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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:45:53 UTC

Update Date

2021-09-26 22:57:33 UTC

HMDB ID

HMDB0247698

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Benzoic acid, 2-(acetyloxy)-5-amino-

Description

Benzoic acid, 2-(acetyloxy)-5-amino-, also known as acetyl-5-asa or acetyl-5-aminosalicylic acid, belongs to the class of organic compounds known as acylsalicylic acids. These are o-acylated derivatives of salicylic acid. Based on a literature review a small amount of articles have been published on Benzoic acid, 2-(acetyloxy)-5-amino-. This compound has been identified in human blood as reported by (PMID: 31557052 ). Benzoic acid, 2-(acetyloxy)-5-amino- is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Benzoic acid, 2-(acetyloxy)-5-amino- is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

  Mrv1652309112102462D          

 14 14  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 C   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   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 N   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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247698

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1=C(C=C(N)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO4/c1-5(11)14-8-3-2-6(10)4-7(8)9(12)13/h2-4H,10H2,1H3,(H,12,13)

> <INCHI_KEY>
PNKIVCMRLDCYJE-UHFFFAOYSA-N

> <FORMULA>
C9H9NO4

> <MOLECULAR_WEIGHT>
195.174

> <EXACT_MASS>
195.053157774

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.277207437052937

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(acetyloxy)-5-aminobenzoic acid

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
0.07220801979562035

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.192822425386504

> <JCHEM_PKA_STRONGEST_BASIC>
2.920833638127542

> <JCHEM_POLAR_SURFACE_AREA>
89.62

> <JCHEM_REFRACTIVITY>
49.147000000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(acetyloxy)-5-aminobenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8                                                            
CONECT   12    6   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Acetyl-5-asa	HMDB
Acetyl-5-aminosalicylic acid	HMDB

Chemical Formula

C₉H₉NO₄

Average Molecular Weight

195.174

Monoisotopic Molecular Weight

195.053157774

IUPAC Name

2-(acetyloxy)-5-aminobenzoic acid

Traditional Name

2-(acetyloxy)-5-aminobenzoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)OC1=C(C=C(N)C=C1)C(O)=O

InChI Identifier

InChI=1S/C9H9NO4/c1-5(11)14-8-3-2-6(10)4-7(8)9(12)13/h2-4H,10H2,1H3,(H,12,13)

InChI Key

PNKIVCMRLDCYJE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylsalicylic acids. These are o-acylated derivatives of salicylic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Acylsalicylic acids

Alternative Parents

Substituents

Acylsalicylic acid
Aminobenzoic acid
Aminobenzoic acid or derivatives
Phenol ester
Benzoic acid
Phenoxy compound
Benzoyl
Aniline or substituted anilines
Dicarboxylic acid or derivatives
Amino acid or derivatives
Carboxylic acid ester
Amino acid
Carboxylic acid
Carboxylic acid derivative
Organonitrogen compound
Organic nitrogen compound
Amine
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	1.49	ALOGPS
logP	0.072	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	4.19	ChemAxon
pKa (Strongest Basic)	2.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.62 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.15 m³·mol⁻¹	ChemAxon
Polarizability	18.28 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
DeepCCS	[M+H]+	138.48	30932474
DeepCCS	[M-H]-	135.64	30932474
DeepCCS	[M-2H]-	172.004	30932474
DeepCCS	[M+Na]+	147.543	30932474
AllCCS	[M+H]+	142.3	32859911
AllCCS	[M+H-H2O]+	138.2	32859911
AllCCS	[M+NH4]+	146.1	32859911
AllCCS	[M+Na]+	147.2	32859911
AllCCS	[M-H]-	139.6	32859911
AllCCS	[M+Na-2H]-	140.3	32859911
AllCCS	[M+HCOO]-	141.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzoic acid, 2-(acetyloxy)-5-amino-	CC(=O)OC1=C(C=C(N)C=C1)C(O)=O	3181.6	Standard polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-	CC(=O)OC1=C(C=C(N)C=C1)C(O)=O	1933.0	Standard non polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-	CC(=O)OC1=C(C=C(N)C=C1)C(O)=O	1927.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Benzoic acid, 2-(acetyloxy)-5-amino-,2TMS,isomer #1	CC(=O)OC1=CC=C(N[Si](C)(C)C)C=C1C(=O)O[Si](C)(C)C	2012.6	Semi standard non polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,2TMS,isomer #1	CC(=O)OC1=CC=C(N[Si](C)(C)C)C=C1C(=O)O[Si](C)(C)C	2055.4	Standard non polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,2TMS,isomer #1	CC(=O)OC1=CC=C(N[Si](C)(C)C)C=C1C(=O)O[Si](C)(C)C	2358.6	Standard polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,2TMS,isomer #2	CC(=O)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1C(=O)O	1973.3	Semi standard non polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,2TMS,isomer #2	CC(=O)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1C(=O)O	2108.8	Standard non polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,2TMS,isomer #2	CC(=O)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1C(=O)O	2410.8	Standard polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,3TMS,isomer #1	CC(=O)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1C(=O)O[Si](C)(C)C	2003.2	Semi standard non polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,3TMS,isomer #1	CC(=O)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1C(=O)O[Si](C)(C)C	2030.2	Standard non polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,3TMS,isomer #1	CC(=O)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1C(=O)O[Si](C)(C)C	2190.8	Standard polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,2TBDMS,isomer #1	CC(=O)OC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1C(=O)O[Si](C)(C)C(C)(C)C	2426.3	Semi standard non polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,2TBDMS,isomer #1	CC(=O)OC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1C(=O)O[Si](C)(C)C(C)(C)C	2430.2	Standard non polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,2TBDMS,isomer #1	CC(=O)OC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1C(=O)O[Si](C)(C)C(C)(C)C	2557.3	Standard polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,2TBDMS,isomer #2	CC(=O)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1C(=O)O	2457.6	Semi standard non polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,2TBDMS,isomer #2	CC(=O)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1C(=O)O	2471.5	Standard non polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,2TBDMS,isomer #2	CC(=O)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1C(=O)O	2540.1	Standard polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,3TBDMS,isomer #1	CC(=O)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1C(=O)O[Si](C)(C)C(C)(C)C	2629.8	Semi standard non polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,3TBDMS,isomer #1	CC(=O)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1C(=O)O[Si](C)(C)C(C)(C)C	2637.5	Standard non polar	33892256
Benzoic acid, 2-(acetyloxy)-5-amino-,3TBDMS,isomer #1	CC(=O)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1C(=O)O[Si](C)(C)C(C)(C)C	2538.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 2-(acetyloxy)-5-amino- GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udl-3900000000-19c335f0ed4a7b700294	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 2-(acetyloxy)-5-amino- GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 2-(acetyloxy)-5-amino- GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 2-(acetyloxy)-5-amino- GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 2-(acetyloxy)-5-amino- GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 2-(acetyloxy)-5-amino- GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - Benzoic acid, 2-(acetyloxy)-5-amino- 10V, Negative-QTOF	splash10-0f6x-0900000000-3ccaf297f4f42aa46177	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 2-(acetyloxy)-5-amino- 20V, Negative-QTOF	splash10-0pb9-0900000000-d2eca85cd1e183603fc6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 2-(acetyloxy)-5-amino- 40V, Negative-QTOF	splash10-0a4i-2900000000-96955d8edab53a6d6a12	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 2-(acetyloxy)-5-amino- 10V, Positive-QTOF	splash10-0fbj-0900000000-c672ec8ae5b777eea12e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 2-(acetyloxy)-5-amino- 20V, Positive-QTOF	splash10-002r-0900000000-a261f50a38c6f48811f6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 2-(acetyloxy)-5-amino- 40V, Positive-QTOF	splash10-0a4r-4900000000-9989655a05e2d3983cb5	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10702087

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13140652

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Benzoic acid, 2-(acetyloxy)-5-amino- (HMDB0247698)

MOL for HMDB0247698 (Benzoic acid, 2-(acetyloxy)-5-amino-)

3D MOL for HMDB0247698 (Benzoic acid, 2-(acetyloxy)-5-amino-)

3D SDF for HMDB0247698 (Benzoic acid, 2-(acetyloxy)-5-amino-)

3D-SDF for HMDB0247698 (Benzoic acid, 2-(acetyloxy)-5-amino-)

PDB for HMDB0247698 (Benzoic acid, 2-(acetyloxy)-5-amino-)

3D PDB for HMDB0247698 (Benzoic acid, 2-(acetyloxy)-5-amino-)

SMILES for HMDB0247698 (Benzoic acid, 2-(acetyloxy)-5-amino-)

INCHI for HMDB0247698 (Benzoic acid, 2-(acetyloxy)-5-amino-)

Structure for HMDB0247698 (Benzoic acid, 2-(acetyloxy)-5-amino-)

3D Structure for HMDB0247698 (Benzoic acid, 2-(acetyloxy)-5-amino-)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra