(Z)-3-[(4-{Methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino}-phenylamino)-methylene]-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid Methyl Ester

ID: ALA502835

Chembl Id: CHEMBL502835

Max Phase: Approved

First Approval: 2014

Molecular Formula: C31H33N5O4

Molecular Weight: 539.64

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bibf-1120 | Nintedanib | BIBF 1120 | BIBF-1120 | BIBF1120

Synonyms from Alternative Forms(4): Nintedanib ethanesulfonate | Nintedanib esilate | Ofev | Nintedanib esylate

Trade Names(2): Ofev | Vargatef

Canonical SMILES:  COC(=O)c1ccc2c(c1)NC(=O)/C2=C(\Nc1ccc(N(C)C(=O)CN2CCN(C)CC2)cc1)c1ccccc1

Standard InChI:  InChI=1S/C31H33N5O4/c1-34-15-17-36(18-16-34)20-27(37)35(2)24-12-10-23(11-13-24)32-29(21-7-5-4-6-8-21)28-25-14-9-22(31(39)40-3)19-26(25)33-30(28)38/h4-14,19,32H,15-18,20H2,1-3H3,(H,33,38)/b29-28-

Standard InChI Key:  XZXHXSATPCNXJR-ZIADKAODSA-N

Alternative Forms

1. Parent:

   

   ALA502835

   NINTEDANIB

2. Alternative Forms:

   

   ALA502835

   Nintedanib esylate

Molecule Features

Natural Product: No

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: Yes

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 539.64

Molecular Weight (Monoisotopic): 539.2533

AlogP: 3.62

#Rotatable Bonds: 7

Polar Surface Area: 94.22

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.86

CX Basic pKa: 7.23

CX LogP: 2.79

CX LogD: 2.57

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.35

Np Likeness Score: -1.13

References

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Source

Source(10):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• Patent Bioactivity Data
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• Kuster lab chemical proteomics drug profiling
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6