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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2017-09-08 16:51:47 UTC
Update Date2021-09-14 14:57:36 UTC
HMDB IDHMDB0112256
Secondary Accession NumbersNone
Metabolite Identification
Common NameLactucaxanthin
DescriptionLactucaxanthin is a tunaxanthin that consists of ε,ε-carotene bearing hydroxy substituents at positions 3 and 3' (the 3S,3'S,6S,6'S-diastereomer) (ChEBI: 6357). It is a carotenoid 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 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?1563873235
Synonyms
ValueSource
(3S,3's,6S,6's)-Ε,ε-carotene-3,3'-diolHMDB
(3S,3's,6S,6's)-epsilon,epsilon-Carotene-3,3'-diolHMDB
Tunaxanthin FHMDB
LactucaxanthinSMPDB
Chemical FormulaC40H56O2
Average Molecular Weight568.886
Monoisotopic Molecular Weight568.428031043
IUPAC Name(1R,4R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-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-2-en-1-ol
Traditional Namelactucaxanthin
CAS Registry Number78306-12-4
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/[C@H]1C(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/h11-26,35-38,41-42H,27-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36-,37-,38-/m0/s1
InChI KeyBIPAHAFBQLWRMC-SUOWZELTSA-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
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
logP8.31ALOGPS
logP8.75ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)18.22ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity195.18 m³·mol⁻¹ChemAxon
Polarizability74.13 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]+256.04630932474
DeepCCS[M-H]-254.26230932474
DeepCCS[M-2H]-288.29430932474
DeepCCS[M+Na]+262.25730932474
AllCCS[M+H]+259.232859911
AllCCS[M+H-H2O]+257.532859911
AllCCS[M+NH4]+260.832859911
AllCCS[M+Na]+261.232859911
AllCCS[M-H]-230.832859911
AllCCS[M+Na-2H]-234.332859911
AllCCS[M+HCOO]-238.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LactucaxanthinC\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/[C@H]1C(C)=C[C@H](O)CC1(C)C6073.2Standard polar33892256
LactucaxanthinC\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/[C@H]1C(C)=C[C@H](O)CC1(C)C4626.6Standard non polar33892256
LactucaxanthinC\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/[C@H]1C(C)=C[C@H](O)CC1(C)C4346.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lactucaxanthin,1TMS,isomer #1CC1=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/[C@H]1C(C)=C[C@H](O[Si](C)(C)C)CC1(C)C4774.3Semi standard non polar33892256
Lactucaxanthin,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/[C@H]1C(C)=C[C@H](O[Si](C)(C)C)CC1(C)C4746.3Semi standard non polar33892256
Lactucaxanthin,1TBDMS,isomer #1CC1=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/[C@H]1C(C)=C[C@H](O[Si](C)(C)C(C)(C)C)CC1(C)C4977.8Semi standard non polar33892256
Lactucaxanthin,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/[C@H]1C(C)=C[C@H](O[Si](C)(C)C(C)(C)C)CC1(C)C5202.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lactucaxanthin GC-MS (1 TMS) - 70eV, Positivesplash10-004i-3100029000-0177f8208fce473bb6aa2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lactucaxanthin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3100190000-3b2c052d1ef9e5d4be0a2017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lactucaxanthin GC-MS ("Lactucaxanthin,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lactucaxanthin GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lactucaxanthin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lactucaxanthin 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 - Lactucaxanthin 10V, Positive-QTOFsplash10-0gb9-0101190000-5985ef12ae8dca4d83f22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucaxanthin 20V, Positive-QTOFsplash10-0frt-0719740000-cde5943fb9c3e4fe9f9e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucaxanthin 40V, Positive-QTOFsplash10-0002-1449630000-1f7481e3eb567c876c852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucaxanthin 10V, Negative-QTOFsplash10-014i-0000090000-c3a0b350154f8c6bf6182016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucaxanthin 20V, Negative-QTOFsplash10-014i-0000090000-fc5067576c09502ec0d52016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucaxanthin 40V, Negative-QTOFsplash10-0udr-0522590000-a661bbd8ee97008407a62016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucaxanthin 10V, Positive-QTOFsplash10-0fri-0131930000-1b4a9df72b953b7c578c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucaxanthin 20V, Positive-QTOFsplash10-0f8c-0113920000-35ba818f2f9495497b112021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucaxanthin 40V, Positive-QTOFsplash10-0wmr-0179400000-e432857c73a24a909aab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucaxanthin 10V, Negative-QTOFsplash10-014i-0202090000-e7ff503087b0472872342021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucaxanthin 20V, Negative-QTOFsplash10-014i-0405490000-354e2648d408d044dc172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lactucaxanthin 40V, Negative-QTOFsplash10-020a-0419300000-f98a6fa25c8795ec10192021-09-22Wishart 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 IDFDB001534
KNApSAcK IDC00003775
Chemspider ID4444654
KEGG Compound IDC08599
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281242
PDB IDNot Available
ChEBI ID6357
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.