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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:53 UTC
Update Date2019-07-23 05:45:32 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?1563860732
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
Sumiki's acidChEBI
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
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00vm-9500000000-b2d1e3aaf404151d4d9dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-9840000000-336219774bf0ad330848JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0900000000-08804dfdee64d8fdccb2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-4900000000-0c060367d722922909bfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-9100000000-d9e22985d8ab441a9070JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-f7fb16cac73dc48ebe68JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dm-8900000000-0798d45e72bf3baf92a0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gi0-9000000000-9c924e2e07dc848090b6JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    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
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>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 Quantified Adult (>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
    FoodDB 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
    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 ]