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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:07 UTC

HMDB ID

HMDB0000735

Secondary Accession Numbers

HMDB00735

Metabolite Identification

Common Name

Hydroxyphenylacetylglycine

Description

Hydroxyphenylacetylglycine 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. Hydroxyphenylacetylglycine is an endogenous human metabolite. It can be originated from the metabolism of tyramine, itself is a monoamine compound derived from the amino acid tyrosine. Hydroxyphenylacetylglycine can also be derived from the metabolism of 3,4-dihydroxyphenylalanine (L-DOPA). In the metabolism of tyrosine, this compound is involved in the reaction Hydroxyphenylacetyl-CoA + Glycine <=> Hydroxyphenylacetylglycine + CoA, catalyzed by acyltransferase enzymes (EC 2.3.1.-). Hydroxyphenylacetylglycine has been identified in human biofluids. (PMID: 14201174 , 912020 , 716472 , 7096501 , 7438429 , 7438430 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305271900162D          

 15 15  0  0  0  0            999 V2000
   24.7578  -12.8609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3289  -16.1609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4723   -9.9734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0434   -9.9734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0434  -11.6234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3289  -12.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3289  -13.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0434  -12.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0434  -14.0984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6144  -14.0984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0434  -14.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6144  -14.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7578  -11.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3289  -15.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7578  -10.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  2  0  0  0  0
  2 14  1  0  0  0  0
  3 15  1  0  0  0  0
  4 15  2  0  0  0  0
  5  8  1  0  0  0  0
  5 13  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 14  2  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000735

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO4/c12-8-3-1-7(2-4-8)5-9(13)11-6-10(14)15/h1-4,12H,5-6H2,(H,11,13)(H,14,15)

> <INCHI_KEY>
CPPDWYIPKSSNNM-UHFFFAOYSA-N

> <FORMULA>
C10H11NO4

> <MOLECULAR_WEIGHT>
209.1986

> <EXACT_MASS>
209.068807845

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.12583774703211

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[2-(4-hydroxyphenyl)acetamido]acetic acid

> <ALOGPS_LOGP>
0.46

> <JCHEM_LOGP>
0.20214554399999995

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.497345318787255

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.538129429787069

> <JCHEM_PKA_STRONGEST_BASIC>
-2.926284978780969

> <JCHEM_POLAR_SURFACE_AREA>
86.63

> <JCHEM_REFRACTIVITY>
52.150000000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
p-hydroxyphenylacetylglycine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      46.215 -24.007   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      43.547 -30.167   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      47.548 -18.617   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      44.881 -18.617   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      44.881 -21.697   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      43.547 -24.007   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      43.547 -25.547   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      44.881 -23.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      44.881 -26.317   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      42.214 -26.317   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      44.881 -27.857   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      42.214 -27.857   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      46.215 -20.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      43.547 -28.627   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      46.215 -19.387   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5    8   13                                                       
CONECT    6    7    8                                                       
CONECT    7    6    9   10                                                  
CONECT    8    1    5    6                                                  
CONECT    9    7   11                                                       
CONECT   10    7   12                                                       
CONECT   11    9   14                                                       
CONECT   12   10   14                                                       
CONECT   13    5   15                                                       
CONECT   14    2   11   12                                                  
CONECT   15    3    4   13                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0000735
HETATM    1  O1  UNL     1       4.905  -0.149   1.131  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.483   0.176   0.032  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.990   1.426  -0.546  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.517  -0.515  -0.808  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.207   0.037  -0.845  1.00  0.00           N  
HETATM    6  C3  UNL     1       1.294   0.333   0.197  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.542   0.048   1.355  1.00  0.00           O  
HETATM    8  C4  UNL     1       0.031   1.023  -0.162  1.00  0.00           C  
HETATM    9  C5  UNL     1      -1.223   0.410   0.196  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.522  -0.904   0.406  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.807  -1.363   0.628  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.890  -0.472   0.637  1.00  0.00           C  
HETATM   13  O4  UNL     1      -5.143  -0.966   0.845  1.00  0.00           O  
HETATM   14  C9  UNL     1      -3.622   0.854   0.427  1.00  0.00           C  
HETATM   15  C10 UNL     1      -2.329   1.279   0.221  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.338   2.240  -0.440  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.910  -0.587  -1.880  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.432  -1.581  -0.508  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.820   0.250  -1.850  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.037   1.298  -1.259  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.069   2.007   0.420  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.672  -1.611   0.401  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.036  -2.403   0.793  1.00  0.00           H  
HETATM   24  H9  UNL     1      -5.684  -1.339   0.095  1.00  0.00           H  
HETATM   25  H10 UNL     1      -4.471   1.568   0.439  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.175   2.340   0.074  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   16
CONECT    4    5   17   18
CONECT    5    6   19
CONECT    6    7    7    8
CONECT    8    9   20   21
CONECT    9   10   10   15
CONECT   10   11   22
CONECT   11   12   12   23
CONECT   12   13   14
CONECT   13   24
CONECT   14   15   15   25
CONECT   15   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
p-Hydroxyphenylacetylglycine	ChEBI
4-Hydroxyphenylacetylglycine	Kegg
N-[(4-Hydroxyphenyl)acetyl]-glycine	HMDB
N-[(p-Hydroxyphenyl)acetyl]-glycine	HMDB
[[(4-Hydroxyphenyl)acetyl]amino]acetate	HMDB
[[(4-Hydroxyphenyl)acetyl]amino]acetic acid	HMDB

