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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:06:40 UTC
Update Date2019-07-23 06:22:30 UTC
HMDB IDHMDB0036924
Secondary Accession Numbers
  • HMDB36924
Metabolite Identification
Common NameCapsorubin
DescriptionCapsorubin, also known as E160 (capsorubin), belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, capsorubin is considered to be an isoprenoid lipid molecule. Capsorubin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563862950
Synonyms
ValueSource
(3S,5R,3's,5'r)-3,3'-Dihydroxy-kappa,kappa-carotene-6,6'-dioneChEBI
all-trans-CapsorubinChEBI
3,3'-Dihydroxy-K,K-carotene-6,6'-dioneHMDB
e160 (Capsorubin)HMDB
3,3'-Dihyroxy-kappa,kappa-carotene-6,6'-dioneMeSH
Chemical FormulaC40H56O4
Average Molecular Weight600.884
Monoisotopic Molecular Weight600.417860283
IUPAC Name(2E,4E,6E,8E,10E,12E,14E,16E,18E)-1,20-bis[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaene-1,20-dione
Traditional Namecapsorubin
CAS Registry Number470-38-2
SMILES
C\C(\C=C\C=C(/C)\C=C\C(=O)[C@]1(C)C[C@@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C(=O)[C@]1(C)C[C@@H](O)CC1(C)C
InChI Identifier
InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-35(43)39(9)27-33(41)25-37(39,5)6)15-11-12-16-30(2)18-14-20-32(4)22-24-36(44)40(10)28-34(42)26-38(40,7)8/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,39-,40-/m0/s1
InChI KeyGVOIABOMXKDDGU-YUURSNASSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • 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 Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point201 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00073 g/LALOGPS
logP7.43ALOGPS
logP8.66ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)14.91ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity194.98 m³·mol⁻¹ChemAxon
Polarizability74.42 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05g0-5100590000-fad54212543d1f512984Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0aba-5200339000-ff900d90febfca9895c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0212395000-f19755cd410fc84063a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02aj-0546961000-158fc904cfdc70c93f7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-0734910000-c2dc526d491dfb9ce812Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0100090000-d7846c55efda3484365bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0300390000-5b288631aba89082ff43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zir-1700490000-523df8c61745082684d9Spectrum
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
FooDB IDFDB015893
KNApSAcK IDC00003764
Chemspider ID4444641
KEGG Compound IDC08585
BioCyc IDCAPSORUBIN
BiGG IDNot Available
Wikipedia LinkPaprika oleoresin
METLIN IDNot Available
PubChem Compound5281229
PDB IDNot Available
ChEBI ID3378
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.