ID: ALA425

Max Phase: Approved

First Approval: 1990

Molecular Formula: C14H10N2O6

Molecular Weight: 302.24

Molecule Type: Small molecule

Representations

Synonyms (3): C. i. mordant yellow 5 | Dipentum | Olsalazine
Synonyms from Alternative Forms(3):

Canonical SMILES:  O=C(O)c1cc(/N=N/c2ccc(O)c(C(=O)O)c2)ccc1O

Standard InChI:  InChI=1S/C14H10N2O6/c17-11-3-1-7(5-9(11)13(19)20)15-16-8-2-4-12(18)10(6-8)14(21)22/h1-6,17-18H,(H,19,20)(H,21,22)/b16-15+

Standard InChI Key:  QQBDLJCYGRGAKP-FOCLMDBBSA-N

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

Properties

Molecular Weight: 302.24

Molecular Weight (Monoisotopic): 302.0539

AlogP: 2.91

#Rotatable Bonds: 4

Polar Surface Area: 139.78

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 2.93

CX Basic pKa:

CX LogP: 4.39

CX LogD: -2.49

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.64

Np Likeness Score: -0.10

References

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4. Matsson P, Bergström CA, Nagahara N, Tavelin S, Norinder U, Artursson P..  (2005)  Exploring the role of different drug transport routes in permeability screening.,  48  (2): [PMID:15658873] [10.1021/jm049711o]

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16. 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]

17. Lin X, Skolnik S, Chen X, Wang J..  (2011)  Attenuation of intestinal absorption by major efflux transporters: quantitative tools and strategies using a Caco-2 model.,  39  (2): [PMID:21051535] [10.1124/dmd.110.034629]

18. PubChem BioAssay data set, 

19. WHO Anatomical Therapeutic Chemical Classification, 

20. 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]

21.  (2016)  Nhe3-binding compounds and methods for inhibiting phosphate transport, 

22. Unpublished dataset, 

23. 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]

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26. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

27. Kim M, Ha JH, Choi J, Kim BR, Gapsys V, Lee KO, Jee JG, Chakrabarti KS, de Groot BL, Griesinger C, Ryu KS, Lee D..  (2022)  Repositioning Food and Drug Administration-Approved Drugs for Inhibiting Biliverdin IXβ Reductase B as a Novel Thrombocytopenia Therapeutic Target.,  65  (3.0): [PMID:34957824] [10.1021/acs.jmedchem.1c01664]

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Source

Source(8):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• Patent Bioactivity Data
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6