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Record Information
Version4.0
Creation Date2006-05-22 14:17:53 UTC
Update Date2017-09-27 08:24:16 UTC
HMDB IDHMDB0002432
Secondary Accession Numbers
  • HMDB02432
Metabolite Identification
Common NameSumiki's acid
DescriptionSumiki's acid is a naturally occurring human metabolite. (PMID: 949837 ) Sumiki's acid was first identified in the urine of a leukemic patient who was excreting an abnormal amount of its glycine derivative. (PMID: 5043270 ). Sumiki's acid was found to be excreted by normal subjects after a Phenylalanine loading, while heterozygotes for phenylketonuria don't excrete it (instead, they excrete 2-Hydroxybenzeneacetic acid). (PMID: 4708049 ). Patients receiving furan-containing sugar solutions i.v. convert 50% of the 5-hydroxymethyl-2-furfural into Sumiki's acid. (PMID: 4202014 ).
Structure
Thumb
Synonyms
ValueSource
5-(Hydroxymethyl)-2-furoic acidChEBI
5-Hydroxymethyl-2-furancarboxylic acidChEBI
5-Hydroxymethyl-furan-2-carboxylic acidChEBI
5-Hydroxymethylfuran-2-carboxylic acidChEBI
5-Hydroxymethylfuranoic acidChEBI
5-Hydroxymethylfuroic acidChEBI
5-(Hydroxymethyl)-2-furoateGenerator
5-Hydroxymethyl-2-furancarboxylateGenerator
5-Hydroxymethyl-furan-2-carboxylateGenerator
5-Hydroxymethylfuran-2-carboxylateGenerator
5-HydroxymethylfuranoateGenerator
5-HydroxymethylfuroateGenerator
5-(Hydroxymethyl)- 2-furancarboxylateHMDB
5-Hydroxymethyl-2-furoateHMDB
5-Hydroxymethyl-2-furoic acidHMDB
HMFA compoundMeSH
Chemical FormulaC6H6O4
Average Molecular Weight142.1094
Monoisotopic Molecular Weight142.02660868
IUPAC Name5-(hydroxymethyl)furan-2-carboxylic acid
Traditional Name5-hydroxymethyl-2-furoic acid
CAS Registry Number6338-41-6
SMILES
OCC1=CC=C(O1)C(O)=O
InChI Identifier
InChI=1S/C6H6O4/c7-3-4-1-2-5(10-4)6(8)9/h1-2,7H,3H2,(H,8,9)
InChI KeyPCSKKIUURRTAEM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as furoic acids. These are organic compounds containing a furoic acid moiety, with a structure characterized by a furan ring bearing a carboxylic acid group at the C2 or C3 carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassFurans
Direct ParentFuroic acids
Alternative Parents
Substituents
  • Furoic acid
  • Heteroaromatic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility30.9 g/LALOGPS
logP0.11ALOGPS
logP-0.16ChemAxon
logS-0.66ALOGPS
pKa (Strongest Acidic)3.11ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.4 m³·mol⁻¹ChemAxon
Polarizability13.01 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0900000000-08804dfdee64d8fdccb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-4900000000-0c060367d722922909bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-9100000000-d9e22985d8ab441a9070View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-f7fb16cac73dc48ebe68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dm-8900000000-0798d45e72bf3baf92a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gi0-9000000000-9c924e2e07dc848090b6View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified9.143 +/- 4.737 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified3.2 (0.9-44.0) umol/mmol creatinineChildren (1-13 years old)Both
    Normal
    details
    UrineDetected and Quantified7.3 (0.8-26.1) umol/mmol creatinineAdolescent (13-18 years old)Both
    Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified15.1(1.4-28.8) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
    UrineDetected and Quantified12.2 (0.9-34.4) umol/mmol creatinineChildren (1-13 years old)Both
    Normal
    details
    UrineDetected and Quantified1.7 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified1.6 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified7.185 +/- 5.965 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified8.298 +/- 6.579 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Gastroesophageal reflux disease
      • Mordechai, Hien, ...
    details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB023004
    KNApSAcK IDNot Available
    Chemspider ID72827
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID6680
    PubChem Compound80642
    PDB IDNot Available
    ChEBI ID563718
    References
    Synthesis ReferenceShmagina, N. N.; Moshkin, P. A. Preparation of 5-hydroxymethyl-2-furoic acid and its butyl ester. Plasticheskie Massy (1964), (2), 51-2.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Lawson AM, Chalmers RA, Watts RW: Urinary organic acids in man. I. Normal patterns. Clin Chem. 1976 Aug;22(8):1283-7. [PubMed:949837 ]
    2. Mrochek JE, Rainey WT Jr: Identification and biochemical significance of substituted furans in human urine. Clin Chem. 1972 Aug;18(8):821-8. [PubMed:5043270 ]
    3. Blau K, Summer GK, Newsome HC, Edwards CH: Phenylalanine loading and aromatic acid excretion in normal subjects and heterozygotes for phenylketonuria. Clin Chim Acta. 1973 May 18;45(3):197-205. [PubMed:4708049 ]
    4. Jellum E, Borresen HC, Eldjarn L: The presence of furan derivatives in patients receiving fructose-containing solutions intravenously. Clin Chim Acta. 1973 Aug 30;47(2):191-201. [PubMed:4202014 ]