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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:53 UTC
Update Date2020-02-26 21:24:09 UTC
HMDB IDHMDB0002432
Secondary Accession Numbers
  • HMDB0029188
  • HMDB02432
  • HMDB29188
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 ). Sumiki's acid has been found to be a byproduct of the fungus Aspergillus and probably other species of fungi and yeast as well (http://drweyrich.weyrich.com/labs/oat.html).
Structure
Data?1582752249
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-furoic acidKegg
5-(Hydroxymethyl)-2-furoateGenerator
5-Hydroxymethyl-2-furancarboxylateGenerator
5-Hydroxymethyl-furan-2-carboxylateGenerator
5-Hydroxymethylfuran-2-carboxylateGenerator
5-HydroxymethylfuranoateGenerator
5-HydroxymethylfuroateGenerator
5-Hydroxymethyl-2-furoateGenerator
5-(Hydroxymethyl)- 2-furancarboxylateHMDB
HMFA compoundHMDB
2-(Hydroxymethyl)furan-5-carboxylic acidHMDB
5-(Hydroxymethyl)-2-furancarboxylic acidHMDB
5-Hydroxymethyl-2-furanoateHMDB
5-Hydroxymethyl-2-furanoic acidHMDB
Sumikis' acidHMDB
Sumikis’ acidHMDB
Sumiki’s acidHMDB
Sumiki's acidChEBI
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
Description belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurans
Sub ClassFuroic acid and derivatives
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

Source:

Biological location:

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)-6.6ChemAxon
pKa (Strongest Basic)6.42ChemAxon
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00vm-9500000000-b2d1e3aaf404151d4d9dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-9840000000-336219774bf0ad330848Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0006-0900000000-e5e4c9ab22ecc0c03127Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0006-1900000000-f0510b9694865db5b8a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0006-2900000000-2b9147f983aabe5f4bceSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0006-3900000000-5edfe3cceba737b695bbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0006-5900000000-2bbe5a106406837f9715Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0007-9700000000-4860ecd2a9e902ab9019Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0005-9500000000-9a092fe26e7cb22bb011Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0005-9400000000-2ce66457ed8632da68ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9200000000-fa8f72b72bb2d33bae17Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-00kb-9000000000-14d9ae43c6246fb6bef6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-00kb-9000000000-eba6fe49d9507453bd44Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-014j-9000000000-9eaaaaf4c5e8684ba8c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-014j-9000000000-2990c55614ca2d807fb8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-014i-9000000000-b488c1f5e67f424a4c6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 9V, negativesplash10-0002-9000000000-381873a57e49d091f23dSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 9V, negativesplash10-014i-9000000000-8694c521db85b08bb718Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0006-0900000000-878e80e3d21462667d81Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-002f-0900000000-2fc219c3ceb2b4b888adSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-004l-0900000000-87a331e5b1cada010f1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0900000000-08804dfdee64d8fdccb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-4900000000-0c060367d722922909bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-9100000000-d9e22985d8ab441a9070Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-f7fb16cac73dc48ebe68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dm-8900000000-0798d45e72bf3baf92a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gi0-9000000000-9c924e2e07dc848090b6Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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 QuantifiedAdult (>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
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
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
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023004
KNApSAcK IDNot Available
Chemspider ID72827
KEGG Compound IDC20448
BioCyc IDCPD-14103
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6680
PubChem Compound80642
PDB IDNot Available
ChEBI ID89118
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 ]