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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:16:42 UTC
Update Date2022-03-07 02:54:27 UTC
HMDB IDHMDB0035317
Secondary Accession Numbers
  • HMDB35317
Metabolite Identification
Common Namealpha-Bixin
Descriptionalpha-Bixin, also known as a-bixin, belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Based on a literature review a significant number of articles have been published on alpha-Bixin.
Structure
Data?1563862699
Synonyms
ValueSource
6'-Methyl hydrogen 9'-cis-6,6'-diapocarotene-6,6'-dioateChEBI
6'-Methyl hydrogen 9'-Z-6,6'-diapocarotene-6,6'-dioateChEBI
Methyl (9-cis)-hydrogen-6,6'-diapo-psi,psi-carotenedioateChEBI
6'-Methyl hydrogen 9'-cis-6,6'-diapocarotene-6,6'-dioic acidGenerator
6'-Methyl hydrogen 9'-Z-6,6'-diapocarotene-6,6'-dioic acidGenerator
Methyl (9-cis)-hydrogen-6,6'-diapo-psi,psi-carotenedioic acidGenerator
a-BixinGenerator
Α-bixinGenerator
IsobixinHMDB
Stable bixinHMDB
Chemical FormulaC25H30O4
Average Molecular Weight394.5033
Monoisotopic Molecular Weight394.214409448
IUPAC Name(2E,4E,6E,8E,10E,12E,14E,16Z,18E)-20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid
Traditional Namebixin
CAS Registry Number6983-79-5
SMILES
COC(=O)\C=C\C(\C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C(O)=O
InChI Identifier
InChI=1S/C25H30O4/c1-20(12-8-14-22(3)16-18-24(26)27)10-6-7-11-21(2)13-9-15-23(4)17-19-25(28)29-5/h6-19H,1-5H3,(H,26,27)/b7-6+,12-8+,13-9+,18-16+,19-17+,20-10+,21-11+,22-14+,23-15-
InChI KeyRAFGELQLHMBRHD-SLEZCNMESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentAcyclic diterpenoids
Alternative Parents
Substituents
  • Acyclic diterpenoid
  • Long-chain fatty acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Unsaturated fatty acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point189.5 - 190.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0014 g/LALOGPS
logP6ALOGPS
logP5.53ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)5.01ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity129.05 m³·mol⁻¹ChemAxon
Polarizability47.1 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+209.48331661259
DarkChem[M-H]-212.05931661259
DeepCCS[M+H]+215.45130932474
DeepCCS[M-H]-213.09330932474
DeepCCS[M-2H]-245.99730932474
DeepCCS[M+Na]+221.54430932474
AllCCS[M+H]+206.532859911
AllCCS[M+H-H2O]+203.832859911
AllCCS[M+NH4]+209.032859911
AllCCS[M+Na]+209.732859911
AllCCS[M-H]-190.632859911
AllCCS[M+Na-2H]-192.032859911
AllCCS[M+HCOO]-193.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-BixinCOC(=O)\C=C\C(\C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C(O)=O5707.9Standard polar33892256
alpha-BixinCOC(=O)\C=C\C(\C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C(O)=O3316.8Standard non polar33892256
alpha-BixinCOC(=O)\C=C\C(\C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C(O)=O3578.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Bixin,1TMS,isomer #1COC(=O)/C=C/C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(C)\C=C\C(=O)O[Si](C)(C)C3502.0Semi standard non polar33892256
alpha-Bixin,1TBDMS,isomer #1COC(=O)/C=C/C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(C)\C=C\C(=O)O[Si](C)(C)C(C)(C)C3704.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Bixin GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0329000000-4df19b811a15fe42f2482017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Bixin GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-4114900000-ee8fbc6ef75ce2439c912017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Bixin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Bixin 10V, Positive-QTOFsplash10-0002-0109000000-5c422928e89256a05ae42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Bixin 20V, Positive-QTOFsplash10-014s-0669000000-5e07666a82b6b7454eed2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Bixin 40V, Positive-QTOFsplash10-0r01-5951000000-6325f3b9011cd6981db42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Bixin 10V, Negative-QTOFsplash10-0006-0009000000-c4ce0b9da065aa5ffc362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Bixin 20V, Negative-QTOFsplash10-01ox-1009000000-52d5a9deb379ba21cb8c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Bixin 40V, Negative-QTOFsplash10-0a4l-9018000000-74943b731b94855147812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Bixin 10V, Positive-QTOFsplash10-02i2-0069000000-0e02593a769ab2fae3a92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Bixin 20V, Positive-QTOFsplash10-08gr-2096000000-2feaaace65be9aa5c43b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Bixin 40V, Positive-QTOFsplash10-0pc0-3691000000-98c1007a360d276c80e22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Bixin 10V, Negative-QTOFsplash10-00ke-0029000000-9d444e971722024126502021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Bixin 20V, Negative-QTOFsplash10-0ab9-6059000000-c32a898c36431399c8672021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Bixin 40V, Negative-QTOFsplash10-0296-2095000000-e2e7d0c73c13e98a85c62021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB013987
KNApSAcK IDC00003762
Chemspider ID4444638
KEGG Compound IDC08582
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBixin
METLIN IDNot Available
PubChem Compound5281226
PDB IDNot Available
ChEBI ID3136
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.