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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-08 14:59:07 UTC
Update Date2023-02-21 17:18:39 UTC
HMDB IDHMDB0029185
Secondary Accession Numbers
  • HMDB29185
Metabolite Identification
Common Name5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone
Description5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone, also known as 5-[(3,4-dihydroxyphenyl)methyl]dihydro-2(3H)-furanone, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Based on a literature review very few articles have been published on 5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone.
Structure
Data?1676999919
Synonyms
ValueSource
5-(3',4'-Dihydroxyphenyl)-g-valerolactoneGenerator
5-(3',4'-Dihydroxyphenyl)-γ-valerolactoneGenerator
(5R)-5-[(3,4-Dihydroxyphenyl)methyl]dihydro-2(3H)-furanoneHMDB
(±)-delta-(3,4-dihydroxyphenyl)-gamma-valerolactoneHMDB
(±)-δ-(3,4-dihydroxyphenyl)-γ-valerolactoneHMDB
5-(3’,4’-dihydroxyphenyl)-γ-valerolactoneHMDB
5-[(3,4-Dihydroxyphenyl)methyl]dihydro-2(3H)-furanoneHMDB
delta-(3,4-Dihydroxyphenyl)-gamma-valerolactoneHMDB
Δ-(3,4-dihydroxyphenyl)-γ-valerolactoneHMDB
5-(3',4'-Dihydroxyphenyl)-gamma-valerolactoneHMDB
5-[(3,4-Dihydroxyphenyl)methyl]oxolan-2-oneHMDB
5-(3,4-Dihydroxyphenyl)-gamma-valerolactoneHMDB
5-(Dihydroxyphenyl)-gamma-valerolactoneHMDB
5-(Dihydroxyphenyl)-valerolactoneHMDB
Chemical FormulaC11H12O4
Average Molecular Weight208.213
Monoisotopic Molecular Weight208.073558866
IUPAC Name(5R)-5-[(3,4-dihydroxyphenyl)methyl]oxolan-2-one
Traditional Name(5R)-5-[(3,4-dihydroxyphenyl)methyl]oxolan-2-one
CAS Registry Number191666-22-5
SMILES
OC1=C(O)C=C(C[C@H]2CCC(=O)O2)C=C1
InChI Identifier
InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2/t8-/m1/s1
InChI KeyZNXXWTPQHVLMQT-MRVPVSSYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Gamma butyrolactone
  • Oxolane
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility1.38 g/LALOGPS
logP1.47ALOGPS
logP1.62ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity53.31 m³·mol⁻¹ChemAxon
Polarizability20.72 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
DeepCCS[M+H]+149.66730932474
DeepCCS[M-H]-147.27130932474
DeepCCS[M-2H]-180.39930932474
DeepCCS[M+Na]+155.60630932474
AllCCS[M+H]+147.932859911
AllCCS[M+H-H2O]+143.832859911
AllCCS[M+NH4]+151.732859911
AllCCS[M+Na]+152.732859911
AllCCS[M-H]-147.632859911
AllCCS[M+Na-2H]-147.832859911
AllCCS[M+HCOO]-148.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-(3',4'-Dihydroxyphenyl)-gamma-valerolactoneOC1=C(O)C=C(C[C@H]2CCC(=O)O2)C=C13518.5Standard polar33892256
5-(3',4'-Dihydroxyphenyl)-gamma-valerolactoneOC1=C(O)C=C(C[C@H]2CCC(=O)O2)C=C12110.3Standard non polar33892256
5-(3',4'-Dihydroxyphenyl)-gamma-valerolactoneOC1=C(O)C=C(C[C@H]2CCC(=O)O2)C=C12211.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(C[C@H]2CCC(=O)O2)C=C1O2063.2Semi standard non polar33892256
5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone,1TMS,isomer #2C[Si](C)(C)OC1=CC(C[C@H]2CCC(=O)O2)=CC=C1O2045.3Semi standard non polar33892256
5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(C[C@H]2CCC(=O)O2)C=C1O[Si](C)(C)C2137.3Semi standard non polar33892256
5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H]2CCC(=O)O2)C=C1O2332.1Semi standard non polar33892256
5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(C[C@H]2CCC(=O)O2)=CC=C1O2312.8Semi standard non polar33892256
5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H]2CCC(=O)O2)C=C1O[Si](C)(C)C(C)(C)C2594.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-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'-Dihydroxyphenyl)-gamma-valerolactone 10V, Positive-QTOFsplash10-0a4i-5690000000-426cef4dbeb10dafeeae2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone 20V, Positive-QTOFsplash10-05fs-7900000000-608cd683d3b6dda831d12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone 40V, Positive-QTOFsplash10-066v-9600000000-33bdad61d6a30e899f6f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone 10V, Negative-QTOFsplash10-0a4i-1490000000-ec828d89aebc8ed026a42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone 20V, Negative-QTOFsplash10-0019-9500000000-a59c0f26c2f4508f2c4e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone 40V, Negative-QTOFsplash10-0076-6900000000-6b3eed581075ea184a372021-09-22Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 983 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 983 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 983 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 983 details
FecesDetected and Quantified1.873 +/- 3.170 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified57.634 +/- 56.673 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified12.679 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 983 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 983 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 983 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 983 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031342
KNApSAcK IDNot Available
Chemspider ID24207288
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound45093080
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. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone → 5'-(3'-Methoxy-4'-hydroxyphenyl)-gamma-valerolactonedetails
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'-Dihydroxyphenyl)-gamma-valerolactone → 3,4,5-trihydroxy-6-{2-hydroxy-4-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-2-carboxylic aciddetails
5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone → 3,4,5-trihydroxy-6-{2-hydroxy-5-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-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'-Dihydroxyphenyl)-gamma-valerolactone → 5'-(3',4'-Dihydroxyphenyl)-gamma-valerolactone sulfatedetails