Hmdb loader
Survey
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
Version5.0
StatusDetected but not Quantified
Creation Date2017-09-08 16:53:52 UTC
Update Date2020-03-12 17:29:07 UTC
HMDB IDHMDB0112264
Secondary Accession Numbers
  • HMDB0002935
  • HMDB02935
Metabolite Identification
Common Name9-cis-beta-Carotene
Description9-cis-beta-Carotene is a cyclic carotene having the structure of beta-carotene but with a cis double bond at the 9,10-position. It is found in human serum and breast milk (PMID: 9164160 ). Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds, and crustacea. Animals are unable to synthesize carotenoids de novo and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer-preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important (PMID: 1416048 , 15003396 ).
Structure
Data?1584034147
Synonyms
ValueSource
9-cis-β-CaroteneHMDB, Generator
9-cis-b-CaroteneGenerator
(9Z)-beta,beta-CaroteneHMDB
(9Z)-beta-CaroteneHMDB
(9Z)-β,β-CaroteneHMDB
(9Z)-β-CaroteneHMDB
9-cis-beta,beta-CaroteneHMDB
9-cis-beta-CaroteneHMDB
9-cis-β,β-CaroteneHMDB
Chemical FormulaC40H56
Average Molecular Weight536.888
Monoisotopic Molecular Weight536.438201803
IUPAC Name1,3,3-trimethyl-2-[(1E,3Z,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 Name1,3,3-trimethyl-2-[(1E,3Z,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
CAS Registry Number13312-52-2
SMILES
C/C(/C=C/C=C(/C)\C=C\C1=C(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/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21-,34-22+
InChI KeyOENHQHLEOONYIE-BVZAMQQESA-N
Chemical Taxonomy
Description 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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP9.72ALOGPS
logP11.12ChemAxon
logS-6.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity191.61 m³·mol⁻¹ChemAxon
Polarizability70.68 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+241.85631661259
DarkChem[M-H]-241.90131661259
DeepCCS[M+H]+251.46430932474
DeepCCS[M-H]-249.54530932474
DeepCCS[M-2H]-282.78630932474
DeepCCS[M+Na]+257.32730932474
AllCCS[M+H]+251.732859911
AllCCS[M+H-H2O]+249.932859911
AllCCS[M+NH4]+253.332859911
AllCCS[M+Na]+253.832859911
AllCCS[M-H]-225.032859911
AllCCS[M+Na-2H]-228.132859911
AllCCS[M+HCOO]-231.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
9-cis-beta-CaroteneC/C(/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C4726.2Standard polar33892256
9-cis-beta-CaroteneC/C(/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C4495.9Standard non polar33892256
9-cis-beta-CaroteneC/C(/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C4194.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 9-cis-beta-Carotene GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-3211290000-f968c686d39ae0f0fc502017-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-cis-beta-Carotene QIT 20V, positive-QTOFsplash10-0006-0000900000-e2b4bab05a7025f386112020-07-21HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-cis-beta-Carotene 10V, Positive-QTOFsplash10-000i-0434190000-0f2f0f2c4af76e6c33222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-cis-beta-Carotene 20V, Positive-QTOFsplash10-000b-0679100000-6f4450c8ade1963f92012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-cis-beta-Carotene 40V, Positive-QTOFsplash10-000j-1789100000-6f2a7024e42303e7737a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-cis-beta-Carotene 10V, Negative-QTOFsplash10-000i-0000090000-cdea7c2d939f0c68b9052016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-cis-beta-Carotene 20V, Negative-QTOFsplash10-000i-0000090000-530c81799c9daabdc9bf2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-cis-beta-Carotene 40V, Negative-QTOFsplash10-014i-0968170000-ec71ee19e546088e3b052016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-cis-beta-Carotene 10V, Positive-QTOFsplash10-000j-0277960000-5b1eef16ffbc2ccd4b1e2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-cis-beta-Carotene 20V, Positive-QTOFsplash10-0081-0449400000-e362d306c4b151321fb62021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-cis-beta-Carotene 40V, Positive-QTOFsplash10-0iki-0149200000-5b858e5700ff1d750a4e2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-cis-beta-Carotene 10V, Negative-QTOFsplash10-000i-0001090000-b0a4df7c3417e82842d72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-cis-beta-Carotene 20V, Negative-QTOFsplash10-000j-0135090000-fb91b96b3605a056f12f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-cis-beta-Carotene 40V, Negative-QTOFsplash10-0apj-0229000000-23e454829ef21fbedf662021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Breast Milk
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
Breast MilkDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023083
KNApSAcK IDNot Available
Chemspider ID8004366
KEGG Compound IDC20484
BioCyc IDCPD-14646
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9828626
PDB IDNot Available
ChEBI ID67188
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. Khachik F, Beecher GR, Goli MB, Lusby WR, Smith JC Jr: Separation and identification of carotenoids and their oxidation products in the extracts of human plasma. Anal Chem. 1992 Sep 15;64(18):2111-22. [PubMed:1416048 ]
  2. Fraser PD, Bramley PM: The biosynthesis and nutritional uses of carotenoids. Prog Lipid Res. 2004 May;43(3):228-65. [PubMed:15003396 ]
  3. Khachik F, Spangler CJ, Smith JC Jr, Canfield LM, Steck A, Pfander H: Identification, quantification, and relative concentrations of carotenoids and their metabolites in human milk and serum. Anal Chem. 1997 May 15;69(10):1873-81. [PubMed:9164160 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.