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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-12 20:28:08 UTC
Update Date2022-03-07 02:49:18 UTC
HMDB IDHMDB0003415
Secondary Accession Numbers
  • HMDB03415
Metabolite Identification
Common Name(3R,3'S,6'R)-b,e-Carotene-3,3'-diol
Description(3R,3'S,6'R)-Carotene-3,3'-diol is a carotenoid found in human fluids. 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 synthesise 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?1582752275
Synonyms
ValueSource
3'-EpiluteinHMDB
(3R,3's,6'r)-LuteinHMDB
Chemical FormulaC40H56O2
Average Molecular Weight568.886
Monoisotopic Molecular Weight568.428031043
IUPAC Name(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4S)-4-hydroxy-2,6,6-trimethylcyclohex-2-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-en-1-ol
Traditional Name(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4S)-4-hydroxy-2,6,6-trimethylcyclohex-2-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-en-1-ol
CAS Registry Number52842-48-5
SMILES
C\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C
InChI Identifier
InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36-,37+/m1/s1
InChI KeyKBPHJBAIARWVSC-IRHPOQNPSA-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 Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
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 Solubility0.00073 g/LALOGPS
logP8.29ALOGPS
logP8.55ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.22ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity195.06 m³·mol⁻¹ChemAxon
Polarizability73.36 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
DeepCCS[M+H]+259.70530932474
DeepCCS[M-H]-257.81230932474
DeepCCS[M-2H]-291.84630932474
DeepCCS[M+Na]+265.82430932474
AllCCS[M+H]+259.332859911
AllCCS[M+H-H2O]+257.632859911
AllCCS[M+NH4]+260.932859911
AllCCS[M+Na]+261.332859911
AllCCS[M-H]-231.032859911
AllCCS[M+Na-2H]-234.632859911
AllCCS[M+HCOO]-238.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(3R,3'S,6'R)-b,e-Carotene-3,3'-diolC\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C6137.6Standard polar33892256
(3R,3'S,6'R)-b,e-Carotene-3,3'-diolC\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C4714.4Standard non polar33892256
(3R,3'S,6'R)-b,e-Carotene-3,3'-diolC\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C4370.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(3R,3'S,6'R)-b,e-Carotene-3,3'-diol,1TMS,isomer #1CC1=C[C@@H](O[Si](C)(C)C)CC(C)(C)[C@H]1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C4765.9Semi standard non polar33892256
(3R,3'S,6'R)-b,e-Carotene-3,3'-diol,1TMS,isomer #2CC1=C[C@@H](O)CC(C)(C)[C@H]1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C)CC1(C)C4758.6Semi standard non polar33892256
(3R,3'S,6'R)-b,e-Carotene-3,3'-diol,2TMS,isomer #1CC1=C[C@@H](O[Si](C)(C)C)CC(C)(C)[C@H]1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C)CC1(C)C4721.6Semi standard non polar33892256
(3R,3'S,6'R)-b,e-Carotene-3,3'-diol,1TBDMS,isomer #1CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)[C@H]1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C4963.0Semi standard non polar33892256
(3R,3'S,6'R)-b,e-Carotene-3,3'-diol,1TBDMS,isomer #2CC1=C[C@@H](O)CC(C)(C)[C@H]1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C4955.0Semi standard non polar33892256
(3R,3'S,6'R)-b,e-Carotene-3,3'-diol,2TBDMS,isomer #1CC1=C[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)[C@H]1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C5160.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uk9-1000190000-79574985e26da720cbd62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol GC-MS (1 TMS) - 70eV, Positivesplash10-004i-3100039000-baee6b30a2822c0614772017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol GC-MS ("(3R,3'S,6'R)-b,e-Carotene-3,3'-diol,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol 10V, Negative-QTOFsplash10-014i-0000090000-cbb0d37d0ab268305e5e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol 20V, Negative-QTOFsplash10-014i-0000090000-d81cdc000e19ba6b5a352017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol 40V, Negative-QTOFsplash10-0uxr-0343390000-ff8fd45055c84409ffdb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol 10V, Negative-QTOFsplash10-014i-0202090000-e7ff503087b0472872342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol 20V, Negative-QTOFsplash10-014i-0405490000-4908259aa27c690d5b582021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol 40V, Negative-QTOFsplash10-0201-0519300000-3ec7b022b5aedb2ab3d02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol 10V, Positive-QTOFsplash10-0gb9-0201190000-12a2e7baec2965c164cf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol 20V, Positive-QTOFsplash10-0002-0829330000-021e7fc06b639da39e2c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol 40V, Positive-QTOFsplash10-000b-3339330000-4e6e49a5efd708c6c9712017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol 10V, Positive-QTOFsplash10-014r-0121930000-b93c4284d63c87f0039c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol 20V, Positive-QTOFsplash10-0uel-0113920000-f619218ed5b32e075e702021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3R,3'S,6'R)-b,e-Carotene-3,3'-diol 40V, Positive-QTOFsplash10-0wmi-0059500000-ba48ee62bc6ea7e22dbf2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB112373
KNApSAcK IDC00022872
Chemspider ID8385504
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10210008
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. 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 ]