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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:44:54 UTC
Update Date2019-01-11 19:52:03 UTC
HMDB IDHMDB0036590
Secondary Accession Numbers
  • HMDB36590
Metabolite Identification
Common NameCapsanthin
DescriptionCapsanthin is found in green vegetables. Capsanthin is a constituent of paprika (Capsicum annuum) and asparagus (Asparagus officinalis). Potential nutriceutical.Paprika oleoresin (also known as paprika extract) is an oil soluble extract from the fruits of Capsicum Annum Linn or Capsicum Frutescens(Indian red chillies), and is primarily used as a colouring and/or flavouring in food products. It is composed of capsaicin, the main flavouring compound giving pungency in higher concentrations, and capsanthin and capsorubin, the main colouring compounds (among other carotenoids)
Structure
Data?1547236323
Synonyms
ValueSource
(3R,3's,5'r)-3,3'-Dihydroxy-beta,kappa-caroten-6'-oneHMDB
3,3'-Dihydroxy-b,K-caroten-6'-oneHMDB
3,3'-Dihydroxy-beta,kappa-caroten-6'oneHMDB
3,3'Dihydroxy-beta,kappa-caroten-6'oneHMDB
Capsanthin/capsorubinHMDB
Paprika extractHMDB
Chemical FormulaC40H56O3
Average Molecular Weight584.8708
Monoisotopic Molecular Weight584.422945658
IUPAC Name(2E,4Z,6E,8E,10E,12E,14E,16Z,18E)-1-(4-hydroxy-1,2,2-trimethylcyclopentyl)-19-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
Traditional Name(2E,4Z,6E,8E,10E,12E,14E,16Z,18E)-1-(4-hydroxy-1,2,2-trimethylcyclopentyl)-19-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
CAS Registry Number465-42-9
SMILES
C/C(/C=C/C=C(/C)\C=C\C(=O)C1(C)CC(O)CC1(C)C)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CC(O)CC1(C)C
InChI Identifier
InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-23-36-33(5)25-34(41)26-38(36,6)7)15-11-12-16-30(2)18-14-20-32(4)22-24-37(43)40(10)28-35(42)27-39(40,8)9/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19-,32-20-
InChI KeyVYIRVAXUEZSDNC-QGLVDCRNSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Cyclopentanol
  • Alpha,beta-unsaturated ketone
  • Enone
  • Cyclic alcohol
  • Acryloyl-group
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point175 - 176 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00068 g/LALOGPS
logP8.2ALOGPS
logP8.51ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)15.21ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity194.96 m³·mol⁻¹ChemAxon
Polarizability73.9 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-1000390000-9168df6e83b6f3559682JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-2100219000-d6685bf191ff1d9cf61dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0110290000-8efbbb300dc99ca54e94JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-0635960000-c46df5f79c0b8400f6ffJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07dk-0946620000-b7f05289e89d51313099JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0100090000-cccefbb02a471fcf8ba5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-0200390000-14a64216d2c88e3204abJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uy0-0600590000-34c915ac447d608bc04aJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015502
KNApSAcK IDC00003763
Chemspider ID8048820
KEGG Compound IDC08584
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPaprika oleoresin
METLIN IDNot Available
PubChem Compound9873131
PDB IDNot Available
ChEBI ID3375
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhang X, Zhao WE, Hu L, Zhao L, Huang J: Carotenoids inhibit proliferation and regulate expression of peroxisome proliferators-activated receptor gamma (PPARgamma) in K562 cancer cells. Arch Biochem Biophys. 2011 Aug 1;512(1):96-106. doi: 10.1016/j.abb.2011.05.004. Epub 2011 May 18. [PubMed:21620794 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.