Chemical Formula

C₁₀H₁₁NO₄

Average Molecular Weight

209.1986

Monoisotopic Molecular Weight

209.068807845

IUPAC Name

2-[2-(4-hydroxyphenyl)acetamido]acetic acid

Traditional Name

p-hydroxyphenylacetylglycine

CAS Registry Number

28116-23-6

SMILES

OC(=O)CNC(=O)CC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C10H11NO4/c12-8-3-1-7(2-4-8)5-9(13)11-6-10(14)15/h1-4,12H,5-6H2,(H,11,13)(H,14,15)

InChI Key

CPPDWYIPKSSNNM-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:28595 )
monocarboxylic acid amide (CHEBI:28595 )
N-acylglycine (CHEBI:28595 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 21543078)

Source

Endogenous

Endogenous (HMDB: HMDB0000735)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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
Water Solubility	2 g/L	ALOGPS
logP	0.46	ALOGPS
logP	0.2	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.54	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.15 m³·mol⁻¹	ChemAxon
Polarizability	20.13 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 Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	148.437	31661259
DarkChem	[M-H]-	143.649	31661259
AllCCS	[M+H]+	145.124	32859911
AllCCS	[M-H]-	146.385	32859911
DeepCCS	[M+H]+	143.23	30932474
DeepCCS	[M-H]-	140.835	30932474
DeepCCS	[M-2H]-	174.957	30932474
DeepCCS	[M+Na]+	149.446	30932474
AllCCS	[M+H]+	145.1	32859911
AllCCS	[M+H-H2O]+	141.2	32859911
AllCCS	[M+NH4]+	148.7	32859911
AllCCS	[M+Na]+	149.8	32859911
AllCCS	[M-H]-	146.4	32859911
AllCCS	[M+Na-2H]-	146.9	32859911
AllCCS	[M+HCOO]-	147.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.88 minutes	32390414
Predicted by Siyang on May 30, 2022	9.323 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.01 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	107.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1008.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	258.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	98.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	70.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	283.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	292.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	425.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	654.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	277.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	921.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	206.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	214.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	456.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	283.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	168.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxyphenylacetylglycine	OC(=O)CNC(=O)CC1=CC=C(O)C=C1	3576.5	Standard polar	33892256
Hydroxyphenylacetylglycine	OC(=O)CNC(=O)CC1=CC=C(O)C=C1	1922.9	Standard non polar	33892256
Hydroxyphenylacetylglycine	OC(=O)CNC(=O)CC1=CC=C(O)C=C1	2246.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxyphenylacetylglycine,1TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)CC1=CC=C(O)C=C1	2194.0	Semi standard non polar	33892256
Hydroxyphenylacetylglycine,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CC(=O)NCC(=O)O)C=C1	2175.4	Semi standard non polar	33892256
Hydroxyphenylacetylglycine,1TMS,isomer #3	C[Si](C)(C)N(CC(=O)O)C(=O)CC1=CC=C(O)C=C1	2178.4	Semi standard non polar	33892256
Hydroxyphenylacetylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)CC1=CC=C(O[Si](C)(C)C)C=C1	2220.9	Semi standard non polar	33892256
Hydroxyphenylacetylglycine,2TMS,isomer #2	C[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O)C=C1)[Si](C)(C)C	2188.4	Semi standard non polar	33892256
Hydroxyphenylacetylglycine,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(CC(=O)N(CC(=O)O)[Si](C)(C)C)C=C1	2177.4	Semi standard non polar	33892256
Hydroxyphenylacetylglycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2174.0	Semi standard non polar	33892256
Hydroxyphenylacetylglycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2163.0	Standard non polar	33892256
Hydroxyphenylacetylglycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2333.1	Standard polar	33892256
Hydroxyphenylacetylglycine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)CC1=CC=C(O)C=C1	2435.1	Semi standard non polar	33892256
Hydroxyphenylacetylglycine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(=O)NCC(=O)O)C=C1	2440.3	Semi standard non polar	33892256
Hydroxyphenylacetylglycine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)CC1=CC=C(O)C=C1	2426.1	Semi standard non polar	33892256
Hydroxyphenylacetylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2732.4	Semi standard non polar	33892256
Hydroxyphenylacetylglycine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	2674.2	Semi standard non polar	33892256
Hydroxyphenylacetylglycine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)C=C1	2716.5	Semi standard non polar	33892256
Hydroxyphenylacetylglycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2892.1	Semi standard non polar	33892256
Hydroxyphenylacetylglycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2793.4	Standard non polar	33892256
Hydroxyphenylacetylglycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2669.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-2900000000-1415e9dae0fe852be5b2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (2 TMS) - 70eV, Positive	splash10-052r-4960000000-c259468bc9a07e18a106	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyphenylacetylglycine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxyphenylacetylglycine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-056r-9610000000-cad7edd3bdf64818adae	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxyphenylacetylglycine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4i-1900000000-fcf6e7a0752287623324	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxyphenylacetylglycine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0a6r-7900000000-7353e482e3f45a50129a	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 10V, Positive-QTOF	splash10-03di-4970000000-eb650d805c8ca10605b9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 20V, Positive-QTOF	splash10-0a6r-9800000000-4e655164c76ffc2f0f8d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 40V, Positive-QTOF	splash10-056r-9400000000-f80f879428cd5b8e5a54	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 10V, Negative-QTOF	splash10-0a4i-0490000000-adf532f32e7ca51dac4a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 20V, Negative-QTOF	splash10-0a4i-5950000000-715ae07076da0da3ca9b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 40V, Negative-QTOF	splash10-0ab9-9300000000-a87e01aa42a8a324261c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 10V, Negative-QTOF	splash10-0a4i-2290000000-8d71de795ba88cb985c1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 20V, Negative-QTOF	splash10-0a4i-2900000000-d1aba2e1917f49fbb5df	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 40V, Negative-QTOF	splash10-0a4l-9700000000-ceab54edfc0fa99b5161	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 10V, Positive-QTOF	splash10-052r-1910000000-1bd1fc053034b378cb72	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 20V, Positive-QTOF	splash10-0a4i-9700000000-85acdf94596569b8e7c4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyphenylacetylglycine 40V, Positive-QTOF	splash10-0a6r-9700000000-31e7a20a6025dcbd29d7	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 500 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX 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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Not Available	Not Available	Normal	21543078	details
Urine	Detected and Quantified	<0.0025–0.0079 umol/mmol creatinine	Adult (25-30 years old)	Both	Not Available	23062437	details
Urine	Detected and Quantified	<0.0025–0.0097 umol/mmol creatinine	Adult (25-30 years old)	Both	Not Available	23062437	details
Urine	Detected and Quantified	<0.0025–0.0048 umol/mmol creatinine	Adult (25-30 years old)	Both	Not Available	23062437	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

