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Human Metabolome Database Version 2.5

 

Showing metabocard for Alpha-Carotene (HMDB03993)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-08-13 09:42:22
Update Date 2009-08-04 12:08:06
Accession Number HMDB03993
Secondary Accession Numbers Not Available
Common Name Alpha-Carotene
Description Apha-carotene is one of the primary isomer of carotene. plasma levels of alpha-carotene is positively associated with the detection rate of (theaflatoxin B1)AFB1-DNA adducts in a dose-dependent manner, whereas plasma lycopene level was inversely related to the presence of the adducts in urine.(PMID: 9214602)
Synonyms
  1. (+)-alpha-Carotene
  2. (6'R)-beta,epsilon-Carotene
  3. BCR
  4. Hi-Alpha
  5. all-trans-alpha-Carotene
  6. alpha-Carotene
  7. beta,epsilon-Carotene
Chemical IUPAC Name (1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-1-(2,6,6-trimethyl-1-cyclohexenyl)-18-(2,6,6-trimethyl-1-cyclohex-2-enyl)octadeca-1,3,5,7,9,11,13,15,17-nonaene
Chemical Formula C40H56
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Miscellanous
Class
  • Alkanes and Alkenes
Sub Class
  • Carotenes
Family
  • Mammalian Metabolite
Species
  • alkene
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 536.873
Monoisotopic Molecular Weight 536.438232
Isomeric SMILES CC(C=CC=C(C)C=CC1C(C)=CCCC1(C)C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C
Canonical SMILES CC(C=CC=C(C)C=CC1C(C)=CCCC1(C)C)=CC=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C
KEGG Compound ID C05433 Link Image
BioCyc ID CPD1F-118 Link Image
BiGG ID Not Available
Wikipedia Link BCR Link Image
NuGOwiki Link HMDB03993 Link Image
Metagene Link HMDB03993 Link Image
METLIN ID 6998 Link Image
PubChem Compound 4369188 Link Image
PubChem Substance 823343 Link Image
ChEBI ID 35147 Link Image
CAS Registry Number 7488-99-5
InChI Identifier InChI=1/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-23,25-28,37H,15-16,24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+
Synthesis Reference Not Available
Melting Point (Experimental) 187.5 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1.02e-17 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]; 3.07e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 9.79 [Predicted by ALOGPS]; 10.782 [Predicted by PubChem via XLOGP]; 17.49 [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 —
Liver —
Concentrations (Normal)
Biofluid Blood
Value 3.25 (0.90-5.60) uM
Age Adult:>18 yrs old
Sex N/A
Patient information Normal
Comments Not Available
References
  • The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.
Biofluid Blood
Value 0.05 +/- 0.04 uM
Age Adolescent:13-18 yrs old
Sex Female
Patient information Lactating mothers
Comments blood plasma
References
  • de Azeredo VB, Trugo NM: Retinol, carotenoids, and tocopherols in the milk of lactating adolescents and relationships with plasma concentrations. Nutrition. 2008 Feb;24(2):133-9. Epub 2007 Dec 3. [PubMed Link Image]
Biofluid Blood
Value 0.11 +/- 0.09 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 0.12 +/- 0.11 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 Not Available
OMIM ID Not Available
Pathways Not Available
General References
  1. Thomas JB, Kline MC, Schiller SB, Ellerbe PM, Sniegoski LT, Duewer DL, Sharpless KE: Certification of fat-soluble vitamins, carotenoids, and cholesterol in human serum: Standard Reference Material 968b. Anal Bioanal Chem. 1996 Aug;356(1):1-9. [PubMed Link Image]
  2. Leo MA, Ahmed S, Aleynik SI, Siegel JH, Kasmin F, Lieber CS: Carotenoids and tocopherols in various hepatobiliary conditions. J Hepatol. 1995 Nov;23(5):550-6. [PubMed Link Image]
  3. Murakoshi M, Nishino H, Satomi Y, Takayasu J, Hasegawa T, Tokuda H, Iwashima A, Okuzumi J, Okabe H, Kitano H, et al.: Potent preventive action of alpha-carotene against carcinogenesis: spontaneous liver carcinogenesis and promoting stage of lung and skin carcinogenesis in mice are suppressed more effectively by alpha-carotene than by beta-carotene. Cancer Res. 1992 Dec 1;52(23):6583-7. [PubMed Link Image]
  4. Sommerburg O, Meissner K, Nelle M, Lenhartz H, Leichsenring M: Carotenoid supply in breast-fed and formula-fed neonates. Eur J Pediatr. 2000 Jan-Feb;159(1-2):86-90. [PubMed Link Image]
  5. Yadav D, Hertan HI, Schweitzer P, Norkus EP, Pitchumoni CS: Serum and liver micronutrient antioxidants and serum oxidative stress in patients with chronic hepatitis C. Am J Gastroenterol. 2002 Oct;97(10):2634-9. [PubMed Link Image]
  6. Canfield LM, Clandinin MT, Davies DP, Fernandez MC, Jackson J, Hawkes J, Goldman WJ, Pramuk K, Reyes H, Sablan B, Sonobe T, Bo X: Multinational study of major breast milk carotenoids of healthy mothers. Eur J Nutr. 2003 Jun;42(3):133-41. [PubMed Link Image]
  7. Kontush A, Spranger T, Reich A, Baum K, Beisiegel U: Lipophilic antioxidants in blood plasma as markers of atherosclerosis: the role of alpha-carotene and gamma-tocopherol. Atherosclerosis. 1999 May;144(1):117-22. [PubMed Link Image]
  8. El-Sohemy A, Baylin A, Kabagambe E, Ascherio A, Spiegelman D, Campos H: Individual carotenoid concentrations in adipose tissue and plasma as biomarkers of dietary intake. Am J Clin Nutr. 2002 Jul;76(1):172-9. [PubMed Link Image]
  9. Virtanen SM, van't Veer P, Kok F, Kardinaal AF, Aro A: Predictors of adipose tissue carotenoid and retinol levels in nine countries. The EURAMIC Study. Am J Epidemiol. 1996 Nov 15;144(10):968-79. [PubMed Link Image]
  10. Schmitz HH, Poor CL, Wellman RB, Erdman JW Jr: Concentrations of selected carotenoids and vitamin A in human liver, kidney and lung tissue. J Nutr. 1991 Oct;121(10):1613-21. [PubMed Link Image]
  11. Forman MR, Beecher GR, Muesing R, Lanza E, Olson B, Campbell WS, McAdam P, Raymond E, Schulman JD, Graubard BI: The fluctuation of plasma carotenoid concentrations by phase of the menstrual cycle: a controlled diet study. Am J Clin Nutr. 1996 Oct;64(4):559-65. [PubMed Link Image]
  12. Martin KR, Wu D, Meydani M: The effect of carotenoids on the expression of cell surface adhesion molecules and binding of monocytes to human aortic endothelial cells. Atherosclerosis. 2000 Jun;150(2):265-74. [PubMed Link Image]
  13. Stahl W, Schwarz W, Sies H: Human serum concentrations of all-trans beta- and alpha-carotene but not 9-cis beta-carotene increase upon ingestion of a natural isomer mixture obtained from Dunaliella salina (Betatene). J Nutr. 1993 May;123(5):847-51. [PubMed Link Image]
  14. Wikipedia Link Image