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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2009-11-30 15:51:37 UTC

Update Date

2023-02-21 17:17:57 UTC

HMDB ID

HMDB0013245

Secondary Accession Numbers

HMDB13245

Metabolite Identification

Common Name

m-Methylhippuric acid

Description

m-Methylhippuric acid, also known as 3-methylhippate, 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. m-Methylhippuric acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on m-Methylhippuric acid.

Structure

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


  Mrv1652303102016512D          

 14 14  0  0  0  0            999 V2000
   10.9326  -10.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9326  -11.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2180   -9.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2180  -11.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5036  -10.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5036  -11.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6470   -9.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3615  -10.2131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0760   -9.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7905  -10.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5049   -9.8006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7905  -11.0381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6470   -8.9756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2180  -12.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 10  2  0  0  0  0
 13  7  2  0  0  0  0
 14  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013245

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=CC=C1)C(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO3/c1-7-3-2-4-8(5-7)10(14)11-6-9(12)13/h2-5H,6H2,1H3,(H,11,14)(H,12,13)

> <INCHI_KEY>
YKAKNMHEIJUKEX-UHFFFAOYSA-N

> <FORMULA>
C10H11NO3

> <MOLECULAR_WEIGHT>
193.1992

> <EXACT_MASS>
193.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.647314610299844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3-methylphenyl)formamido]acetic acid

> <ALOGPS_LOGP>
0.69

> <JCHEM_LOGP>
1.0389668736666666

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.163154109776176

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.743625366695486

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2175297873718898

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
51.1589

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3-methylphenyl)formamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      20.408 -19.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.408 -20.604   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.074 -18.294   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.074 -21.374   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.740 -19.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.740 -20.604   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.741 -18.294   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      23.075 -19.064   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      24.409 -18.294   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.742 -19.064   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      27.076 -18.294   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      25.742 -20.604   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      21.741 -16.754   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      19.074 -22.914   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6   14                                                  
CONECT    5    3    6                                                       
CONECT    6    4    5                                                       
CONECT    7    1    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7                                                            
CONECT   14    4                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Methylhippuric acid	ChEBI
3-Methylhippate	Generator
3-Methylhippic acid	Generator
m-Methylhippate	Generator
m-Methylhippic acid	Generator
Meta-methylhippuric acid	MeSH

Chemical Formula

C₁₀H₁₁NO₃

Average Molecular Weight

193.1992

Monoisotopic Molecular Weight

193.073893223

IUPAC Name

2-[(3-methylphenyl)formamido]acetic acid

Traditional Name

[(3-methylphenyl)formamido]acetic acid

CAS Registry Number

Not Available

SMILES

CC1=CC(=CC=C1)C(=O)NCC(O)=O

InChI Identifier

InChI=1S/C10H11NO3/c1-7-3-2-4-8(5-7)10(14)11-6-9(12)13/h2-5H,6H2,1H3,(H,11,14)(H,12,13)

InChI Key

YKAKNMHEIJUKEX-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
Toluene
Monocyclic benzene moiety
Benzenoid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organonitrogen compound
Organic oxygen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acylglycine (CHEBI:68500 )

Ontology

Not Available

Endogenous (HMDB: HMDB0013245)