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

FDB022212

KNApSAcK ID

Not Available

Chemspider ID

389604

KEGG Compound ID

C05596

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440732

PDB ID

Not Available

ChEBI ID

28595

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

Ramsdell HS, Baretz BH, Tanaka K: Mass spectrometric studies of twenty-one metabolically important acylglycines. Biomed Mass Spectrom. 1977 Aug;4(4):220-5. [PubMed:912020 ]
Tanaka K, Hine DG: Compilation of gas chromatographic retention indices of 163 metabolically important organic acids, and their use in detection of patients with organic acidurias. J Chromatogr. 1982 Apr 30;239:301-22. [PubMed:7096501 ]
Tanaka K, West-Dull A, Hine DG, Lynn TB, Lowe T: Gas-chromatographic method of analysis for urinary organic acids. II. Description of the procedure, and its application to diagnosis of patients with organic acidurias. Clin Chem. 1980 Dec;26(13):1847-53. [PubMed:7438430 ]
NAKAJIMA T, SANO I: NEW METABOLITES OF P-TYRAMINE FROM THE URINE OF RATS. Biochim Biophys Acta. 1964 Jul 15;90:37-44. [PubMed:14201174 ]
Goodwin BL, Ruthven CR, King GS, Sandler M: Metabolism of 3, 4-dihydroxyphenylalanine, its metabolites and analogues in vivo in the rat: urinary excretion pattern. Xenobiotica. 1978 Oct;8(10):629-51. [PubMed:716472 ]
Tanaka K, Hine DG, West-Dull A, Lynn TB: Gas-chromatographic method of analysis for urinary organic acids. I. Retention indices of 155 metabolically important compounds. Clin Chem. 1980 Dec;26(13):1839-46. [PubMed:7438429 ]

Enzymes

Enzyme Details

1. Glycine N-acyltransferase

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:: GLYAT
Uniprot ID:: Q6IB77
Molecular weight:: 18506.33

Enzyme Details

2. Glycine N-acyltransferase-like protein 1

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:: GLYATL1
Uniprot ID:: Q969I3
Molecular weight:: 35100.895

Enzyme Details

3. Glycine N-acyltransferase-like protein 2

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:: GLYATL2
Uniprot ID:: Q8WU03
Molecular weight:: 34277.055

Enzyme Details

4. Glycine N-acyltransferase-like protein 3

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:: GLYATL3
Uniprot ID:: Q5SZD4
Molecular weight:: 32703.3

Enzyme Details

5. N-acetyltransferase ESCO1

General function:: Involved in damaged DNA binding
Specific function:: Acetyltransferase required for the establishment of sister chromatid cohesion and couple the processes of cohesion and DNA replication to ensure that only sister chromatids become paired together. In contrast to the structural cohesins, the deposition and establishment factors are required only during S phase. Acts by mediating the acetylation of cohesin component SMC3
Gene Name:: ESCO1
Uniprot ID:: Q5FWF5
Molecular weight:: 94982.2

Showing metabocard for Hydroxyphenylacetylglycine (HMDB0000735)

MOL for HMDB0000735 (Hydroxyphenylacetylglycine)

3D MOL for HMDB0000735 (Hydroxyphenylacetylglycine)

3D SDF for HMDB0000735 (Hydroxyphenylacetylglycine)

3D-SDF for HMDB0000735 (Hydroxyphenylacetylglycine)

PDB for HMDB0000735 (Hydroxyphenylacetylglycine)

3D PDB for HMDB0000735 (Hydroxyphenylacetylglycine)

SMILES for HMDB0000735 (Hydroxyphenylacetylglycine)

INCHI for HMDB0000735 (Hydroxyphenylacetylglycine)

Structure for HMDB0000735 (Hydroxyphenylacetylglycine)

3D Structure for HMDB0000735 (Hydroxyphenylacetylglycine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes