Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 01:05:38 UTC
Update Date2021-09-26 22:57:53 UTC
HMDB IDHMDB0247940
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcifran
Description5-methyl-4-oxo-5-phenyl-4,5-dihydrofuran-2-carboxylic acid, also known as reductol, belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. Based on a literature review very few articles have been published on 5-methyl-4-oxo-5-phenyl-4,5-dihydrofuran-2-carboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Acifran is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Acifran is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
ReductolKegg
5-Methyl-4-oxo-5-phenyl-4,5-dihydrofuran-2-carboxylateGenerator
2-Methyl-2-phenyl-3(2H)furanone-5-carboxylic acidMeSH
Chemical FormulaC12H10O4
Average Molecular Weight218.208
Monoisotopic Molecular Weight218.057908802
IUPAC Name5-methyl-4-oxo-5-phenyl-4,5-dihydrofuran-2-carboxylic acid
Traditional Nameacifran
CAS Registry NumberNot Available
SMILES
CC1(OC(=CC1=O)C(O)=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C12H10O4/c1-12(8-5-3-2-4-6-8)10(13)7-9(16-12)11(14)15/h2-7H,1H3,(H,14,15)
InChI KeyDFDGRKNOFOJBAJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentFuranones
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • 3-furanone
  • Benzenoid
  • Vinylogous ester
  • Ketone
  • Cyclic ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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
logP2.02ALOGPS
logP1.95ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)2.9ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity57.39 m³·mol⁻¹ChemAxon
Polarizability21.33 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]+154.49730932474
DeepCCS[M-H]-152.10230932474
DeepCCS[M-2H]-185.34930932474
DeepCCS[M+Na]+160.49630932474
AllCCS[M+H]+147.432859911
AllCCS[M+H-H2O]+143.232859911
AllCCS[M+NH4]+151.432859911
AllCCS[M+Na]+152.532859911
AllCCS[M-H]-148.532859911
AllCCS[M+Na-2H]-148.532859911
AllCCS[M+HCOO]-148.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AcifranCC1(OC(=CC1=O)C(O)=O)C1=CC=CC=C13095.9Standard polar33892256
AcifranCC1(OC(=CC1=O)C(O)=O)C1=CC=CC=C11755.5Standard non polar33892256
AcifranCC1(OC(=CC1=O)C(O)=O)C1=CC=CC=C11833.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Acifran GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udm-3900000000-3fd7c6fab0a082a382342021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acifran GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acifran GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acifran GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acifran 10V, Positive-QTOFsplash10-014i-0190000000-c95d0b923be3a12a199e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acifran 20V, Positive-QTOFsplash10-014i-2490000000-9fe492522f67d63687a72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acifran 40V, Positive-QTOFsplash10-0zfr-5900000000-927839d261a8d15d6d1c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acifran 10V, Negative-QTOFsplash10-014i-0190000000-18e16028c47e16faab6f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acifran 20V, Negative-QTOFsplash10-01b9-1980000000-2b7dbd31ffb6dbbf243f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acifran 40V, Negative-QTOFsplash10-0a6s-8900000000-1653856e95dde19477532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acifran 10V, Positive-QTOFsplash10-0ldi-0970000000-a2402138c9044ca361732021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acifran 20V, Positive-QTOFsplash10-0pb9-3900000000-846e0d1bc2525ce19f512021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acifran 40V, Positive-QTOFsplash10-0udi-8900000000-84c223239279433f1d5c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acifran 10V, Negative-QTOFsplash10-014i-0290000000-eb010b2d705c6707f7d92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acifran 20V, Negative-QTOFsplash10-0f6t-9800000000-5aca951713cd28fea79a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acifran 40V, Negative-QTOFsplash10-0fb9-9400000000-d9061c5c33d2cf0bda5a2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID46712
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Acts as a high affinity receptor for both nicotinic acid (also known as niacin) and (D)-beta-hydroxybutyrate and mediates increased adiponectin secretion and decreased lipolysis through G(i)-protein-mediated inhibition of adenylyl cyclase. This pharmacological effect requires nicotinic acid doses that are much higher than those provided by a normal diet. Mediates nicotinic acid-induced apoptosis in mature neutrophils. Receptor activation by nicotinic acid results in reduced cAMP levels which may affect activity of cAMP-dependent protein kinase A and phosphorylation of target proteins, leading to neutrophil apoptosis. The rank order of potency for the displacement of nicotinic acid binding is 5- methyl pyrazole-3-carboxylic acid = pyridine-3-acetic acid > acifran > 5-methyl nicotinic acid = acipimox >> nicotinuric acid = nicotinamide
Gene Name:
GPR109A
Uniprot ID:
Q8TDS4
Molecular weight:
41849.1