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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-22 16:40:57 UTC

Update Date

2021-09-22 16:40:57 UTC

HMDB ID

HMDB0301727

Secondary Accession Numbers

None

Metabolite Identification

Common Name

p-Coumaroyl glycolic acid

Description

P-coumaroyl glycolic acid is a member of the class of compounds known as coumaric acid esters. Coumaric acid esters are aromatic compounds containing an ester derivative of coumaric acid. P-coumaroyl glycolic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). P-coumaroyl glycolic acid can be found in lentils, which makes P-coumaroyl glycolic acid a potential biomarker for the consumption of this food product.

Structure

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


  Mrv0541 02241223302D          

 16 16  0  0  0  0            999 V2000
   -2.7107   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4252   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4252   -1.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7107   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9962   -1.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9962   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1397   -2.1509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5673   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8616   -0.9134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472    0.3241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5761   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2906   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0051   -0.5009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2906   -1.7384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301727

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)COC(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O5/c12-9-4-1-8(2-5-9)3-6-11(15)16-7-10(13)14/h1-6,12H,7H2,(H,13,14)/b6-3+

> <INCHI_KEY>
RMPWEBYRPJQKNT-ZZXKWVIFSA-N

> <FORMULA>
C11H10O5

> <MOLECULAR_WEIGHT>
222.1941

> <EXACT_MASS>
222.05282343

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
21.57762879453054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}acetic acid

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
1.689731636

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.398711149616759

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5191941612554634

> <JCHEM_PKA_STRONGEST_BASIC>
-5.954732444560503

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
55.89450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.060  -0.935   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.394  -1.705   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.394  -3.245   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.060  -4.015   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.726  -3.245   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.726  -1.705   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.727  -4.015   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.393  -0.935   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.059  -1.705   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.275  -0.935   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.608  -1.705   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.275   0.605   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.942  -0.935   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.276  -1.705   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.610  -0.935   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.276  -3.245   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    8                                                  
CONECT    7    3                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0301727
HETATM    1  O1  UNL     1       3.921   0.770   1.637  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.727   0.252   0.848  1.00  0.00           C  
HETATM    3  O2  UNL     1       6.042   0.682   0.877  1.00  0.00           O  
HETATM    4  C2  UNL     1       4.384  -0.808  -0.138  1.00  0.00           C  
HETATM    5  O3  UNL     1       2.994  -1.143  -0.046  1.00  0.00           O  
HETATM    6  C3  UNL     1       2.058  -0.149  -0.275  1.00  0.00           C  
HETATM    7  O4  UNL     1       2.470   1.005  -0.554  1.00  0.00           O  
HETATM    8  C4  UNL     1       0.618  -0.445  -0.192  1.00  0.00           C  
HETATM    9  C5  UNL     1      -0.295   0.470  -0.403  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.732   0.255  -0.340  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.571   1.321  -0.587  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.946   1.218  -0.551  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.509  -0.004  -0.254  1.00  0.00           C  
HETATM   14  O5  UNL     1      -5.912  -0.105  -0.218  1.00  0.00           O  
HETATM   15  C10 UNL     1      -3.686  -1.065  -0.008  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.308  -0.959  -0.045  1.00  0.00           C  
HETATM   17  H1  UNL     1       6.644   0.649   0.050  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.622  -0.417  -1.143  1.00  0.00           H  
HETATM   19  H3  UNL     1       5.014  -1.687   0.073  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.311  -1.445   0.049  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.091   1.464  -0.644  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.135   2.298  -0.824  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.599   2.068  -0.748  1.00  0.00           H  
HETATM   24  H8  UNL     1      -6.404  -0.350  -1.083  1.00  0.00           H  
HETATM   25  H9  UNL     1      -4.131  -2.044   0.230  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.668  -1.832   0.158  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5   18   19
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9    9   20
CONECT    9   10   21
CONECT   10   11   11   16
CONECT   11   12   22
CONECT   12   13   13   23
CONECT   13   14   15
CONECT   14   24
CONECT   15   16   16   25
CONECT   16   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}acetate	Generator
p-Coumaroyl glycolate	Generator

