Np mrd loader

Showing NP-Card for 2-Furoylglycine (NP0000165)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:13:21 UTC
NP-MRD IDNP0000165
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Furoylglycine
Description2-Furoylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) Which is an enzyme that catalyzes the chemical reaction:. Acyl-CoA + glycine < -- > CoA + N-acylglycine. Dietary studies show that 2-Furoylglycine precursors are of exogenous origin. Most probably from furan derivatives found in food prepared by strong heating. This may explain the absence of 2-furoylglycine in urine of breastfed children (PMID 4630229 ).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000165 (2-Furoylglycine)


  Mrv1652305261923532D          

 12 12  0  0  0  0            999 V2000
   -0.4756    1.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8881    1.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3361    2.3716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4176    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314    1.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321    3.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8465    2.0361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9899    2.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755    1.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0000165 (2-Furoylglycine)

HMDB0000439
     RDKit          3D
2-Furoylglycine
 19 19  0  0  0  0  0  0  0  0999 V2000
   -1.8529    1.7581    0.8734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5771    1.3360   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8939    1.7691   -0.1485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0522    0.3709   -1.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6725    0.0823   -0.6841 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2894   -0.4757    0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148   -0.7583    1.4632 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169   -0.7348    0.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1667   -0.4856   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3048   -0.8806    0.5801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9420   -1.3521    1.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6565   -1.2429    1.8944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0734    2.7249   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333   -0.5770   -1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0848    0.8286   -2.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0758    0.2881   -1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626   -0.0584   -1.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3132   -0.8423    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6057   -1.7503    2.5998 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0000165 (2-Furoylglycine)


  Mrv1652305261923532D          

 12 12  0  0  0  0            999 V2000
   -0.4756    1.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8881    1.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3361    2.3716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4176    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314    1.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321    3.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8465    2.0361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9899    2.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755    1.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000165

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CNC(=O)C1=CC=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO4/c9-6(10)4-8-7(11)5-2-1-3-12-5/h1-3H,4H2,(H,8,11)(H,9,10)

> <INCHI_KEY>
KSPQDMRTZZYQLM-UHFFFAOYSA-N

> <FORMULA>
C7H7NO4

> <MOLECULAR_WEIGHT>
169.1348

> <EXACT_MASS>
169.037507717

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.3590501230494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(furan-2-yl)formamido]acetic acid

> <ALOGPS_LOGP>
0.10

> <JCHEM_LOGP>
-0.4142078716666666

> <ALOGPS_LOGS>
-1.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.098908011041576

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.342943262402008

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9694270763558905

> <JCHEM_POLAR_SURFACE_AREA>
79.53999999999999

> <JCHEM_REFRACTIVITY>
38.5086

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
furoylglycine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000165 (2-Furoylglycine)

HMDB0000439
     RDKit          3D
2-Furoylglycine
 19 19  0  0  0  0  0  0  0  0999 V2000
   -1.8529    1.7581    0.8734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5771    1.3360   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8939    1.7691   -0.1485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0522    0.3709   -1.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6725    0.0823   -0.6841 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2894   -0.4757    0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148   -0.7583    1.4632 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169   -0.7348    0.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1667   -0.4856   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3048   -0.8806    0.5801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9420   -1.3521    1.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6565   -1.2429    1.8944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0734    2.7249   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333   -0.5770   -1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0848    0.8286   -2.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0758    0.2881   -1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626   -0.0584   -1.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3132   -0.8423    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6057   -1.7503    2.5998 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

PDB for NP0000165 (2-Furoylglycine)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.888   1.949   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.658   3.283   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.627   4.427   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.780   3.801   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.619   2.269   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.113   4.571   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.113   6.111   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       3.447   3.801   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.781   4.571   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.114   3.801   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.448   4.571   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.114   2.261   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
Download

3D PDB for NP0000165 (2-Furoylglycine)

COMPND    HMDB0000439
HETATM    1  O1  UNL     1      -1.853   1.758   0.873  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.577   1.336  -0.037  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.894   1.769  -0.149  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.052   0.371  -1.013  1.00  0.00           C  
HETATM    5  N1  UNL     1      -0.673   0.082  -0.684  1.00  0.00           N  
HETATM    6  C3  UNL     1      -0.289  -0.476   0.561  1.00  0.00           C  
HETATM    7  O3  UNL     1      -1.115  -0.758   1.463  1.00  0.00           O  
HETATM    8  C4  UNL     1       1.117  -0.735   0.812  1.00  0.00           C  
HETATM    9  C5  UNL     1       2.167  -0.486  -0.070  1.00  0.00           C  
HETATM   10  C6  UNL     1       3.305  -0.881   0.580  1.00  0.00           C  
HETATM   11  C7  UNL     1       2.942  -1.352   1.815  1.00  0.00           C  
HETATM   12  O4  UNL     1       1.656  -1.243   1.894  1.00  0.00           O  
HETATM   13  H1  UNL     1      -4.073   2.725  -0.421  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.633  -0.577  -1.035  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.085   0.829  -2.010  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.076   0.288  -1.381  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.063  -0.058  -1.074  1.00  0.00           H  
HETATM   18  H6  UNL     1       4.313  -0.842   0.219  1.00  0.00           H  
HETATM   19  H7  UNL     1       3.606  -1.750   2.600  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5   14   15
CONECT    5    6   16
CONECT    6    7    7    8
CONECT    8    9    9   12
CONECT    9   10   17
CONECT   10   11   11   18
CONECT   11   12   19
END
Download

