[2,2-dimethyl-3-(N-(4-cyanobenzoyl)aminoi)-5-phenylpentanoic anhydride]

ID: ALA108540

PubChem CID: 10394816

Max Phase: Preclinical

Molecular Formula: C42H42N4O5

Molecular Weight: 682.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C(=O)OC(=O)C(C)(C)C(CCc1ccccc1)NC(=O)c1ccc(C#N)cc1)C(CCc1ccccc1)NC(=O)c1ccc(C#N)cc1

Standard InChI:  InChI=1S/C42H42N4O5/c1-41(2,35(25-19-29-11-7-5-8-12-29)45-37(47)33-21-15-31(27-43)16-22-33)39(49)51-40(50)42(3,4)36(26-20-30-13-9-6-10-14-30)46-38(48)34-23-17-32(28-44)18-24-34/h5-18,21-24,35-36H,19-20,25-26H2,1-4H3,(H,45,47)(H,46,48)

Standard InChI Key:  HQNCLEFIYXURJH-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA108540

   2-(4-Cyanophenylcarboxamido)-1,1-dimethyl-4-phenylpentanoic anhydride

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 682.82

Molecular Weight (Monoisotopic): 682.3155

AlogP: 6.71

#Rotatable Bonds: 14

Polar Surface Area: 149.15

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 8.60

CX LogD: 8.60

Aromatic Rings: 4

Heavy Atoms: 51

QED Weighted: 0.11

Np Likeness Score: -0.29

References

1. Iijima K, Katada J, Yasuda E, Uno I, Hayashi Y..  (1999)  N-[2,2-dimethyl-3-(N-(4-cyanobenzoyl)amino)nonanoyl]-L-phenylalanine ethyl ester as a stable ester-type inhibitor of chymotrypsin-like serine proteases: structural requirements for potent inhibition of alpha-chymotrypsin.,  42  (2): [PMID:9925737] [10.1021/jm980562h]

2. Iijima K, Katada J, Hayashi Y..  (1999)  Symmetrical anhydride-type serine protease inhibitors: structure-activity relationship studies of human chymase inhibitors.,  9  (3): [PMID:10091694] [10.1016/s0960-894x(99)00012-8]

Source

Source(1):

• Scientific Literature