NP-MRD: Showing NP-Card for p-Methylhippuric acid (NP0333429)

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Record Information

Version

1.0

Created at

2024-06-18 20:45:10 UTC

Updated at

2024-09-03 04:22:26 UTC

NP-MRD ID

NP0333429

DOI

https://doi.org/10.57994/2862

Secondary Accession Numbers

None

Natural Product Identification

Common Name

p-Methylhippuric acid

Description

P-Methylhippuric acid, also known as 4-methylhippate or N-(p-toluoyl)-glycine, belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine. It was first documented in 1976 (PMID: 1008992). P-Methylhippuric acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 22770225).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016522D          

 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
    8.7891  -11.4506    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  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333429

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
NRSCPTLHWVWLLH-UHFFFAOYSA-N

> <FORMULA>
C10H11NO3

> <MOLECULAR_WEIGHT>
193.1992

> <EXACT_MASS>
193.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.774244794215974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(4-methylphenyl)formamido]acetic acid

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
1.0389668736666666

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.322160083517577

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.742765368137697

> <JCHEM_PKA_STRONGEST_BASIC>
-1.223438075015142

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
51.1589

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4-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      16.406 -21.374   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                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   14                                                  
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    6                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
4-Methylhippuric acid	ChEBI
4-Methylhippate	Generator
4-Methylhippic acid	Generator
p-Methylhippate	Generator
p-Methylhippic acid	Generator
((4-Methylbenzoyl)amino)acetic acid	HMDB
(4-Methyl-benzoylamino)-acetic acid	HMDB
N-(4-Methylbenzoyl)glycine	HMDB
N-(p-Toluoyl)-glycine	HMDB
N-(p-Toluoyl)glycine	HMDB
p-Toluric acid	HMDB
Para-methylhippuric acid	HMDB

Chemical Formula

C₁₀H₁₁NO₃

Average Mass

193.1992 Da

Monoisotopic Mass

193.07389 Da

IUPAC Name

2-[(4-methylphenyl)formamido]acetic acid

Traditional Name

[(4-methylphenyl)formamido]acetic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

NRSCPTLHWVWLLH-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-18	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-18	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-18	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-18	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hippuric acids

Alternative Parents

Substituents

Hippuric acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
P-toluamide
Toluamide
Benzoyl
Toluene
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acylglycine (CHEBI:68552 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	0.7	ALOGPS
logP	1.04	ChemAxon
logS	-2.6	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	19.77 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

External Links

HMDB ID

HMDB0013292

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029366

KNApSAcK ID

Not Available

Chemspider ID

87986

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methylhippuric acid

METLIN ID

Not Available

PubChem Compound

97479

PDB ID

Not Available

ChEBI ID

68552

Good Scents ID

Not Available

References

General References

Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
Proctor JW: Rat sarcoma model supports both "soil seed" and "mechanical" theories of metastatic spread. Br J Cancer. 1976 Dec;34(6):651-4. doi: 10.1038/bjc.1976.227. [PubMed:1008992 ]

Showing NP-Card for p-Methylhippuric acid (NP0333429)

MOL for NP0333429 (p-Methylhippuric acid)

3D MOL for NP0333429 (p-Methylhippuric acid)

3D SDF for NP0333429 (p-Methylhippuric acid)

3D-SDF for NP0333429 (p-Methylhippuric acid)

PDB for NP0333429 (p-Methylhippuric acid)

3D PDB for NP0333429 (p-Methylhippuric acid)

SMILES for NP0333429 (p-Methylhippuric acid)

INCHI for NP0333429 (p-Methylhippuric acid)

Structure for NP0333429 (p-Methylhippuric acid)

3D Structure for NP0333429 (p-Methylhippuric acid)