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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:49:33 UTC

Update Date

2023-02-21 17:22:01 UTC

HMDB ID

HMDB0032388

Secondary Accession Numbers

HMDB32388

Metabolite Identification

Common Name

Methyl n-acetylanthranilate

Description

Methyl n-acetylanthranilate, also known as 2-(acetylamino)-benzoic acid or methyl 2-(acetylamino)benzoate, belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated. Based on a literature review very few articles have been published on Methyl n-acetylanthranilate.

Structure

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

  Mrv0541 02241221512D          

 14 14  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1994    1.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032388

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C1=CC=CC=C1NC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO3/c1-7(12)11-9-6-4-3-5-8(9)10(13)14-2/h3-6H,1-2H3,(H,11,12)

> <INCHI_KEY>
UYQKZKVNYKOXHG-UHFFFAOYSA-N

> <FORMULA>
C10H11NO3

> <MOLECULAR_WEIGHT>
193.1992

> <EXACT_MASS>
193.073893223

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.738844741618266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-acetamidobenzoate

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
1.864433147333333

> <ALOGPS_LOGS>
-2.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.54706495650612

> <JCHEM_PKA_STRONGEST_BASIC>
-4.485467380436943

> <JCHEM_POLAR_SURFACE_AREA>
55.400000000000006

> <JCHEM_REFRACTIVITY>
52.9463

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-acetamidobenzoate

> <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  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.239   3.556   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14    2                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl N-acetylanthranilic acid	Generator
2-(Acetylamino)-benzoic acid	HMDB
2-Acetylaminobenzoic acid, methyl ester	HMDB
Anthranilic acid, N-acetyl-, methyl ester	HMDB
Anthranilic acid, N-acetyl-, methyl ester (8ci)	HMDB
Benzoic acid, 2-(acetylamino)-, methyl ester	HMDB
Methyl 2-(acetylamino)benzoate	HMDB
Methyl N-acetoanthranilate	HMDB
N-Acetyl methyl anthranilate	HMDB
N-Acetylanthranilate	HMDB
N-Acetylanthranilic acid	HMDB
N-[2-(Methoxycarbonyl)phenyl]ethanimidate	HMDB

Chemical Formula

C₁₀H₁₁NO₃

Average Molecular Weight

193.1992

Monoisotopic Molecular Weight

193.073893223

IUPAC Name

methyl 2-acetamidobenzoate

Traditional Name

methyl 2-acetamidobenzoate

CAS Registry Number

2719-08-6

SMILES

COC(=O)C1=CC=CC=C1NC(C)=O

InChI Identifier

InChI=1S/C10H11NO3/c1-7(12)11-9-6-4-3-5-8(9)10(13)14-2/h3-6H,1-2H3,(H,11,12)

InChI Key

UYQKZKVNYKOXHG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Acylaminobenzoic acid and derivatives

Alternative Parents

Substituents

Acylaminobenzoic acid or derivatives
Acetanilide
Benzoate ester
N-acetylarylamine
Anilide
Benzoyl
N-arylamide
Acetamide
Vinylogous amide
Methyl ester
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0032388)
Cytoplasm (HMDB: HMDB0032388)

Source

Endogenous

Endogenous (HMDB: HMDB0032388)

Exogenous

Food

Food (HMDB: HMDB0032388)

Exogenous (HMDB: HMDB0032388)

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	1.65	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.99 g/L	ALOGPS
logP	1.46	ALOGPS
logP	1.86	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	12.55	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	52.95 m³·mol⁻¹	ChemAxon
Polarizability	19.74 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]+	144.756	31661259
DarkChem	[M-H]-	141.417	31661259
DeepCCS	[M+H]+	143.153	30932474
DeepCCS	[M-H]-	140.605	30932474
DeepCCS	[M-2H]-	176.138	30932474
DeepCCS	[M+Na]+	151.675	30932474
AllCCS	[M+H]+	142.2	32859911
AllCCS	[M+H-H2O]+	138.1	32859911
AllCCS	[M+NH4]+	146.1	32859911
AllCCS	[M+Na]+	147.2	32859911
AllCCS	[M-H]-	141.9	32859911
AllCCS	[M+Na-2H]-	142.6	32859911
AllCCS	[M+HCOO]-	143.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl n-acetylanthranilate	COC(=O)C1=CC=CC=C1NC(C)=O	2381.8	Standard polar	33892256
Methyl n-acetylanthranilate	COC(=O)C1=CC=CC=C1NC(C)=O	1716.9	Standard non polar	33892256
Methyl n-acetylanthranilate	COC(=O)C1=CC=CC=C1NC(C)=O	1628.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl n-acetylanthranilate,1TMS,isomer #1	COC(=O)C1=CC=CC=C1N(C(C)=O)[Si](C)(C)C	1589.4	Semi standard non polar	33892256
Methyl n-acetylanthranilate,1TMS,isomer #1	COC(=O)C1=CC=CC=C1N(C(C)=O)[Si](C)(C)C	1698.5	Standard non polar	33892256
Methyl n-acetylanthranilate,1TBDMS,isomer #1	COC(=O)C1=CC=CC=C1N(C(C)=O)[Si](C)(C)C(C)(C)C	1817.4	Semi standard non polar	33892256
Methyl n-acetylanthranilate,1TBDMS,isomer #1	COC(=O)C1=CC=CC=C1N(C(C)=O)[Si](C)(C)C(C)(C)C	1906.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl n-acetylanthranilate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0h4o-3900000000-09aca43ca7b5c7498a3d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl n-acetylanthranilate 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl n-acetylanthranilate 10V, Positive-QTOF	splash10-0f6x-0900000000-eaba09e4747037493071	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl n-acetylanthranilate 20V, Positive-QTOF	splash10-0udi-0900000000-40469fdcb699f98f8852	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl n-acetylanthranilate 40V, Positive-QTOF	splash10-0v4l-5900000000-db1d6b704d93ee53a7da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl n-acetylanthranilate 10V, Negative-QTOF	splash10-0006-0900000000-5cf8c42a1b494186c472	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl n-acetylanthranilate 20V, Negative-QTOF	splash10-0f6x-1900000000-2015760075b0b9e10b4d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl n-acetylanthranilate 40V, Negative-QTOF	splash10-0006-5900000000-94832726fcf935953d5e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl n-acetylanthranilate 10V, Negative-QTOF	splash10-00kf-0900000000-67f5fba599ea1a0c3abd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl n-acetylanthranilate 20V, Negative-QTOF	splash10-001i-3900000000-c46cc8ef09860e69aaa4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl n-acetylanthranilate 40V, Negative-QTOF	splash10-00kf-9500000000-24e3fde64de6865b6906	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl n-acetylanthranilate 10V, Positive-QTOF	splash10-0h93-0900000000-21e3e7f12cb00ab0491f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl n-acetylanthranilate 20V, Positive-QTOF	splash10-00di-0900000000-f34df9b62ded49695d45	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl n-acetylanthranilate 40V, Positive-QTOF	splash10-00xu-7900000000-bd6d6709de93fba62d53	2021-09-23	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB009808

KNApSAcK ID

Not Available

Chemspider ID

16658

KEGG Compound ID

C06332

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17623

PDB ID

Not Available

ChEBI ID

16803

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

(). EAFUS: Everything Added to Food in the United States.. .

Showing metabocard for Methyl n-acetylanthranilate (HMDB0032388)

MOL for HMDB0032388 (Methyl n-acetylanthranilate)

3D MOL for HMDB0032388 (Methyl n-acetylanthranilate)

3D SDF for HMDB0032388 (Methyl n-acetylanthranilate)

3D-SDF for HMDB0032388 (Methyl n-acetylanthranilate)

PDB for HMDB0032388 (Methyl n-acetylanthranilate)

3D PDB for HMDB0032388 (Methyl n-acetylanthranilate)

SMILES for HMDB0032388 (Methyl n-acetylanthranilate)

INCHI for HMDB0032388 (Methyl n-acetylanthranilate)

Structure for HMDB0032388 (Methyl n-acetylanthranilate)

3D Structure for HMDB0032388 (Methyl n-acetylanthranilate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra