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Showing metabocard for Sumiki's acid (HMDB0002432)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:53 UTC
Update Date2023-02-21 17:16:23 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.
Structure
Data?1676999783
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002432 (Sumiki's acid)

  Mrv1652304272019282D          

 10 10  0  0  0  0            999 V2000
    0.7018    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718   -1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0802   -2.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1490    1.7179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889    0.5619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
M  END
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3D MOL for HMDB0002432 (Sumiki's acid)

HMDB0002432
     RDKit          3D
Sumiki's acid
 16 16  0  0  0  0  0  0  0  0999 V2000
    3.4886    0.9015    0.5281 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7293    0.0619    0.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -0.9641   -0.7105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2993    0.1937    0.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6139    1.1698    0.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7329    0.9138    0.8576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8349   -0.2271    0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1265   -0.8971   -0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277   -0.3859   -1.4522 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3622   -0.6213   -0.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9892   -1.2490   -1.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144    1.9806    1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5148    1.5108    1.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462   -1.9784   -0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8608   -0.7881    0.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2198    0.3789   -1.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  8 14  1  0
  8 15  1  0
  9 16  1  0
M  END
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3D SDF for HMDB0002432 (Sumiki's acid)

  Mrv1652304272019282D          

 10 10  0  0  0  0            999 V2000
    0.7018    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718   -1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0802   -2.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1490    1.7179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889    0.5619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002432

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C6H6O4

> <MOLECULAR_WEIGHT>
142.1094

> <EXACT_MASS>
142.02660868

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
13.011448051372877

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(hydroxymethyl)furan-2-carboxylic acid

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
-0.1562732756666666

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.819647894340136

> <JCHEM_PKA_STRONGEST_ACIDIC>
-6.610346622263484

> <JCHEM_PKA_STRONGEST_BASIC>
6.420338505376033

> <JCHEM_POLAR_SURFACE_AREA>
70.67

> <JCHEM_REFRACTIVITY>
32.3985

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.09e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxymethyl-2-furoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0002432 (Sumiki's acid)

HMDB0002432
     RDKit          3D
Sumiki's acid
 16 16  0  0  0  0  0  0  0  0999 V2000
    3.4886    0.9015    0.5281 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7293    0.0619    0.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -0.9641   -0.7105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2993    0.1937    0.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6139    1.1698    0.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7329    0.9138    0.8576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8349   -0.2271    0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1265   -0.8971   -0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277   -0.3859   -1.4522 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3622   -0.6213   -0.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9892   -1.2490   -1.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144    1.9806    1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5148    1.5108    1.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462   -1.9784   -0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8608   -0.7881    0.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2198    0.3789   -1.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  8 14  1  0
  8 15  1  0
  9 16  1  0
M  END
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PDB for HMDB0002432 (Sumiki's acid)

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.310   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.405   1.246   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.881  -2.711   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.405  -1.246   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.060   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.306   1.675   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.150  -3.855   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.145   3.207   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.713   1.049   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.060  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    5                                                       
CONECT    3    4    7                                                       
CONECT    4    1    3   10                                                  
CONECT    5    2    6   10                                                  
CONECT    6    5    8    9                                                  
CONECT    7    3                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    4    5                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0002432 (Sumiki's acid)

COMPND    HMDB0002432
HETATM    1  O1  UNL     1       3.489   0.901   0.528  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.729   0.062   0.021  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.267  -0.964  -0.710  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.299   0.194   0.218  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.614   1.170   0.927  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.733   0.914   0.858  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.835  -0.227   0.097  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.126  -0.897  -0.255  1.00  0.00           C  
HETATM    9  O3  UNL     1      -2.628  -0.386  -1.452  1.00  0.00           O  
HETATM   10  O4  UNL     1       0.362  -0.621  -0.259  1.00  0.00           O  
HETATM   11  H1  UNL     1       2.989  -1.249  -1.630  1.00  0.00           H  
HETATM   12  H2  UNL     1       1.114   1.981   1.435  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.515   1.511   1.319  1.00  0.00           H  
HETATM   14  H4  UNL     1      -1.946  -1.978  -0.408  1.00  0.00           H  
HETATM   15  H5  UNL     1      -2.861  -0.788   0.558  1.00  0.00           H  
HETATM   16  H6  UNL     1      -3.220   0.379  -1.246  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5    5   10
CONECT    5    6   12
CONECT    6    7    7   13
CONECT    7    8   10
CONECT    8    9   14   15
CONECT    9   16
END
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SMILES for HMDB0002432 (Sumiki's acid)

OCC1=CC=C(O1)C(O)=O
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INCHI for HMDB0002432 (Sumiki's acid)

InChI=1S/C6H6O4/c7-3-4-1-2-5(10-4)6(8)9/h1-2,7H,3H2,(H,8,9)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
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
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point349.40 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility227300 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.550 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
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
    • Analysis of 30 no...
 details
UrineDetected and Quantified8.298 +/- 6.579 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
 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. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023004
KNApSAcK IDC00052414
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 IDNot Available
Good Scents IDrw1059531
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 ]