(S)-3-((4S,7S)-7-(isoquinoline-1-carboxamido)-6,10-dioxo-octahydro-1H-pyridazino[1,2-a][1,2]diazepine-4-carboxamido)-4-oxobutanoic acid

ID: ALA437105

Chembl Id: CHEMBL437105

Cas Number: 192756-07-3

PubChem CID: 9848628

Max Phase: Unknown

Molecular Formula: C24H25N5O7

Molecular Weight: 495.49

Molecule Type: Protein

Names and Identifiers

Synonyms: Vrt-18858 | RU-38384 | RU38384 | VRT18858 | VRT-18858|WV88DU3MUX|VRT18858|192756-07-3|RU38384|RU-38384|UNII-WV88DU3MUX|CHEMBL437105|(3S)-3-((((1S,9S)-Octahydro-9-((1-isoquinolinylcarbonyl)amino)-6,10-dioxo-6H-pyridazino(1,2-a)(1,2)diazepin-1-yl)carbonyl)amino)-4-oxobutanoic acid|Butanoic acid, 3-((((1S,9S)-octahydro-9-((1-isoquinolinylcarbonyl)amino)-6,10-dioxo-6H-pyridazino(1,2-a)(1,2)diazepin-1-yl)carbonyl)amino)-4-oxo-, (3S)-|(S)-3-((1S,9S)-9-(Isoquinoline-1-carboxamido)-6,10-dioxooctahydro-6Show More⌵

Canonical SMILES:  O=C[C@H](CC(=O)O)NC(=O)[C@@H]1CCCN2C(=O)CC[C@H](NC(=O)c3nccc4ccccc34)C(=O)N12

Standard InChI:  InChI=1S/C24H25N5O7/c30-13-15(12-20(32)33)26-22(34)18-6-3-11-28-19(31)8-7-17(24(36)29(18)28)27-23(35)21-16-5-2-1-4-14(16)9-10-25-21/h1-2,4-5,9-10,13,15,17-18H,3,6-8,11-12H2,(H,26,34)(H,27,35)(H,32,33)/t15-,17-,18-/m0/s1

Standard InChI Key:  CUVNEENHHCPUBW-SZMVWBNQSA-N

Alternative Forms

1. Parent:

   

   ALA437105

   VRT-18858

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 495.49

Molecular Weight (Monoisotopic): 495.1754

AlogP: 0.02

#Rotatable Bonds: 7

Polar Surface Area: 166.08

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.81

CX Basic pKa: 2.47

CX LogP: -1.24

CX LogD: -4.33

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.45

Np Likeness Score: -0.14

References

1. Wang Y, O'Neil SV, Wos JA, Oppong KA, Laufersweiler MC, Soper DL, Ellis CD, Baize MW, Fancher AN, Lu W, Suchanek MK, Wang RL, Schwecke WP, Cruze CA, Buchalova M, Belkin M, De B, Demuth TP..  (2007)  Synthesis and evaluation of unsaturated caprolactams as interleukin-1beta converting enzyme (ICE) inhibitors.,  15  (3): [PMID:17127070] [10.1016/j.bmc.2006.11.011]

2. Galatsis P, Caprathe B, Gilmore J, Thomas A, Linn K, Sheehan S, Harter W, Kostlan C, Lunney E, Stankovic C, Rubin J, Brady K, Allen H, Talanian R..  (2010)  Succinic acid amides as P2-P3 replacements for inhibitors of interleukin-1beta converting enzyme (ICE or caspase 1).,  20  (17): [PMID:20656488] [10.1016/j.bmcl.2010.07.004]

3. Baldwin AG, Brough D, Freeman S..  (2016)  Inhibiting the Inflammasome: A Chemical Perspective.,  59  (5): [PMID:26422006] [10.1021/acs.jmedchem.5b01091]

4. Unpublished dataset, 

5. Ulgheri F, Spanu P, Deligia F, Loriga G, Fuggetta MP, de Haan I, Chandgudge A, Groves M, Domling A..  (2022)  Design, synthesis and biological evaluation of 1,5-disubstituted α-amino tetrazole derivatives as non-covalent inflammasome-caspase-1 complex inhibitors with potential application against immune and inflammatory disorders.,  229  [PMID:34823899] [10.1016/j.ejmech.2021.114002]

Source

Source(2):

• Scientific Literature
• Active Ingredient of a Prodrug