Ichihara T, Shiohata N, Sano S, Moriya S, Momiyama H, Satoh N, Takami S, Terashima Y, Suzuki O, Nakagawa S, Senoh A, Mizoguchi H, Goto Y, Shimizu F, Wakebe H, Hishigaki H, Watanabe T, Sugiyama A, Takemoto M, Kawakami B, Yamazaki M, Watanabe K, Kumagai A, Itakura S, Fukuzumi Y, Fujimori Y, Komiyama M, Tashiro H, Tanigami A, Fujiwara T, Ono T, Yamada K, Fujii Y, Ozaki K, Hirao M, Ohmori Y, Kawabata A, Hikiji T, Kobatake N, Inagaki H, Ikema Y, Okamoto S, Okitani R, Kawakami T, Noguchi S, Itoh T, Shigeta K, Senba T, Matsumura K, Nakajima Y, Mizuno T, Morinaga M, Sasaki M, Togashi T, Oyama M, Hata H, Watanabe M, Komatsu T, Mizushima-Sugano J, Satoh T, Shirai Y, Takahashi Y, Nakagawa K, Okumura K, Nagase T, Nomura N, Kikuchi H, Masuho Y, Yamashita R, Nakai K, Yada T, Nakamura Y, Ohara O, Isogai T, Sugano S: Complete sequencing and characterization of 21,243 full-length human cDNAs. Nat Genet. 2004 Jan;36(1):40-5. Epub 2003 Dec 21. [PubMed Link Image]
  2. Taylor TD, Noguchi H, Totoki Y, Toyoda A, Kuroki Y, Dewar K, Lloyd C, Itoh T, Takeda T, Kim DW, She X, Barlow KF, Bloom T, Bruford E, Chang JL, Cuomo CA, Eichler E, FitzGerald MG, Jaffe DB, LaButti K, Nicol R, Park HS, Seaman C, Sougnez C, Yang X, Zimmer AR, Zody MC, Birren BW, Nusbaum C, Fujiyama A, Hattori M, Rogers J, Lander ES, Sakaki Y: Human chromosome 11 DNA sequence and analysis including novel gene identification. Nature. 2006 Mar 23;440(7083):497-500. [PubMed Link Image]
  3. Kiefer C, Hessel S, Lampert JM, Vogt K, Lederer MO, Breithaupt DE, von Lintig J: Identification and characterization of a mammalian enzyme catalyzing the asymmetric oxidative cleavage of provitamin A. J Biol Chem. 2001 Apr 27;276(17):14110-6. Epub 2001 Jan 29. [PubMed Link Image]
  4. Lindqvist A, He YG, Andersson S: Cell type-specific expression of beta-carotene 9',10'-monooxygenase in human tissues. J Histochem Cytochem. 2005 Nov;53(11):1403-12. Epub 2005 Jun 27. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available