Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-07-26 11:00:16 UTC
Update Date2022-09-22 17:43:47 UTC
HMDB IDHMDB0001931
Secondary Accession Numbers
  • HMDB01931
Metabolite Identification
Common Namegamma-CEHC
Descriptiongamma-CEHC (gamma-carboxyethyl hydroxychroman) is a metabolite of vitamin E. Smokers have a significantly higher excretion level of urinary gamma-CEHC, and therefore require more vitamin E compared to non-smokers. Cigarette smoking is associated with increased oxidative stress and increased risk of degenerative disease. As the major lipophilic antioxidant, requirements for vitamin E may also be higher in smokers due to increased utilization (PMID: 15493460 ).
Structure
Data?1582752217
Synonyms
ValueSource
g-CEHCGenerator
Γ-cehcGenerator
3-(6-Hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoateHMDB
S-LLU-alphaHMDB
LLU-alphaHMDB
3-(2,7,8-Trimethyl-3,4-dihydro-2H-chromen-2-yl)propanoateHMDB
(±)-llu-αHMDB
(±)-llu-alphaHMDB
2,7,8-Trimethyl-2-(β-carboxyethyl)-6-hydroxychromanHMDB
2,7,8-Trimethyl-2-(beta-carboxyethyl)-6-hydroxychromanHMDB
γ-Carboxyethyl hydroxychromanHMDB
γ-Carboxyethyl-hydroxychromanHMDB
gamma-Carboxyethyl hydroxychromanHMDB
gamma-Carboxyethyl-hydroxychromanHMDB
3'-CarboxychromanolHMDB
gamma-CEHCMeSH
Chemical FormulaC15H20O4
Average Molecular Weight264.321
Monoisotopic Molecular Weight264.136159124
IUPAC Name3-(6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoic acid
Traditional Name3-(6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl)propanoic acid
CAS Registry Number178167-75-4
SMILES
CC1=C(O)C=C2CCC(C)(CCC(O)=O)OC2=C1C
InChI Identifier
InChI=1S/C15H20O4/c1-9-10(2)14-11(8-12(9)16)4-6-15(3,19-14)7-5-13(17)18/h8,16H,4-7H2,1-3H3,(H,17,18)
InChI KeyVMJQLPNCUPGMNQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent1-benzopyrans
Alternative Parents
Substituents
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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 Solubility0.031 g/LALOGPS
logP2.48ALOGPS
logP3.37ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.34 m³·mol⁻¹ChemAxon
Polarizability28.59 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+162.17532859911
AllCCS[M-H]-166.93932859911
DeepCCS[M+H]+161.74830932474
DeepCCS[M-H]-159.3930932474
DeepCCS[M-2H]-192.28930932474
DeepCCS[M+Na]+167.84130932474
AllCCS[M+H]+162.232859911
AllCCS[M+H-H2O]+158.532859911
AllCCS[M+NH4]+165.632859911
AllCCS[M+Na]+166.632859911
AllCCS[M-H]-166.932859911
AllCCS[M+Na-2H]-167.032859911
AllCCS[M+HCOO]-167.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
gamma-CEHCCC1=C(O)C=C2CCC(C)(CCC(O)=O)OC2=C1C3501.7Standard polar33892256
gamma-CEHCCC1=C(O)C=C2CCC(C)(CCC(O)=O)OC2=C1C2263.3Standard non polar33892256
gamma-CEHCCC1=C(O)C=C2CCC(C)(CCC(O)=O)OC2=C1C2361.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
gamma-CEHC,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C=C2CCC(C)(CCC(=O)O)OC2=C1C2314.7Semi standard non polar33892256
gamma-CEHC,1TMS,isomer #2CC1=C(O)C=C2CCC(C)(CCC(=O)O[Si](C)(C)C)OC2=C1C2243.7Semi standard non polar33892256
gamma-CEHC,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C=C2CCC(C)(CCC(=O)O[Si](C)(C)C)OC2=C1C2293.9Semi standard non polar33892256
gamma-CEHC,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C=C2CCC(C)(CCC(=O)O)OC2=C1C2577.3Semi standard non polar33892256
gamma-CEHC,1TBDMS,isomer #2CC1=C(O)C=C2CCC(C)(CCC(=O)O[Si](C)(C)C(C)(C)C)OC2=C1C2528.2Semi standard non polar33892256
gamma-CEHC,2TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C=C2CCC(C)(CCC(=O)O[Si](C)(C)C(C)(C)C)OC2=C1C2784.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - gamma-CEHC 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 - gamma-CEHC 10V, Positive-QTOFsplash10-001i-0390000000-b666254f822f684d0f902018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-CEHC 20V, Positive-QTOFsplash10-000i-2920000000-bb8603bd0385ca9852112018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-CEHC 40V, Positive-QTOFsplash10-05r9-5900000000-5e06b4301c1de7edc79a2018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-CEHC 10V, Positive-QTOFsplash10-0002-0490000000-f7808533b982dc68faac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-CEHC 20V, Positive-QTOFsplash10-0f6t-0930000000-bd68d5cb372a6bcdc8332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-CEHC 40V, Positive-QTOFsplash10-0fdk-4900000000-8472a89e5baa2c6943142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-CEHC 10V, Negative-QTOFsplash10-014i-0090000000-3a627b5dee80a85c13602021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-CEHC 20V, Negative-QTOFsplash10-014i-1290000000-91128d74296130540d8c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-CEHC 40V, Negative-QTOFsplash10-0iki-2950000000-0c65f7f58462d69265522021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.16 (0.11-0.2) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022748
KNApSAcK IDNot Available
Chemspider ID117455
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15887183
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. Jeanes YM, Hall WL, Proteggente AR, Lodge JK: Cigarette smokers have decreased lymphocyte and platelet alpha-tocopherol levels and increased excretion of the gamma-tocopherol metabolite gamma-carboxyethyl-hydroxychroman (gamma-CEHC). Free Radic Res. 2004 Aug;38(8):861-8. [PubMed:15493460 ]
  2. Galli F, Lee R, Dunster C, Kelly FJ: Gas chromatography mass spectrometry analysis of carboxyethyl-hydroxychroman metabolites of alpha- and gamma-tocopherol in human plasma. Free Radic Biol Med. 2002 Feb 15;32(4):333-40. [PubMed:11841923 ]