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Human Metabolome Database Version 3.5

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Showing metabocard for Sumiki's acid (HMDB02432)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:53 -0600
Update Date 2013-02-08 17:11:55 -0700
HMDB ID HMDB02432
Secondary Accession Numbers None
Metabolite Identification
Common Name Sumiki's acid
Description Sumiki's acid is a naturally occurring human metabolite. (PMID: 949837 Link_out) 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 Link_out). 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 Link_out). Patients receiving furan-containing sugar solutions i.v. convert 50% of the 5-hydroxymethyl-2-furfural into Sumiki's acid. (PMID: 4202014 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 5-(Hydroxymethyl)- 2-Furancarboxylate
  2. 5-(Hydroxymethyl)-2-Furoate
  3. 5-(Hydroxymethyl)-2-Furoic acid
  4. 5-Hydroxymethyl-2-furancarboxylate
  5. 5-Hydroxymethyl-2-furancarboxylic acid
  6. 5-Hydroxymethyl-2-furoate
  7. 5-Hydroxymethyl-2-furoic acid
  8. 5-Hydroxymethyl-furan-2-carboxylate
  9. 5-Hydroxymethyl-furan-2-carboxylic acid
  10. 5-Hydroxymethylfuran-2-carboxylic acid
  11. 5-Hydroxymethylfuranoate
  12. 5-Hydroxymethylfuranoic acid
  13. 5-Hydroxymethylfuroate
  14. 5-Hydroxymethylfuroic acid
Chemical Formula C6H6O4
Average Molecular Weight 142.1094
Monoisotopic Molecular Weight 142.02660868
IUPAC Name 5-(hydroxymethyl)furan-2-carboxylic acid
Traditional IUPAC Name 5-(hydroxymethyl)furan-2-carboxylic acid
CAS Registry Number 6338-41-6
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 Key PCSKKIUURRTAEM-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteromonocyclic Compounds
Class Furans
Sub Class Furoic Acid Derivatives
Other Descriptors
  • Aromatic Heteromonocyclic Compounds
Substituents
  • Carboxylic Acid
  • Primary Alcohol
Direct Parent Furoic Acid Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 30.9 g/L ALOGPS
LogP 0.11 ALOGPS
LogP -0.16 ChemAxon
LogS -0.66 ALOGPS
pKa (strongest acidic) 3.11 ChemAxon
pKa (strongest basic) -3.4 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 70.67 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 32.4 ChemAxon
Polarizability 13.01 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
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3.2 (0.9-44.0) umol/mmol creatinine Children (1-13 year old) Both Normal Children aged 2-6 years
Urine Detected and Quantified
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7.3 (0.8-26.1) umol/mmol creatinine Adolescent (13-18 years old) Both Normal Children >10 years old
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
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15.1(1.4-28.8) umol/mmol creatinine Newborn (0-30 days old) Both Normal Not Available
Urine Detected and Quantified
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12.2 (0.9-34.4) umol/mmol creatinine Children (1-13 year old) Both Normal Children aged 6-10 years
Urine Detected and Quantified
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1.7 umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
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1.6 umol/mmol creatinine Adult (>18 years old) Both Normal by GC-MS
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023004
KNApSAcK ID Not Available
Chemspider ID 72827 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02432 Link_out
Metagene Link HMDB02432 Link_out
METLIN ID 6680 Link_out
PubChem Compound 80642 Link_out
PDB ID Not Available
ChEBI ID 563718 Link_out
References
Synthesis Reference Shmagina, 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 Not Available