Hmdb loader
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
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:47 UTC
Update Date2022-03-07 02:52:36 UTC
HMDB IDHMDB0030586
Secondary Accession Numbers
  • HMDB30586
Metabolite Identification
Common Name(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol
Description(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol 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. Based on a literature review a significant number of articles have been published on (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol.
Structure
Data?1563862008
Synonyms
ValueSource
(3S,3'r,4XI)-b,b-carotene-3,3',4-triolGenerator
(3S,3'r,4XI)-β,β-carotene-3,3',4-triolGenerator
3,7-dihydro-1,3-Dimethyl-8-heptyl-1H-purine-2,6-dioneHMDB
Chemical FormulaC40H56O3
Average Molecular Weight584.8708
Monoisotopic Molecular Weight584.422945658
IUPAC Name4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-ene-1,2-diol
Traditional Name4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-ene-1,2-diol
CAS Registry Number97134-07-1
SMILES
C\C(\C=C\C=C(/C)\C=C\C1=C(C)CC(O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(O)C(O)CC1(C)C
InChI Identifier
InChI=1S/C40H56O3/c1-28(17-13-19-30(3)21-23-35-32(5)25-34(41)26-39(35,7)8)15-11-12-16-29(2)18-14-20-31(4)22-24-36-33(6)38(43)37(42)27-40(36,9)10/h11-24,34,37-38,41-43H,25-27H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,28-15+,29-16+,30-19+,31-20+
InChI KeyRNQDFWZVKBSPOZ-ROKXECAJSA-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
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
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
Water Solubility0.00085 g/LALOGPS
logP7.69ALOGPS
logP7.43ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)13.49ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity196.16 m³·mol⁻¹ChemAxon
Polarizability74.3 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+254.61731661259
DarkChem[M-H]-250.29431661259
DeepCCS[M+H]+264.07630932474
DeepCCS[M-H]-262.19530932474
DeepCCS[M-2H]-295.43530932474
DeepCCS[M+Na]+269.81730932474
AllCCS[M+H]+261.832859911
AllCCS[M+H-H2O]+260.132859911
AllCCS[M+NH4]+263.332859911
AllCCS[M+Na]+263.732859911
AllCCS[M-H]-235.832859911
AllCCS[M+Na-2H]-239.932859911
AllCCS[M+HCOO]-244.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triolC\C(\C=C\C=C(/C)\C=C\C1=C(C)CC(O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(O)C(O)CC1(C)C6475.4Standard polar33892256
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triolC\C(\C=C\C=C(/C)\C=C\C1=C(C)CC(O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(O)C(O)CC1(C)C4645.4Standard non polar33892256
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triolC\C(\C=C\C=C(/C)\C=C\C1=C(C)CC(O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(O)C(O)CC1(C)C4514.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol,1TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O)C(O)CC2(C)C)C(C)(C)CC(O[Si](C)(C)C)C14835.6Semi standard non polar33892256
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol,1TMS,isomer #2CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)C(O)CC2(C)C)C(C)(C)CC(O)C14813.9Semi standard non polar33892256
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol,1TMS,isomer #3CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O)C(O[Si](C)(C)C)CC2(C)C)C(C)(C)CC(O)C14811.7Semi standard non polar33892256
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol,2TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)C(O)CC2(C)C)C(C)(C)CC(O[Si](C)(C)C)C14727.1Semi standard non polar33892256
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol,2TMS,isomer #2CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O)C(O[Si](C)(C)C)CC2(C)C)C(C)(C)CC(O[Si](C)(C)C)C14723.5Semi standard non polar33892256
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol,2TMS,isomer #3CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)CC2(C)C)C(C)(C)CC(O)C14769.3Semi standard non polar33892256
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol,3TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)CC2(C)C)C(C)(C)CC(O[Si](C)(C)C)C14693.3Semi standard non polar33892256
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol,1TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O)C(O)CC2(C)C)C(C)(C)CC(O[Si](C)(C)C(C)(C)C)C15059.6Semi standard non polar33892256
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol,1TBDMS,isomer #2CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C(C)(C)C)C(O)CC2(C)C)C(C)(C)CC(O)C15036.7Semi standard non polar33892256
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol,1TBDMS,isomer #3CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O)C(O[Si](C)(C)C(C)(C)C)CC2(C)C)C(C)(C)CC(O)C15039.3Semi standard non polar33892256
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol,2TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C(C)(C)C)C(O)CC2(C)C)C(C)(C)CC(O[Si](C)(C)C(C)(C)C)C15158.2Semi standard non polar33892256
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol,2TBDMS,isomer #2CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O)C(O[Si](C)(C)C(C)(C)C)CC2(C)C)C(C)(C)CC(O[Si](C)(C)C(C)(C)C)C15166.6Semi standard non polar33892256
(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol,2TBDMS,isomer #3CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC2(C)C)C(C)(C)CC(O)C15210.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-0000190000-ea4b887020911d41dbab2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol GC-MS (1 TMS) - 70eV, Positivesplash10-0006-1000019000-072a02383225e9ad89e52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol GC-MS ("(3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol 10V, Positive-QTOFsplash10-014i-0211290000-11f3e5122968b87a0cb12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol 20V, Positive-QTOFsplash10-02ta-0829840000-1351e2fa835745cb48232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol 40V, Positive-QTOFsplash10-000t-2229740000-7a33ac1b33c9905d81a82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol 10V, Negative-QTOFsplash10-001i-0000090000-028e5c7ed39b29c731902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol 20V, Negative-QTOFsplash10-00lr-0000090000-945075278cf07139296c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol 40V, Negative-QTOFsplash10-014i-0221290000-789aac0f74d73dda905a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol 10V, Negative-QTOFsplash10-001i-0101090000-24e77f2806165869ae4b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol 20V, Negative-QTOFsplash10-001i-0115190000-f006cf25f5d4d94ca5ba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol 40V, Negative-QTOFsplash10-0fr5-0329420000-ada50238cfb2a8cfbbbf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol 10V, Positive-QTOFsplash10-000i-0134590000-255980725af8cbe5bd622021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol 20V, Positive-QTOFsplash10-014i-0659880000-d85f07c2910f005030362021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,3'R,4xi)-beta,beta-Carotene-3,3',4-triol 40V, Positive-QTOFsplash10-0159-0139600000-59a26842d67545b9295f2021-09-23Wishart LabView Spectrum
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 IDFDB002479
KNApSAcK IDNot Available
Chemspider ID35013233
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14409074
PDB IDNot Available
ChEBI IDNot Available
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.