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Showing NP-Card for Sumiki's acid (NP0000053)

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Record Information
Version2.0
Created at2006-05-22 14:17:53 UTC
Updated at2024-09-03 04:19:09 UTC
NP-MRD IDNP0000053
Natural Product DOIhttps://doi.org/10.57994/1651
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000053 (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
Download

3D MOL for NP0000053 (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
Download

3D SDF for NP0000053 (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>
NP0000053

> <DATABASE_NAME>
NP-MRD

> <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 NP0000053 (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
Download

PDB for NP0000053 (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
Download

3D PDB for NP0000053 (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
Download

SMILES for NP0000053 (Sumiki's acid)

OCC1=CC=C(O1)C(O)=O
Download

INCHI for NP0000053 (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 JSmol
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 Mass142.1094 Da
Monoisotopic Mass142.02661 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arthrinium arundinisLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homalomena occultaLOTUS Database
Komagataeibacter xylinusLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Rehmannia glutinosaLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Wardomyces anomalusLOTUS Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
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
Physical Properties
StateSolid
Experimental 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
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
HMDB IDHMDB0002432
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDrw1059531
References
General References