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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 20:05:21 UTC

Update Date

2022-09-22 18:34:44 UTC

HMDB ID

HMDB0341271

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-hydroxyphenylacetylglutamine

Description

Structure

MOL SDF PDB SMILES InChI

  Mrv1652305221921252D          

 20 20  0  0  0  0            999 V2000
   -0.0513    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1763    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4638    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9388    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7013    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0112    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4138    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4138    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9388    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  6  5  1  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  8  7  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14 10  1  4  0  0  0
 14 11  2  0  0  0  0
 15  9  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  2  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 20 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341271

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCC(N=C(O)CC1=CC=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H15NO6/c15-9-3-1-8(2-4-9)7-11(16)14-10(13(19)20)5-6-12(17)18/h1-4,10,15H,5-7H2,(H,14,16)(H,17,18)(H,19,20)

> <INCHI_KEY>
CYRKYXZJUIBBJX-UHFFFAOYSA-N

> <FORMULA>
C13H15NO6

> <MOLECULAR_WEIGHT>
281.2613

> <EXACT_MASS>
281.089937217

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.193697192950857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}pentanedioic acid

> <ALOGPS_LOGP>
0.37

> <JCHEM_LOGP>
1.2373632083333332

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.129724208118086

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3611889204883614

> <JCHEM_PKA_STRONGEST_BASIC>
0.8340215693838346

> <JCHEM_POLAR_SURFACE_AREA>
127.42000000000003

> <JCHEM_REFRACTIVITY>
67.956

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}pentanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.096   4.977   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.096   7.645   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.444   4.977   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.444   7.645   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.026   3.644   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.796   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.406   6.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.866   6.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.214   6.311   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.486   3.644   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.176   4.977   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.716   2.310   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -4.716   4.977   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       3.754   6.311   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.406   3.644   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0     -10.106   0.976   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0     -10.106   3.644   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.176   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.486   0.976   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5    6   10                                                       
CONECT    6    5   12                                                       
CONECT    7    8   11                                                       
CONECT    8    1    2    7                                                  
CONECT    9    3    4   15                                                  
CONECT   10    5   13   14                                                  
CONECT   11    7   14   16                                                  
CONECT   12    6   17   18                                                  
CONECT   13   10   19   20                                                  
CONECT   14   10   11                                                       
CONECT   15    9                                                            
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   13                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxyphenylacetylglutamate	ChEBI
4-Hydroxyphenylacetylglutamic acid	ChEBI
p-Hydroxyphenylacetylglutamate	ChEBI
p-Hydroxyphenylacetylglutamic acid	ChEBI
P-Hydroxyphenylacetylglutamine	HMDB

Chemical Formula

C₁₃H₁₅NO₆

Average Molecular Weight

281.2613

Monoisotopic Molecular Weight

281.089937217

IUPAC Name

2-{[1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}pentanedioic acid

Traditional Name

2-{[1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}pentanedioic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCC(N=C(O)CC1=CC=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C13H15NO6/c15-9-3-1-8(2-4-9)7-11(16)14-10(13(19)20)5-6-12(17)18/h1-4,10,15H,5-7H2,(H,14,16)(H,17,18)(H,19,20)

InChI Key

CYRKYXZJUIBBJX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Phenylacetamide
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acylglutamic acid (CHEBI:28036 )

Ontology

Not Available

Exogenous (HMDB: HMDB06061)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.37	ALOGPS
logP	1.24	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	0.83	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	127.42 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	67.96 m³·mol⁻¹	ChemAxon
Polarizability	27.19 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-hydroxyphenylacetylglutamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-1920000000-1fa0b634b4ab989c676b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-hydroxyphenylacetylglutamine GC-MS (3 TMS) - 70eV, Positive	splash10-003r-3928400000-5d863a8ca7761728fc85	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyphenylacetylglutamine 10V, Negative-QTOF	splash10-001i-0090000000-3286bc974a189b026e7a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyphenylacetylglutamine 20V, Negative-QTOF	splash10-01qi-0980000000-d240fae32f133162a333	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyphenylacetylglutamine 40V, Negative-QTOF	splash10-0zi3-5900000000-def93d56b16fcccc7678	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyphenylacetylglutamine 10V, Positive-QTOF	splash10-03e9-0390000000-6d4c885b6c839ca27fac	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyphenylacetylglutamine 20V, Positive-QTOF	splash10-0ka9-0930000000-db475847e7cc2c9f1ad1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyphenylacetylglutamine 40V, Positive-QTOF	splash10-0kdi-7900000000-43df9129e7aae30c92fa	2017-09-01	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023825

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05595

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440731

PDB ID

Not Available

ChEBI ID

28036

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]

Showing metabocard for 4-hydroxyphenylacetylglutamine (HMDB0341271)

MOL for HMDB0341271 (4-hydroxyphenylacetylglutamine)

3D MOL for HMDB0341271 (4-hydroxyphenylacetylglutamine)

3D SDF for HMDB0341271 (4-hydroxyphenylacetylglutamine)

3D-SDF for HMDB0341271 (4-hydroxyphenylacetylglutamine)

PDB for HMDB0341271 (4-hydroxyphenylacetylglutamine)

3D PDB for HMDB0341271 (4-hydroxyphenylacetylglutamine)

SMILES for HMDB0341271 (4-hydroxyphenylacetylglutamine)

INCHI for HMDB0341271 (4-hydroxyphenylacetylglutamine)

Structure for HMDB0341271 (4-hydroxyphenylacetylglutamine)

3D Structure for HMDB0341271 (4-hydroxyphenylacetylglutamine)

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra