Showing metabocard for Astaxanthin (BMDB0002204)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:52:35 UTC
Update Date2020-04-22 15:10:10 UTC
BMDB IDBMDB0002204
Secondary Accession Numbers
  • BMDB02204
Metabolite Identification
Common NameAstaxanthin
DescriptionAstaxanthin, also known as e 161J or ovoester, belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes 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. Xanthophylls arise by oxygenation of the carotene backbone. Thus, astaxanthin is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on Astaxanthin.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3S,3's)-AstaxanthinChEBI
3,3'-Dihydroxy-beta,beta-carotene-4,4'-dioneChEBI
3,3'-Dihydroxy-beta-carotene-4,4'-dioneChEBI
all-trans-(3S,3's)-AstaxanthinChEBI
AstaxanthineChEBI
e 161JChEBI
OvoesterChEBI
(3S,3's)-3,3'-Dihydroxy-beta,beta-carotene-4,4'-dioneKegg
3,3'-Dihydroxy-b,b-carotene-4,4'-dioneGenerator
3,3'-Dihydroxy-β,β-carotene-4,4'-dioneGenerator
3,3'-Dihydroxy-b-carotene-4,4'-dioneGenerator
3,3'-Dihydroxy-β-carotene-4,4'-dioneGenerator
(3S,3's)-3,3'-Dihydroxy-b,b-carotene-4,4'-dioneGenerator
(3S,3's)-3,3'-Dihydroxy-β,β-carotene-4,4'-dioneGenerator
(3S,3's)-all-trans-AstaxanthinHMDB
all-trans-3,3'-Dihydroxy-b-carotene-4,4'-dione (8ci)HMDB
all-trans-3,3'-Dihydroxy-beta-carotene-4,4'-dione (8ci)HMDB
all-trans-AstaxanthinHMDB
AstaREALHMDB
Astaxanthin (6ci)HMDB
BioAstinHMDB
BioAstin oleoresinHMDB
Carophyll pinkHMDB
Lucantin pinkHMDB
NatupinkHMDB
trans-AstaxanthinHMDB
e-AstaxanthinHMDB
(3S,3’S)-3,3’-dihydroxy-β,β-carotene-4,4’-dioneHMDB
(3S,3’S)-astaxanthinHMDB
(3S,3’S)-all-trans-astaxanthinHMDB
(S,S)-AstaxanthinHMDB
all-trans-(3S,3’S)-astaxanthinHMDB
AstaxanthinHMDB
Chemical FormulaC40H52O4
Average Molecular Weight596.852
Monoisotopic Molecular Weight596.386560154
IUPAC Name(6S)-6-hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one
Traditional Nameastaxanthin
CAS Registry Number472-61-7
SMILES
C\C(\C=C\C=C(/C)\C=C\C1=C(C)C(=O)[C@@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(=O)[C@@H](O)CC1(C)C
InChI Identifier
InChI=1S/C40H52O4/c1-27(17-13-19-29(3)21-23-33-31(5)37(43)35(41)25-39(33,7)8)15-11-12-16-28(2)18-14-20-30(4)22-24-34-32(6)38(44)36(42)26-40(34,9)10/h11-24,35-36,41-42H,25-26H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,27-15+,28-16+,29-19+,30-20+/t35-,36-/m0/s1
InChI KeyMQZIGYBFDRPAKN-UWFIBFSHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes 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. Xanthophylls arise by oxygenation of the carotene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentXanthophylls
Alternative Parents
Substituents
  • Xanthophyll
  • Cyclohexenone
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point182.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.4ALOGPS
logP8.05ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)13.07ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity195.98 m³·mol⁻¹ChemAxon
Polarizability73.77 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-001i-2000090000-c6336112eb898c2f0a48View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-3000019000-6b5720849187b199d6bfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Astaxanthin,1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-0961030000-dc7a74c186ee85f204faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-0961030000-368bb77cba4aef27a5cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000090000-ce16b33770cb7a4b2ff7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0232390000-f37e3530214c99f63306View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1296830000-ac8ea41a53a053acb7c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-0185910000-7af6a00762ad7e8ee75dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-248171e80348a7e1d17eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000090000-b9759de23c7494bb7b2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0333390000-074ea5de5d017bafdb5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004m-0142590000-4e72a5bda186fd51912cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-0195650000-3ee8ba797d4a2fb9c80fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01u3-0013900000-71e9a6336700d9e8fca6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0001090000-836dc358b0a566457c26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-0117190000-07d5d205542df36e4f5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-0239230000-7be6270484a4c641a468View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002204
DrugBank IDDB06543
Phenol Explorer Compound IDNot Available
FooDB IDFDB018640
KNApSAcK IDC00000918
Chemspider ID4444636
KEGG Compound IDC08580
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAstaxanthin
METLIN ID3671
PubChem Compound5281224
PDB IDNot Available
ChEBI ID40968
References
Synthesis ReferenceBerg, Michael; Essl, Stefan; Hugentobler, Max. Process for the preparation of astaxanthin. PCT Int. Appl. (2007), 19pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available