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Showing NP-Card for Aminosalicylic Acid (NP0332008)

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Record Information
Version2.0
Created at2023-10-19 00:00:26 UTC
Updated at2024-09-03 04:17:41 UTC
NP-MRD IDNP0332008
Natural Product DOIhttps://doi.org/10.57994/1131
Secondary Accession NumbersNone
Natural Product Identification
Common NameAminosalicylic Acid
DescriptionAminosalicylic Acid, also known as 4-aminosalicylate or paser, belongs to the class of organic compounds known as aminosalicylic acids. These are salicylic acids carrying an amino group on the benzene ring. An aminobenzoic acid that is salicylic acid substituted by an amino group at position 4. Aminosalicylic Acid is a drug which is used for the treatment of tuberculosis. Aminosalicylic Acid was first documented in 1959 (PMID: 14408481). Aminosalicylic Acid is a moderately basic compound (based on its pKa) (PMID: 13790963) (PMID: 14670340) (PMID: 8444944) (PMID: 5755895) (PMID: 13684569) (PMID: 15494824).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0332008 (Aminosalicylic Acid)

233
  Mrv0541 02231214322D          

 11 11  0  0  0  0            999 V2000
    2.0930    0.4909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.9842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  2  0  0  0  0
  7 10  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
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3D MOL for NP0332008 (Aminosalicylic Acid)

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3D SDF for NP0332008 (Aminosalicylic Acid)
233
  Mrv0541 02231214322D          

 11 11  0  0  0  0            999 V2000
    2.0930    0.4909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.9842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  2  0  0  0  0
  7 10  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332008

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11)

> <INCHI_KEY>
WUBBRNOQWQTFEX-UHFFFAOYSA-N

> <FORMULA>
C7H7NO3

> <MOLECULAR_WEIGHT>
153.1354

> <EXACT_MASS>
153.042593095

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
14.29465219368035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-amino-2-hydroxybenzoic acid

> <ALOGPS_LOGP>
0.62

> <JCHEM_LOGP>
0.82507511626819

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.223689649295505

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.675350131493757

> <JCHEM_PKA_STRONGEST_BASIC>
2.1883174763812283

> <JCHEM_POLAR_SURFACE_AREA>
83.55

> <JCHEM_REFRACTIVITY>
39.9955

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aminosalicylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0332008 (Aminosalicylic Acid)
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PDB for NP0332008 (Aminosalicylic Acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 233                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.907   0.916   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.908   3.226   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.241   3.226   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       6.574  -3.704   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.574   0.916   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.241   0.146   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.574  -2.164   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241  -1.394   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908   0.146   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.908  -1.394   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.574   2.456   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4    7                                                            
CONECT    5    6    9   11                                                  
CONECT    6    1    5    8                                                  
CONECT    7    4    8   10                                                  
CONECT    8    6    7                                                       
CONECT    9    5   10                                                       
CONECT   10    7    9                                                       
CONECT   11    2    3    5                                                  
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0332008 (Aminosalicylic Acid)
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SMILES for NP0332008 (Aminosalicylic Acid)
NC1=CC(O)=C(C=C1)C(O)=O
Download
INCHI for NP0332008 (Aminosalicylic Acid)
InChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11)
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View in JSmol
Synonyms
ValueSource
2-HYDROXY-4-aminobenzoIC ACIDChEBI
4-AminosalicylateChEBI
p-Aminosalicylic acidChEBI
Para-amino salicylic acidChEBI
PASChEBI
PaserChEBI
4-Aminosalicylic acidKegg
PamisylKegg
2-HYDROXY-4-aminobenzoateGenerator
p-AminosalicylateGenerator
Para-amino salicylateGenerator
AminosalicylateGenerator
4-ASAHMDB
Amino-pasHMDB
Aminosalicylate sodiumHMDB
APASHMDB
Para-aminosalicylic acidHMDB
PASKHMDB
4 Aminosalicylic acidHMDB
RezipasHMDB
p-Aminosalicylic acid monolithium saltHMDB
p-Aminosalicylic acid, monosodium salt, dihydrateHMDB
Acid, aminosalicylicHMDB
Alumino 4 aminosalicylic acidHMDB
p Aminosalicylic acid monolithium saltHMDB
p-Aminosalicylic acid monopotassium saltHMDB
p Aminosalicylic acidHMDB
p Aminosalicylic acid monopotassium saltHMDB
p Aminosalicylic acid monosodium saltHMDB
p-Aminosalicylic acid, aluminum (2:1) saltHMDB
Para aminosalicylic acidHMDB
Alumino-4-aminosalicylic acidHMDB
p-Aminosalicylic acid monosodium saltHMDB
p-Aminosalicylic acid, calcium (2:1) saltHMDB
Aminosalicylic acidChEBI
Chemical FormulaC7H7NO3
Average Mass153.1354 Da
Monoisotopic Mass153.04259 Da
IUPAC Name4-amino-2-hydroxybenzoic acid
Traditional Nameaminosalicylic acid
CAS Registry NumberNot Available
SMILES
NC1=CC(O)=C(C=C1)C(O)=O
InChI Identifier
InChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11)
InChI KeyWUBBRNOQWQTFEX-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-19View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-19View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-19View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-19View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-19View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-14View Spectrum
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminosalicylic acids. These are salicylic acids carrying an amino group on the benzene ring.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentAminosalicylic acids  
Alternative Parents
Substituents
  • 4-aminosalicylic acid
    • 

  • Aminosalicylic acid
    • 

  • Salicylic acid
    • 

  • Aminobenzoic acid or derivatives
    • 

  • Aminobenzoic acid
    • 

  • Benzoic acid
    • 

  • Aniline or substituted anilines
    • 

  • M-aminophenol
    • 

  • Aminophenol
    • 

  • Benzoyl
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Vinylogous acid
    • 

  • Amino acid
    • 

  • Amino acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Organic nitrogen compound
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Primary amine
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Amine
    • 

  • 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
logP0.62ALOGPS
logP0.83ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)2.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40 m³·mol⁻¹ChemAxon
Polarizability14.29 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0014378  
DrugBank IDDB00233  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4488  
KEGG Compound IDC02518  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAminosalicylic_Acid  
METLIN IDNot Available
PubChem Compound4649  
PDB IDBHA  
ChEBI ID27565  
Good Scents IDNot Available
References
General References
  1. JUHASZ P, GALAMBOS G: [A simple paper-indicator method for the demonstration of paraaminosalicylic acid (PAS) in urine]. Tuberkulozis. 1961 Jun;14:186-7. [PubMed:13790963  ] 
  2. Iyawoo K: Tuberculosis in Malaysia: problems and prospect of treatment and control. Tuberculosis (Edinb). 2004;84(1-2):4-7. doi: 10.1016/j.tube.2003.08.014. [PubMed:14670340  ] 
  3. Authors unspecified: Controlled trial of short-course regimens of chemotherapy in the ambulatory treatment of spinal tuberculosis. Results at three years of a study in Korea. Twelfth report of the Medical Research Council Working Party on Tuberculosis of the Spine. J Bone Joint Surg Br. 1993 Mar;75(2):240-8. doi: 10.1302/0301-620X.75B2.8444944. [PubMed:8444944  ] 
  4. Tiitinen H, Mattila MJ: Modification of the serum isoniazid levels by different preparations of paraaminosalicylic acid. Arzneimittelforschung. 1968 May;18(5):623-5. [PubMed:5755895  ] 
  5. ARTIS RD, JOHNSON PK, FREE AH: A simplified test for the detection of paraaminosalicylic acid and acetylsalicylic acid metabolites in urine. Am Rev Respir Dis. 1961 Sep;84:435-9. doi: 10.1164/arrd.1961.84.3.435. [PubMed:13684569  ] 
  6. Shah A, Panjabi C, Maurya V, Khanna P: Multidrug resistant miliary tuberculosis and Pott's disease in an immunocompetent patient. Saudi Med J. 2004 Oct;25(10):1468-70. [PubMed:15494824  ] 
  7. NAITO M: [Combined therapy of massive doses of isoniazid, pyrazinamide, and sulfisoxazole for patients with pulmonary tuberculosis resistant to streptomycin, paraaminosalicylic acid, and isoniazid]. Kyoto Daigaku Kekkaku Kenkyusho Kiyo. 1961 Mar;9:136-41. [PubMed:14478036  ] 
  8. KENDIG EL Jr, HUDGENS RO: The effect of rubeola on tuberculosis under antimicrobial therapy. II. Tuberculous meningitis treated with isoniazid, streptomycin and paraaminosalicylic acid. Pediatrics. 1959 Oct;24:619-22. [PubMed:14408481  ] 
  9. Joshi JV, Joshi UM, Sankolli GM, Gupta K, Rao AP, Hazari K, Sheth UK, Saxena BN: A study of interaction of a low-dose combination oral contraceptive with anti-tubercular drugs. Contraception. 1980 Jun;21(6):617-29. doi: 10.1016/0010-7824(80)90034-7. [PubMed:7428368  ] 
  10. MITROIU O, POPA M, NEGREANU W, BILCU M, POPPER M, KAUFMANN S, NICULESCU V, VANCOV Z: [The differential diagnosis of jaundices appearing during treatment with paraaminosalicylic acid (PAS) by means of serum aldolase determination]. Stud Cercet Inframicrobiol. 1960;11:125-31. [PubMed:14423031  ] 
  11. MILLER FF, GREEN RA: Loeffler's syndrome due to paraaminosalicylic acid. Dis Chest. 1962 Jul;42:100-3. doi: 10.1378/chest.42.1.100. [PubMed:14473996  ] 
  12. Miroshnichenko II, Sokolova GB, Mokhireva LV: [Clinical pharmacokinetics of para-aminosalicylic acid tablets]. Antibiot Khimioter. 2009;54(1-2):20-4. [PubMed:19499713  ] 
  13. SCHMITTOVA M, ENGELBERTH O, SRAMKOVA J: [Effect of aminopyrine, paraaminobenzoic acid and paraaminosalicylic acid on experimental carditis in mice]. Cas Lek Cesk. 1959 Oct 30;98:1365-9. [PubMed:14443158  ] 
  14. Wong SC, Ali MA: Hemoglobin E diseases: hematological, analytical, and biosynthetic studies in homozygotes and double heterozygotes for alpha-thalassemia. Am J Hematol. 1982 Aug;13(1):15-21. doi: 10.1002/ajh.2830130104. [PubMed:7137163  ]