SMILES for NP0000165 (2-Furoylglycine)

OC(=O)CNC(=O)C1=CC=CO1
Download

INCHI for NP0000165 (2-Furoylglycine)

InChI=1S/C7H7NO4/c9-6(10)4-8-7(11)5-2-1-3-12-5/h1-3H,4H2,(H,8,11)(H,9,10)
Download
View in JSmol
Synonyms
ValueSource
FuroylglycineHMDB
N-(2-Furoyl)glycineHMDB
FurfuroylglycineHMDB
N-(2-Furanylcarbonyl)glycineHMDB
N-(Carboxymethyl)-2-furancarboxamideHMDB
N-2-Furoyl-glycineHMDB
PyromucurateHMDB
Pyromucuric acidHMDB
[[(Furan-2-yl)carbonyl]amino]acetateHMDB
[[(Furan-2-yl)carbonyl]amino]acetic acidHMDB
Chemical FormulaC7H7NO4
Average Mass169.1348 Da
Monoisotopic Mass169.03751 Da
IUPAC Name2-[(furan-2-yl)formamido]acetic acid
Traditional Namefuroylglycine
CAS Registry Number5657-19-2
SMILES
OC(=O)CNC(=O)C1=CC=CO1
InChI Identifier
InChI=1S/C7H7NO4/c9-6(10)4-8-7(11)5-2-1-3-12-5/h1-3H,4H2,(H,8,11)(H,9,10)
InChI KeyKSPQDMRTZZYQLM-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 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
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
Homo sapiens (Urine)Animalia
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • 2-heteroaryl carboxamide
  • Furoic acid or derivatives
  • Furan
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point163 - 165 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility31.7 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.76 g/LALOGPS
logP0.1ALOGPS
logP-0.41ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.34ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.54 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.51 m³·mol⁻¹ChemAxon
Polarizability15.36 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000439
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022046
KNApSAcK IDC00052115
Chemspider ID20549
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5428
PubChem Compound21863
PDB IDNot Available
ChEBI ID82912
Good Scents IDNot Available
References
General References
  1. Pettersen JE, Jellum E: The identification and metabolic origin of 2-furoylglycine and 2,5-furandicarboxylic acid in human urine. Clin Chim Acta. 1972 Oct;41:199-207. [PubMed:4630229 ]
  2. Xi M, Berendsen AAM, Ernst M, Hu T, Vazquez-Manjarrez N, Feskens EJM, Dragsted LO, La Barbera G: Combined Urinary Biomarkers to Assess Coffee Intake Using Untargeted Metabolomics: Discovery in Three Pilot Human Intervention Studies and Validation in Cross-Sectional Studies. J Agric Food Chem. 2021 Jun 30;69(25):7230-7242. doi: 10.1021/acs.jafc.1c01155. Epub 2021 Jun 18. [PubMed:34143629 ]
  3. Bhandari D, McCarthy D, Biren C, Movassaghi C, Blount BC, De Jesus VR: Development of a UPLC-ESI-MS/MS method to measure urinary metabolites of selected VOCs: Benzene, cyanide, furfural, furfuryl alcohol, 5-hydroxymethylfurfural, and N-methyl-2-pyrrolidone. J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Sep 15;1126-1127:121746. doi: 10.1016/j.jchromb.2019.121746. Epub 2019 Aug 14. [PubMed:31454719 ]
  4. Radjursoga M, Karlsson GB, Lindqvist HM, Pedersen A, Persson C, Pinto RC, Ellegard L, Winkvist A: Metabolic profiles from two different breakfast meals characterized by (1)H NMR-based metabolomics. Food Chem. 2017 Sep 15;231:267-274. doi: 10.1016/j.foodchem.2017.03.142. Epub 2017 Mar 27. [PubMed:28450006 ]
  5. Heinzmann SS, Holmes E, Kochhar S, Nicholson JK, Schmitt-Kopplin P: Correction to 2-Furoylglycine as a Candidate Biomarker of Coffee Consumption. J Agric Food Chem. 2016 Nov 23;64(46):8958. doi: 10.1021/acs.jafc.6b04833. Epub 2016 Nov 11. [PubMed:27934290 ]