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	0.56 g/L	ALOGPS
logP	0.69	ALOGPS
logP	1.04	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.74	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.16 m³·mol⁻¹	ChemAxon
Polarizability	19.65 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]+	143.668	31661259
DarkChem	[M-H]-	139.259	31661259
DeepCCS	[M+H]+	141.61	30932474
DeepCCS	[M-H]-	138.277	30932474
DeepCCS	[M-2H]-	175.272	30932474
DeepCCS	[M+Na]+	150.81	30932474
AllCCS	[M+H]+	141.9	32859911
AllCCS	[M+H-H2O]+	137.8	32859911
AllCCS	[M+NH4]+	145.7	32859911
AllCCS	[M+Na]+	146.8	32859911
AllCCS	[M-H]-	142.3	32859911
AllCCS	[M+Na-2H]-	143.0	32859911
AllCCS	[M+HCOO]-	143.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
m-Methylhippuric acid	CC1=CC(=CC=C1)C(=O)NCC(O)=O	2755.9	Standard polar	33892256
m-Methylhippuric acid	CC1=CC(=CC=C1)C(=O)NCC(O)=O	1746.1	Standard non polar	33892256
m-Methylhippuric acid	CC1=CC(=CC=C1)C(=O)NCC(O)=O	1912.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
m-Methylhippuric acid,1TMS,isomer #1	CC1=CC=CC(C(=O)NCC(=O)O[Si](C)(C)C)=C1	1926.1	Semi standard non polar	33892256
m-Methylhippuric acid,1TMS,isomer #2	CC1=CC=CC(C(=O)N(CC(=O)O)[Si](C)(C)C)=C1	1892.2	Semi standard non polar	33892256
m-Methylhippuric acid,2TMS,isomer #1	CC1=CC=CC(C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)=C1	1882.2	Semi standard non polar	33892256
m-Methylhippuric acid,2TMS,isomer #1	CC1=CC=CC(C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)=C1	1912.9	Standard non polar	33892256
m-Methylhippuric acid,2TMS,isomer #1	CC1=CC=CC(C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)=C1	2167.0	Standard polar	33892256
m-Methylhippuric acid,1TBDMS,isomer #1	CC1=CC=CC(C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)=C1	2172.2	Semi standard non polar	33892256
m-Methylhippuric acid,1TBDMS,isomer #2	CC1=CC=CC(C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)=C1	2135.3	Semi standard non polar	33892256
m-Methylhippuric acid,2TBDMS,isomer #1	CC1=CC=CC(C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2368.8	Semi standard non polar	33892256
m-Methylhippuric acid,2TBDMS,isomer #1	CC1=CC=CC(C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2309.2	Standard non polar	33892256
m-Methylhippuric acid,2TBDMS,isomer #1	CC1=CC=CC(C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2423.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - m-Methylhippuric acid EI-B (Non-derivatized)	splash10-014i-6900000000-4a327638e0211a45d7b3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - m-Methylhippuric acid EI-B (Non-derivatized)	splash10-014i-6900000000-4a327638e0211a45d7b3	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Methylhippuric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-7900000000-f7d1bc5778e77d194464	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Methylhippuric acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9210000000-4525c7f8a9698e49bc29	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Methylhippuric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - m-Methylhippuric acid 20V, Positive-QTOF	splash10-014i-3940000000-b0901936fc736cb40192	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - m-Methylhippuric acid 20V, Negative-QTOF	splash10-014i-3940000000-23571c04cabfb71b7e80	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - m-Methylhippuric acid 40V, Positive-QTOF	splash10-0006-9000000000-c4812f063baaaa267a6e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - m-Methylhippuric acid 10V, Positive-QTOF	splash10-014i-0900000000-0dd6000e9860793083c0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - m-Methylhippuric acid 20V, Positive-QTOF	splash10-014i-1900000000-459ec76d8483cfdecaa3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Methylhippuric acid 10V, Positive-QTOF	splash10-00kf-1900000000-06ad39599696e1f52327	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Methylhippuric acid 20V, Positive-QTOF	splash10-014i-3900000000-07f81e34909c892b5208	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Methylhippuric acid 40V, Positive-QTOF	splash10-00kf-9200000000-c7cbcfe6817228a82cc2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Methylhippuric acid 10V, Negative-QTOF	splash10-0006-0900000000-0cd9bf507120d6806583	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Methylhippuric acid 20V, Negative-QTOF	splash10-0006-2900000000-6beed75465268298f67f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Methylhippuric acid 40V, Negative-QTOF	splash10-0596-9000000000-71524cf3c73a65532556	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Methylhippuric acid 10V, Negative-QTOF	splash10-0007-5900000000-5f4c8fec6477b6f47b96	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Methylhippuric acid 20V, Negative-QTOF	splash10-0006-9000000000-83980cc786fec5759407	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Methylhippuric acid 40V, Negative-QTOF	splash10-0006-9000000000-5671d4c535a6553aaf0d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Methylhippuric acid 10V, Positive-QTOF	splash10-00kf-3900000000-60ef001134465e7b2c98	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Methylhippuric acid 20V, Positive-QTOF	splash10-0006-9300000000-faf58a76a74f72657d73	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Methylhippuric acid 40V, Positive-QTOF	splash10-0006-9000000000-5c9681b6dcf23ed12c88	2021-09-25	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

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

FDB029355

KNApSAcK ID

Not Available

Chemspider ID

89642

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methylhippuric acid

METLIN ID

Not Available

PubChem Compound

99223

PDB ID

Not Available

ChEBI ID

68500

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

Proctor JW: Rat sarcoma model supports both "soil seed" and "mechanical" theories of metastatic spread. Br J Cancer. 1976 Dec;34(6):651-4. [PubMed:1008992 ]

Showing metabocard for m-Methylhippuric acid (HMDB0013245)

MOL for HMDB0013245 (m-Methylhippuric acid)

3D MOL for HMDB0013245 (m-Methylhippuric acid)

3D SDF for HMDB0013245 (m-Methylhippuric acid)

3D-SDF for HMDB0013245 (m-Methylhippuric acid)

PDB for HMDB0013245 (m-Methylhippuric acid)

3D PDB for HMDB0013245 (m-Methylhippuric acid)

SMILES for HMDB0013245 (m-Methylhippuric acid)

INCHI for HMDB0013245 (m-Methylhippuric acid)

Structure for HMDB0013245 (m-Methylhippuric acid)

3D Structure for HMDB0013245 (m-Methylhippuric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra