NP-MRD: Showing NP-Card for 2-acetamido-3-hydroxybenzoic acid (NP0351470)

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Record Information

Version

2.0

Created at

2025-08-21 02:45:19 UTC

Updated at

2025-08-21 04:00:43 UTC

NP-MRD ID

NP0351470

Natural Product DOI

https://doi.org/10.57994/4517

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-acetamido-3-hydroxybenzoic acid

Description

135891-44-0, Also known as 3-AHAA, 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. 2-acetamido-3-hydroxybenzoic acid was first documented in 2025 (PMID: 40778764). Based on a literature review very few articles have been published on 135891-44-0.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02242319562D          

 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
    0.7145    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
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  2 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0351470

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)NC1=C(O)C=CC=C1C(O)=O

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

> <INCHI_KEY>
HKAWFFIGVUOBQV-UHFFFAOYSA-N

> <FORMULA>
C9H9NO4

> <MOLECULAR_WEIGHT>
195.174

> <EXACT_MASS>
195.053157774

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.28649932294853

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-acetamido-3-hydroxybenzoic acid

> <JCHEM_LOGP>
1.2149737696666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.846085599523503

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.346002209808743

> <JCHEM_PKA_STRONGEST_BASIC>
-4.593928065049501

> <JCHEM_POLAR_SURFACE_AREA>
86.63000000000001

> <JCHEM_REFRACTIVITY>
50.1581

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-acetamido-3-hydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-23         0                                  
HETATM    1  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    3    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    2                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
3-AHAA	MeSH
3-Hydroxy-N-acetylanthranilic acid	MeSH

Chemical Formula

C₉H₉NO₄

Average Mass

195.1740 Da

Monoisotopic Mass

195.05316 Da

IUPAC Name

2-acetamido-3-hydroxybenzoic acid

Traditional Name

2-acetamido-3-hydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)NC1=C(O)C=CC=C1C(O)=O

InChI Identifier

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

InChI Key

HKAWFFIGVUOBQV-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 850 MHz, CD3OD, experimental)	jseyun12@gmail.com	School of Pharmacy, Sungkyunkwan University	Se Yun Jeong	2025-08-21	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces sp. M45		Not Available

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
Hydroxybenzoic acid
Benzoic acid
N-acetylarylamine
Anilide
Benzoyl
N-arylamide
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Acetamide
Vinylogous amide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
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

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	1.21	ChemAxon
pKa (Strongest Acidic)	3.35	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	50.16 m³·mol⁻¹	ChemAxon
Polarizability	18.29 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131922

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jeong SY, He MT, Kim M, Nam KH, Poulsen M, Beemelmanns C, Kang KS, Kim KH: Anti-adipogenic effects of N-acetyltyramine from termite-associated Streptomyces sp. M45. Org Biomol Chem. 2025 Aug 8. doi: 10.1039/d5ob01062d. [PubMed:40778764 ]
DOI: 10.1039/d5ob01062d
PMID: 40778764

Showing NP-Card for 2-acetamido-3-hydroxybenzoic acid (NP0351470)

MOL for NP0351470 (2-acetamido-3-hydroxybenzoic acid)

3D MOL for NP0351470 (2-acetamido-3-hydroxybenzoic acid)

3D SDF for NP0351470 (2-acetamido-3-hydroxybenzoic acid)

3D-SDF for NP0351470 (2-acetamido-3-hydroxybenzoic acid)

PDB for NP0351470 (2-acetamido-3-hydroxybenzoic acid)

3D PDB for NP0351470 (2-acetamido-3-hydroxybenzoic acid)

SMILES for NP0351470 (2-acetamido-3-hydroxybenzoic acid)

INCHI for NP0351470 (2-acetamido-3-hydroxybenzoic acid)

Structure for NP0351470 (2-acetamido-3-hydroxybenzoic acid)

3D Structure for NP0351470 (2-acetamido-3-hydroxybenzoic acid)