NP-MRD: Showing NP-Card for m-Chlorohippuric acid (NP0086751)

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Record Information

Version

1.0

Created at

2022-05-11 16:29:58 UTC

Updated at

2022-05-11 16:29:59 UTC

NP-MRD ID

NP0086751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

m-Chlorohippuric acid

Description

M-Chlorohippuric acid, also known as m-chlorohippate, 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 1987 (PMID: 3107223). M-Chlorohippuric acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231219032D          

 14 14  0  0  0  0            999 V2000
   11.5208   -9.8298    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.2353   -6.9423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3787   -4.8797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0932   -6.1173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6643   -6.9423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9498   -8.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9498   -7.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6643   -6.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2353   -8.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6643   -8.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2353   -9.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6643   -9.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9498   -9.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3787   -5.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2  7  2  0  0  0  0
  3 14  1  0  0  0  0
  4 14  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  2  0  0  0  0
  6 10  1  0  0  0  0
  8 14  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CNC(=O)C1=CC(Cl)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H8ClNO3/c10-7-3-1-2-6(4-7)9(14)11-5-8(12)13/h1-4H,5H2,(H,11,14)(H,12,13)

> <INCHI_KEY>
ICYUIIJXZHPESK-UHFFFAOYSA-N

> <FORMULA>
C9H8ClNO3

> <MOLECULAR_WEIGHT>
213.618

> <EXACT_MASS>
213.019270834

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.82134397998636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.97

> <JCHEM_LOGP>
1.1295901606666665

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.650377870743824

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1859395423462797

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5955546273853058

> <JCHEM_POLAR_SURFACE_AREA>
66.39999999999999

> <JCHEM_REFRACTIVITY>
50.92250000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
m-chlorohippuric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      21.505 -18.349   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0      22.839 -12.959   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      26.840  -9.109   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      28.174 -11.419   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      25.507 -12.959   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      24.173 -15.269   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.173 -13.729   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.507 -11.419   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.839 -16.039   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.507 -16.039   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.839 -17.579   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.507 -17.579   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.173 -18.349   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.840 -10.649   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2    7                                                            
CONECT    3   14                                                            
CONECT    4   14                                                            
CONECT    5    7    8                                                       
CONECT    6    7    9   10                                                  
CONECT    7    2    5    6                                                  
CONECT    8    5   14                                                       
CONECT    9    6   11                                                       
CONECT   10    6   12                                                       
CONECT   11    1    9   13                                                  
CONECT   12   10   13                                                       
CONECT   13   11   12                                                       
CONECT   14    3    4    8                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
m-Chlorohippate	Generator
m-Chlorohippic acid	Generator
3-Chlorohippuric acid	HMDB
3-Chlorohippate	HMDB
3-Chlorohippic acid	HMDB
(3-Chloro-benzoylamino)-acetic acid	HMDB
(3-Chlorobenzoylamino)acetic acid	HMDB
m-Chlorohippurate	HMDB
N-(3-Chlorobenzoyl)glycine	HMDB
2-{[(3-chlorophenyl)(hydroxy)methylidene]amino}acetate	HMDB

Chemical Formula

C₉H₈ClNO₃

Average Mass

213.6180 Da

Monoisotopic Mass

213.01927 Da

IUPAC Name

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

Traditional Name

m-chlorohippuric acid

CAS Registry Number

Not Available

SMILES

OC(=O)CNC(=O)C1=CC(Cl)=CC=C1

InChI Identifier

InChI=1S/C9H8ClNO3/c10-7-3-1-2-6(4-7)9(14)11-5-8(12)13/h1-4H,5H2,(H,11,14)(H,12,13)

InChI Key

ICYUIIJXZHPESK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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
Halobenzoic acid or derivatives
3-halobenzoic acid or derivatives
Benzoyl
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	0.97	ALOGPS
logP	1.13	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.19	ChemAxon
pKa (Strongest Basic)	-1.6	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	50.92 m³·mol⁻¹	ChemAxon
Polarizability	19.82 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

HMDB0001309

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022545

KNApSAcK ID

Not Available

Chemspider ID

435

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6149

PubChem Compound

448

PDB ID

Not Available

ChEBI ID

613377

Good Scents ID

Not Available

References

General References

Welch RM, Lai AA, Schroeder DH: Pharmacological significance of the species differences in bupropion metabolism. Xenobiotica. 1987 Mar;17(3):287-98. [PubMed:3107223 ]

Showing NP-Card for m-Chlorohippuric acid (NP0086751)

MOL for NP0086751 (m-Chlorohippuric acid)

3D MOL for NP0086751 (m-Chlorohippuric acid)

3D SDF for NP0086751 (m-Chlorohippuric acid)

3D-SDF for NP0086751 (m-Chlorohippuric acid)

PDB for NP0086751 (m-Chlorohippuric acid)

3D PDB for NP0086751 (m-Chlorohippuric acid)

SMILES for NP0086751 (m-Chlorohippuric acid)

INCHI for NP0086751 (m-Chlorohippuric acid)

Structure for NP0086751 (m-Chlorohippuric acid)

3D Structure for NP0086751 (m-Chlorohippuric acid)