You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 08:42:22 UTC
Update Date2017-12-07 01:53:08 UTC
HMDB IDHMDB0003993
Secondary Accession Numbers
  • HMDB03993
Metabolite Identification
Common NameAlpha-Carotene
DescriptionApha-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 ).
Structure
Thumb
Synonyms
ValueSource
all-trans-alpha-CaroteneChEBI
all-trans-a-CaroteneGenerator
all-trans-α-caroteneGenerator
a-CaroteneGenerator
α-caroteneGenerator
(+)-alpha-CaroteneHMDB
(6'r)-beta,epsilon-CaroteneHMDB
BCRHMDB
beta,epsilon-CaroteneHMDB
Hi-alphaHMDB
alpha-Carotene, (6'r)-isomerMeSH
Chemical FormulaC40H56
Average Molecular Weight536.888
Monoisotopic Molecular Weight536.438201803
IUPAC Name1,5,5-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 Nameα-carotene
CAS Registry Number7488-99-5
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 KeyANVAOWXLWRTKGA-JLTXGRSLSA-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
  • Cycloalkene
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Organ and components:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point187.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00031 g/LALOGPS
logP9.79ALOGPS
logP11.17ChemAxon
logS-6.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity191.88 m³·mol⁻¹ChemAxon
Polarizability71.27 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-7511590000-5ff377447b1a3120b90bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0434290000-6f904a3c295bc1e6ac54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001s-0957200000-351f26ece1b0df197b1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004s-1868900000-f5489f2f18f85eed5cb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000090000-e93c3c9ed8db3b98e043View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000090000-60cec21bb7939f633e51View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0947570000-8f7580b6f95f904737f6View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Breast Milk
Tissue Location
  • Adipose Tissue
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.05 +/- 0.04 uMAdolescent (13-18 years old)Female
Normal
details
BloodDetected and Quantified0.04 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.06 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.031 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.208 +/- 0.00600 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0500 +/- 0.0500 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0500 +/- 0.0500 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0900 +/- 0.0400 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0900 +/- 0.0600 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0700 +/- 0.0500 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0700 +/- 0.0500 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0960 +/- 0.140 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.117 +/- 0.0870 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0610 +/- 0.0700 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.0700 +/- 0.0500 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.0700 +/- 0.0600 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.0820 +/- 0.0530 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.140 +/- 0.230 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.150 +/- 0.130 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.110 +/- 0.120 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.0987 +/- 0.0801 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.180 +/- 0.200 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.190 +/- 0.190 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.1 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified3.25 (0.90-5.60) uMAdult (>18 years old)Not SpecifiedNormal
    • The Merck Manual,...
details
BloodDetected and Quantified0.07 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified110 +/- 80 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0913 +/- 0.0708 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0900 +/- 0.0500 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0800 +/- 0.0500 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.0555 +/- 0.0669 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.07 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.08 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.051 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.146 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.514 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.601 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.12 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.238 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.282 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.098 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0986 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.112 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0400 +/- 0.0200 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0500 +/- 0.0300 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0764 +/- 0.121 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0969 +/- 0.0782 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.104 +/- 0.0801 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.110 +/- 0.0800 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.120 +/- 0.110 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.07 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.108 uMChildren (1-13 years old)FemaleNormal details
BloodDetected and Quantified0.11 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.11 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.13 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.2 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0736 +/- 0.0514 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0820 +/- 0.0894 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.104 +/- 0.0857 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.117 +/- 0.0913 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.120 +/- 0.0900 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.120 +/- 0.100 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.140 +/- 0.0700 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.180 +/- 0.151 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified124.980 +/- 97.599 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified186.259 +/- 93.129 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.07 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.08 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.093 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.117 uMChildren (1-13 years old)MaleNormal details
BloodDetected and Quantified0.12 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0503 +/- 0.0373 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0503 +/- 0.0484 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0689 +/- 0.0428 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0689 +/- 0.0894 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0810 +/- 0.0600 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0880 +/- 0.0730 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0911 +/- 0.0577 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.110 +/- 0.100 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.120 +/- 0.0600 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.135 +/- 0.0920 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified113.990 +/- 103.187 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified70 +/- 60 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified90 +/- 70 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified130.381 +/- 74.503 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.120 +/- 0.0900 uMChildren (1 - 13 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.11 +/- 0.09 uMAdult (>18 years old)BothNormal details
Breast MilkDetected but not Quantified Adult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0590 +/- 0.0500 uMAdult (>18 years old)Not Specified
Obese
details
BloodDetected and Quantified0.0770 +/- 0.0800 uMAdult (>18 years old)Not Specified
Overweight
details
BloodDetected and Quantified71000 uMAdult (>18 years old)Both
Colorectal, breast, or neuroendocrine cancer
details
BloodDetected and Quantified0.0800 +/- 0.0700 uMAdult (>18 years old)BothType I diabetes details
BloodDetected and Quantified0.0500 +/- 0.0400 uMChildren (1 - 13 years old)Not SpecifiedObese details
BloodDetected and Quantified0.0800 +/- 0.0600 uMChildren (1 - 13 years old)Not SpecifiedOverweight details
BloodDetected and Quantified0.12 +/- 0.11 uMAdult (>18 years old)BothAfter tomato drink intake details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB013716
KNApSAcK IDC00003765
Chemspider ID3571861
KEGG Compound IDC05433
BioCyc IDCPD1F-118
BiGG IDNot Available
Wikipedia LinkBCR
METLIN ID6998
PubChem Compound4369188
PDB IDNot Available
ChEBI ID28425
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  14. Yu MW, Chiang YC, Lien JP, Chen CJ: Plasma antioxidant vitamins, chronic hepatitis B virus infection and urinary aflatoxin B1-DNA adducts in healthy males. Carcinogenesis. 1997 Jun;18(6):1189-94. [PubMed:9214602 ]