Chemical Formula

C₁₁H₁₀O₅

Average Molecular Weight

222.1941

Monoisotopic Molecular Weight

222.05282343

IUPAC Name

2-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}acetic acid

Traditional Name

{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}acetic acid

CAS Registry Number

Not Available

SMILES

OC(=O)COC(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C11H10O5/c12-9-4-1-8(2-5-9)3-6-11(15)16-7-10(13)14/h1-6,12H,7H2,(H,13,14)/b6-3+

InChI Key

RMPWEBYRPJQKNT-ZZXKWVIFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0301727)

Food

Pulse

Lentil

Lentils (FooDB: FOOD00098)

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	2.43	ALOGPS
logP	1.69	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.52	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	55.89 m³·mol⁻¹	ChemAxon
Polarizability	21.58 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
AllCCS	[M+H]+	147.385	32859911
AllCCS	[M+H-H2O]+	143.526	32859911
AllCCS	[M+Na]+	152.005	32859911
AllCCS	[M+NH4]+	150.972	32859911
AllCCS	[M-H]-	148.706	32859911
AllCCS	[M+Na-2H]-	148.957	32859911
AllCCS	[M+HCOO]-	149.332	32859911
DeepCCS	[M+H]+	148.929	30932474
DeepCCS	[M-H]-	146.533	30932474
DeepCCS	[M-2H]-	179.534	30932474
DeepCCS	[M+Na]+	154.945	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.6763 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.29 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1592.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	296.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	116.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	108.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	418.3 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	425.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	107.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	863.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	356.0 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	1136.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	254.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	302.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	449.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	168.6 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	98.0 seconds	40023050

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 - p-Coumaroyl glycolic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2900000000-191ef144359006a6a923	2017-07-27	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 - p-Coumaroyl glycolic acid 10V, Positive-QTOF	splash10-00di-1490000000-9551d513ba17c6ef40ad	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Coumaroyl glycolic acid 20V, Positive-QTOF	splash10-0002-2930000000-73930f42508179ef582a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Coumaroyl glycolic acid 40V, Positive-QTOF	splash10-014j-6900000000-007ced050f9712ae375b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Coumaroyl glycolic acid 10V, Negative-QTOF	splash10-00dj-1790000000-17b865e5d38deeeb8fd0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Coumaroyl glycolic acid 20V, Negative-QTOF	splash10-0092-3930000000-01d5573e8b72d1106bd4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Coumaroyl glycolic acid 40V, Negative-QTOF	splash10-0002-5900000000-85535946cd8c757d9fbd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Coumaroyl glycolic acid 10V, Positive-QTOF	splash10-0002-0910000000-ffc9eb8d4003932f7286	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Coumaroyl glycolic acid 20V, Positive-QTOF	splash10-00kb-1900000000-735447454fb30a73b770	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Coumaroyl glycolic acid 40V, Positive-QTOF	splash10-016u-9600000000-df181b6b69a60a0eb91e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Coumaroyl glycolic acid 10V, Negative-QTOF	splash10-014i-0910000000-e0f88b2ea8751ecc424a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Coumaroyl glycolic acid 20V, Negative-QTOF	splash10-014i-1900000000-bdb5244c03c04b215d71	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Coumaroyl glycolic acid 40V, Negative-QTOF	splash10-014i-2900000000-8624cd560522f0cebc8b	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB000290

KNApSAcK ID

Not Available

Chemspider ID

59696647

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101219702

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for p-Coumaroyl glycolic acid (HMDB0301727)

MOL for HMDB0301727 (p-Coumaroyl glycolic acid)

3D MOL for HMDB0301727 (p-Coumaroyl glycolic acid)

3D SDF for HMDB0301727 (p-Coumaroyl glycolic acid)

3D-SDF for HMDB0301727 (p-Coumaroyl glycolic acid)

PDB for HMDB0301727 (p-Coumaroyl glycolic acid)

3D PDB for HMDB0301727 (p-Coumaroyl glycolic acid)

SMILES for HMDB0301727 (p-Coumaroyl glycolic acid)

INCHI for HMDB0301727 (p-Coumaroyl glycolic acid)

Structure for HMDB0301727 (p-Coumaroyl glycolic acid)

3D Structure for HMDB0301727 (p-Coumaroyl glycolic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra