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Human Metabolome Database Version 3.5

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Showing metabocard for Alpha-Carotene (HMDB03993)

Record Information
Version 3.5
Creation Date 2006-08-13 02:42:22 -0600
Update Date 2013-05-13 17:08:43 -0600
HMDB ID HMDB03993
Secondary Accession Numbers None
Metabolite Identification
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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (+)-alpha-Carotene
  2. (6'R)-beta,epsilon-Carotene
  3. All-trans-alpha-Carotene
  4. alpha-Carotene
  5. BCR
  6. beta,epsilon-Carotene
  7. Hi-alpha
Chemical Formula C40H56
Average Molecular Weight 536.8726
Monoisotopic Molecular Weight 536.438201792
IUPAC Name 1,5,5-trimethyl-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene
Traditional IUPAC Name α-carotene
CAS Registry Number 7488-99-5
SMILES C\C(\C=C\C=C(/C)\C=C\C1C(C)=CCCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C
InChI Identifier InChI=1S/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+
InChI Key ANVAOWXLWRTKGA-JLTXGRSLSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Tetraterpenes
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • C40 isoprenoids (tetraterpenes)(Lipidmaps)
  • Carotenes
  • alpha-carotene(ChEBI)
Substituents
  • Cyclohexene
  • Isoprene
Direct Parent Carotenoids
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 187.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 9.79 ALOGPS
LogP 11.17 ChemAxon
LogS -6.24 ALOGPS
Hydrogen Acceptor Count 0 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 0 A2 ChemAxon
Rotatable Bond Count 10 ChemAxon
Refractivity 191.88 ChemAxon
Polarizability 71.26 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Liver
  • Adipose Tissue
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.05 +/- 0.04 uM Adolescent (13-18 years old) Female Normal Lactating mothers
Blood Detected and Quantified
Article_icon
3.25 (0.90-5.60) uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and Quantified
Article_icon
0.11 +/- 0.09 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.12 +/- 0.11 uM Adult (>18 years old) Both After tomato drink intake Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB013716
KNApSAcK ID C00003765 Link_out
Chemspider ID 3571861 Link_out
KEGG Compound ID C05433 Link_out
BioCyc ID CPD1F-118 Link_out
BiGG ID Not Available
Wikipedia Link BCR Link_out
NuGOwiki Link HMDB03993 Link_out
Metagene Link HMDB03993 Link_out
METLIN ID 6998 Link_out
PubChem Compound 4369188 Link_out
PDB ID Not Available
ChEBI ID 28425 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
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: 15045249 Link_out
  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: 8583143 Link_out
  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: 1423303 Link_out
  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: 10653337 Link_out
  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: 12385452 Link_out
  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: 12811470 Link_out
  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: 10381285 Link_out
  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: 12081831 Link_out
  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: 8916508 Link_out
  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: 1765826 Link_out
  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: 8839500 Link_out
  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: 10856518 Link_out
  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: 8487096 Link_out