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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-12 03:36:37 UTC
Update Date2022-03-07 02:57:08 UTC
HMDB IDHMDB0041691
Secondary Accession Numbers
  • HMDB41691
Metabolite Identification
Common Name5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone
Description5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone belongs to the class of organic compounds known as pyrogallols and derivatives. Pyrogallols and derivatives are compounds containing a 1,2,3-trihydroxybenzene moiety. 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone.
Structure
Data?1563863691
Synonyms
ValueSource
5-(3',4',5'-Trihydroxyphenyl)-g-valerolactoneGenerator
5-(3',4',5'-Trihydroxyphenyl)-γ-valerolactoneGenerator
Chemical FormulaC11H12O5
Average Molecular Weight224.21
Monoisotopic Molecular Weight224.068473494
IUPAC Name5-[(3,4,5-trihydroxyphenyl)methyl]oxolan-2-one
Traditional Name5-[(3,4,5-trihydroxyphenyl)methyl]oxolan-2-one
CAS Registry NumberNot Available
SMILES
OC1=CC(CC2CCC(=O)O2)=CC(O)=C1O
InChI Identifier
InChI=1S/C11H12O5/c12-8-4-6(5-9(13)11(8)15)3-7-1-2-10(14)16-7/h4-5,7,12-13,15H,1-3H2
InChI KeyCZVAQLJEUUFQCH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrogallols and derivatives. Pyrogallols and derivatives are compounds containing a 1,2,3-trihydroxybenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenetriols and derivatives
Direct ParentPyrogallols and derivatives
Alternative Parents
Substituents
  • Pyrogallol derivative
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
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 Solubility1.94 g/LALOGPS
logP1.18ALOGPS
logP1.31ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)8.89ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55.29 m³·mol⁻¹ChemAxon
Polarizability21.64 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
DarkChem[M+H]+152.54631661259
DarkChem[M-H]-151.23831661259
DeepCCS[M+H]+149.52930932474
DeepCCS[M-H]-147.17130932474
DeepCCS[M-2H]-181.62530932474
DeepCCS[M+Na]+156.09630932474
AllCCS[M+H]+150.932859911
AllCCS[M+H-H2O]+146.832859911
AllCCS[M+NH4]+154.832859911
AllCCS[M+Na]+155.932859911
AllCCS[M-H]-150.332859911
AllCCS[M+Na-2H]-150.432859911
AllCCS[M+HCOO]-150.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactoneOC1=CC(CC2CCC(=O)O2)=CC(O)=C1O3813.3Standard polar33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactoneOC1=CC(CC2CCC(=O)O2)=CC(O)=C1O2334.7Standard non polar33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactoneOC1=CC(CC2CCC(=O)O2)=CC(O)=C1O2452.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,1TMS,isomer #1C[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O)=C1O2229.9Semi standard non polar33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,1TMS,isomer #2C[Si](C)(C)OC1=C(O)C=C(CC2CCC(=O)O2)C=C1O2229.6Semi standard non polar33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,2TMS,isomer #1C[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C)=C1O2260.0Semi standard non polar33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,2TMS,isomer #2C[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O)=C1O[Si](C)(C)C2268.8Semi standard non polar33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,3TMS,isomer #1C[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C2314.8Semi standard non polar33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O)=C1O2514.1Semi standard non polar33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C(O)C=C(CC2CCC(=O)O2)C=C1O2513.1Semi standard non polar33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C(C)(C)C)=C1O2790.2Semi standard non polar33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O)=C1O[Si](C)(C)C(C)(C)C2758.5Semi standard non polar33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C3020.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fbi-4900000000-aa407ce8b928271224352017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone GC-MS (3 TMS) - 70eV, Positivesplash10-00us-4009100000-3c85a877af2785527a372017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 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 - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 10V, Positive-QTOFsplash10-004i-0390000000-005c046b64fa400546ea2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 20V, Positive-QTOFsplash10-004r-2920000000-3da2123cba34d8e561f82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 40V, Positive-QTOFsplash10-000i-9800000000-4d0ddda730f3f457928c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 10V, Negative-QTOFsplash10-00di-0290000000-ca50e6c2cd8c6aed9f932017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 20V, Negative-QTOFsplash10-00fs-2970000000-91fdf1beca5ad48fa42f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 40V, Negative-QTOFsplash10-004l-7900000000-06a574a6947ca4bd6f672017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 10V, Positive-QTOFsplash10-004u-1950000000-176b5d1849bbdc3eaa1f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 20V, Positive-QTOFsplash10-05a9-4910000000-3bce2f7fdb3f916695a02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 40V, Positive-QTOFsplash10-05o9-9600000000-dbc584e157afb6b9dbed2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 10V, Negative-QTOFsplash10-00di-1690000000-fbe999d62045de96f6ee2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 20V, Negative-QTOFsplash10-0f7t-8910000000-8bd6afb0fb725a6e3ec62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone 40V, Negative-QTOFsplash10-0fk9-6900000000-a243697def0606ce40ee2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 984 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 984 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 984 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 984 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029854
KNApSAcK IDNot Available
Chemspider ID21233624
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44389277
PDB IDNot Available
ChEBI ID134255
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. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone → 6-{2,3-dihydroxy-5-[(5-oxooxolan-2-yl)methyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone → 6-{2,6-dihydroxy-4-[(5-oxooxolan-2-yl)methyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone → 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphatedetails