5-[4-(2-Carboxy-ethylcarbamoyl)-phenylazo]-2-hydroxy-benzoic acid (Balsalazide)

ID: ALA1201346

Chembl Id: CHEMBL1201346

Max Phase: Approved

First Approval: 2000

Molecular Formula: C17H15N3O6

Molecular Weight: 357.32

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Balsalazide

Synonyms from Alternative Forms(12): Balsalazide sodium | Balsalazide disodium salt dihydrate | Balsalazide disodium | Balsalazide disodium anhydrous | Balsalazide disodium dihydrate | Balsalazine | BX-661A | BX661A | NSC-760046 | Colazal | Colazide | Giazo

Canonical SMILES:  O=C(O)CCNC(=O)c1ccc(/N=N/c2ccc(O)c(C(=O)O)c2)cc1

Standard InChI:  InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,21H,7-8H2,(H,18,24)(H,22,23)(H,25,26)/b20-19+

Standard InChI Key:  IPOKCKJONYRRHP-FMQUCBEESA-N

Alternative Forms

1. Alternative Forms:

   

   ALA1201346

   Balsalazide disodium

2. Parent:

   

   ALA1201346

   BALSALAZIDE

Molecule Features

Natural Product: No

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: Yes

Calculated Properties

Molecular Weight: 357.32

Molecular Weight (Monoisotopic): 357.0961

AlogP: 2.71

#Rotatable Bonds: 7

Polar Surface Area: 148.65

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.06

CX Basic pKa: ┄

CX LogP: 3.17

CX LogD: -3.62

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.56

Np Likeness Score: -0.50

References

1. Carceller E, Salas J, Merlos M, Giral M, Ferrando R, Escamilla I, Ramis J, García-Rafanell J, Forn J..  (2001)  Novel azo derivatives as prodrugs of 5-aminosalicylic acid and amino derivatives with potent platelet activating factor antagonist activity.,  44  (18): [PMID:11520209] [10.1021/jm010852p]

2. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

3. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  7  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]

4. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. WHO Anatomical Therapeutic Chemical Classification, 

8. DrugMatrix,  [10.6019/CHEMBL3885881]

9. Chen M, Suzuki A, Thakkar S, Yu K, Hu C, Tong W..  (2016)  DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.,  21  (4): [PMID:26948801] [10.1016/j.drudis.2016.02.015]

10. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]

11. Glas C,Dietschreit JCB,Wössner N,Urban L,Ghazy E,Sippl W,Jung M,Ochsenfeld C,Bracher F.  (2020)  Identification of the subtype-selective Sirt5 inhibitor balsalazide through systematic SAR analysis and rationalization via theoretical investigations.,  206  [PMID:32858418] [10.1016/j.ejmech.2020.112676]

12. Yang F, Su H, Deng J, Mou L, Wang H, Li R, Dai QQ, Yan YH, Qian S, Wang Z, Li GB, Yang L..  (2021)  Discovery of new human Sirtuin 5 inhibitors by mimicking glutaryl-lysine substrates.,  225  [PMID:34461505] [10.1016/j.ejmech.2021.113803]

13. Glas C, Naydenova E, Lechner S, Wössner N, Yang L, Dietschreit JCB, Sun H, Jung M, Kuster B, Ochsenfeld C, Bracher F..  (2022)  Development of hetero-triaryls as a new chemotype for subtype-selective and potent Sirt5 inhibition.,  240  [PMID:35853430] [10.1016/j.ejmech.2022.114594]

14. Fiorentino F, Castiello C, Mai A, Rotili D..  (2022)  Therapeutic Potential and Activity Modulation of the Protein Lysine Deacylase Sirtuin 5.,  65  (14.0): [PMID:35802779] [10.1021/acs.jmedchem.2c00687]

15. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• DrugMatrix
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21