{2-[2-(2-Amino-ethoxy)-ethoxy]-ethyl}-carbamic acid(1S,1aR,8aS)-6-{4-[(S)-1-(cyanomethyl-carbamoyl)-2-phenyl-ethylcarbamoyl]-benzyl}-1,1a,2,3,6,7,8,8a-octahydro-4,5,6-triaza-cyclopenta[a]cyclopropa[e]cycloocten-1-ylmethyl ester

ID: ALA3357964

PubChem CID: 101905671

Max Phase: Preclinical

Molecular Formula: C36H46N8O6

Molecular Weight: 686.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CCNC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccc(Cn2nnc3c2CC[C@H]2[C@@H](CC3)[C@H]2COC(=O)NCCOCCOCCN)cc1

Standard InChI:  InChI=1S/C36H46N8O6/c37-14-16-39-35(46)32(22-25-4-2-1-3-5-25)41-34(45)27-8-6-26(7-9-27)23-44-33-13-11-29-28(10-12-31(33)42-43-44)30(29)24-50-36(47)40-17-19-49-21-20-48-18-15-38/h1-9,28-30,32H,10-13,15-24,38H2,(H,39,46)(H,40,47)(H,41,45)/t28-,29+,30-,32+/m1/s1

Standard InChI Key:  UARIPFCPPRKFOM-BTSHGXIPSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3357964

   [(4S,5S,6R)-12-[[4-[[(2S)-1-(cyanomethylamino)-1-oxo-3-phenylpropan-2-yl]carbamoyl]phenyl]methyl]-10,11,12-triazatricyclo[7.3.0.04,6]dodeca-1(9),10-dien-5-yl]methyl N-[2-[2-(2-aminoethoxy)ethoxy]ethyl]carbamate

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: 686.81

Molecular Weight (Monoisotopic): 686.3540

AlogP: 1.77

#Rotatable Bonds: 18

Polar Surface Area: 195.51

Molecular Species: BASE

HBA: 11

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.83

CX Basic pKa: 9.44

CX LogP: 1.49

CX LogD: -0.52

Aromatic Rings: 3

Heavy Atoms: 50

QED Weighted: 0.11

Np Likeness Score: -0.85

References

1. Wammes AE, Hendriks TG, Amatdjais-Groenen HI, Wijdeven MA, van Hest JC, van Delft FL, Ritschel T, Rutjes FP..  (2014)  Influence of azide incorporation on binding affinity by small papain inhibitors.,  22  (20): [PMID:24972724] [10.1016/j.bmc.2014.06.001]

Source

Source(1):

• Scientific Literature