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Showing NP-Card for p-(Acetylamino)benzoic acid (NP0080043)

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Record Information
Version2.0
Created at2022-04-29 01:05:49 UTC
Updated at2022-04-29 01:05:49 UTC
NP-MRD IDNP0080043
Secondary Accession NumbersNone
Natural Product Identification
Common Namep-(Acetylamino)benzoic acid
DescriptionAcedoben, also known as N-acetyl-paba, belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group. Acedoben is an extremely weak basic (essentially neutral) compound (based on its pKa). p-(Acetylamino)benzoic acid is found in Streptomyces venezuelae. p-(Acetylamino)benzoic acid was first documented in 1995 (PMID: 7585581). A amidobenzoic acid that consists of benzoic acid bearing an acetamido substituent at position 4 (PMID: 11808848).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0080043 (p-(Acetylamino)benzoic acid)


  Mrv0541 02231217432D          

 13 13  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   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   -1.2375    0.0000 N   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
    1.4289    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   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  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
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
Download

3D MOL for NP0080043 (p-(Acetylamino)benzoic acid)

     RDKit          3D

 22 22  0  0  0  0  0  0  0  0999 V2000
    4.2491    0.2249   -0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7679    0.4974   -0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    1.4892   -0.9446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8382   -0.3439    0.3724 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4470   -0.1766    0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1925    0.8026   -0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5824    0.9127   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3596    0.0191    0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8313    0.0961    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3583    1.0220   -0.4037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5365   -0.8438    0.9802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6975   -0.9633    0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3389   -1.0996    1.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6219    0.9885    0.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7114    0.3394   -1.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4298   -0.8070    0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2398   -1.1678    0.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3630    1.5305   -0.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0576    1.7127   -1.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0052   -0.6693    1.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3246   -1.6704    1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1154   -1.8936    1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8 12  1  0
 12 13  2  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
 13  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
 12 21  1  0
 13 22  1  0
 11 20  1  0
M  END
Download

3D SDF for NP0080043 (p-(Acetylamino)benzoic acid)


  Mrv0541 02231217432D          

 13 13  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   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   -1.2375    0.0000 N   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
    1.4289    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   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  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
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0080043

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)NC1=CC=C(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO3/c1-6(11)10-8-4-2-7(3-5-8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13)

> <INCHI_KEY>
QCXJEYYXVJIFCE-UHFFFAOYSA-N

> <FORMULA>
C9H9NO3

> <MOLECULAR_WEIGHT>
179.1727

> <EXACT_MASS>
179.058243159

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
17.816692417205495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-acetamidobenzoic acid

> <ALOGPS_LOGP>
1.14

> <JCHEM_LOGP>
0.8685390913333331

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.720799511002443

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.161065184374958

> <JCHEM_PKA_STRONGEST_BASIC>
-4.418829382441783

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
48.1772

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-acetamidobenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0080043 (p-(Acetylamino)benzoic acid)

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PDB for NP0080043 (p-(Acetylamino)benzoic acid)
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  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667   4.620   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                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0080043 (p-(Acetylamino)benzoic acid)
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SMILES for NP0080043 (p-(Acetylamino)benzoic acid)
CC(=O)NC1=CC=C(C=C1)C(O)=O
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INCHI for NP0080043 (p-(Acetylamino)benzoic acid)
InChI=1S/C9H9NO3/c1-6(11)10-8-4-2-7(3-5-8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13)
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View in JSmol
Synonyms
ValueSource
4-(Acetylamino)benzoic acidChEBI
4-Acetylaminobenzoic acidChEBI
4-CarboxyacetanilideChEBI
AcedobeneChEBI
AcedobenumChEBI
N-Acetyl-p-aminobenzoic acidChEBI
N-Acetyl-pabaChEBI
p-Acetamidobenzoic acidChEBI
p-Acetoaminobenzoic acidChEBI
p-Acetylaminobenzoic acidChEBI
PARA acetamido benzoIC ACIDChEBI
4-(Acetylamino)benzoateGenerator
4-AcetylaminobenzoateGenerator
N-Acetyl-p-aminobenzoateGenerator
p-AcetamidobenzoateGenerator
p-AcetoaminobenzoateGenerator
p-AcetylaminobenzoateGenerator
PARA acetamido benzoateGenerator
AcedobenChEBI, MeSH
4-AcetamidobenzoateGenerator
4-Acetamidobenzoic acid, sodium saltMeSH
Acetyl-P-aminobenzoic acidMeSH
PACBAMeSH
Para-acetamidobenzoic acidMeSH
FibrodermMeSH
Chemical FormulaC9H9NO3
Average Mass179.1727 Da
Monoisotopic Mass179.05824 Da
IUPAC Name4-acetamidobenzoic acid
Traditional Name4-acetamidobenzoic acid
CAS Registry NumberNot Available
SMILES
CC(=O)NC1=CC=C(C=C1)C(O)=O
InChI Identifier
InChI=1S/C9H9NO3/c1-6(11)10-8-4-2-7(3-5-8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13)
InChI KeyQCXJEYYXVJIFCE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces venezuelaeBacteria
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentBenzoic acids  
Alternative Parents
Substituents
  • Benzoic acid
    • 

  • Benzoyl
    • 

  • Carboximidic acid
    • 

  • Carboximidic acid derivative
    • 

  • Carboxylic acid derivative
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic nitrogen compound
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.14ALOGPS
logP0.87ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.18 m³·mol⁻¹ChemAxon
Polarizability17.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB04500  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcedoben  
METLIN IDNot Available
PubChem Compound19266  
PDB IDNot Available
ChEBI ID46171  
Good Scents IDNot Available
References
General References
  1. Chang CC, Hsieh YY, Chung JG, Tsai HD, Tsai CH: Leukemia inhibitory factor decreases the arylamine N-acetyltransferase activity in human cumulus granulosa cells. J Assist Reprod Genet. 2001 Dec;18(12):660-4. doi: 10.1023/a:1013167317997. [PubMed:11808848  ] 
  2. Badawi AF, Hirvonen A, Bell DA, Lang NP, Kadlubar FF: Role of aromatic amine acetyltransferases, NAT1 and NAT2, in carcinogen-DNA adduct formation in the human urinary bladder. Cancer Res. 1995 Nov 15;55(22):5230-7. [PubMed:7585581  ]