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Record Information
Version3.6
Creation Date2006-05-22 14:17:53 UTC
Update Date2016-02-11 01:05:40 UTC
HMDB IDHMDB02432
Secondary Accession NumbersNone
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 acidKegg
5-Hydroxymethyl-2-furoateGenerator
5-(Hydroxymethyl)- 2-furancarboxylateHMDB
5-(Hydroxymethyl)-2-furoateHMDB
5-(Hydroxymethyl)-2-furoic acidHMDB
5-Hydroxymethyl-2-furancarboxylateHMDB
5-Hydroxymethyl-2-furancarboxylic acidHMDB
5-Hydroxymethyl-furan-2-carboxylateHMDB
5-Hydroxymethyl-furan-2-carboxylic acidHMDB
5-Hydroxymethylfuran-2-carboxylic acidHMDB
5-HydroxymethylfuranoateHMDB
5-Hydroxymethylfuranoic acidHMDB
5-HydroxymethylfuroateHMDB
5-Hydroxymethylfuroic acidHMDB
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 KeyInChIKey=PCSKKIUURRTAEM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as furoic acid derivatives. 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurans
Sub ClassFuroic acid derivatives
Direct ParentFuroic acid derivatives
Alternative Parents
Substituents
  • Furoate
  • Heteroaromatic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.4 m3·mol-1ChemAxon
Polarizability13.01 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
FecesDetected but not QuantifiedNot ApplicableAdult (>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 QuantifiedNot ApplicableAdult (>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
NuGOwiki LinkHMDB02432
Metagene LinkHMDB02432
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. [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. [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. [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. [4202014 ]