2-[2-(2-{2-[2-(2-Acetylamino-3-carboxy-propionylamino)-4-carboxy-butyrylamino]-3,3-diphenyl-propionylamino}-4-carboxy-butyrylamino)-3-cyclohexyl-propionylamino]-butyric acid

ID: ALA159723

Chembl Id: CHEMBL159723

PubChem CID: 487907

Max Phase: Preclinical

Molecular Formula: C44H58N6O14

Molecular Weight: 894.98

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC[C@H](NC(=O)[C@H](CC1CCCCC1)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)O)NC(C)=O)C(c1ccccc1)c1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C44H58N6O14/c1-3-29(44(63)64)46-41(60)32(23-26-13-7-4-8-14-26)49-39(58)30(19-21-34(52)53)48-43(62)38(37(27-15-9-5-10-16-27)28-17-11-6-12-18-28)50-40(59)31(20-22-35(54)55)47-42(61)33(24-36(56)57)45-25(2)51/h5-6,9-12,15-18,26,29-33,37-38H,3-4,7-8,13-14,19-24H2,1-2H3,(H,45,51)(H,46,60)(H,47,61)(H,48,62)(H,49,58)(H,50,59)(H,52,53)(H,54,55)(H,56,57)(H,63,64)/t29-,30-,31-,32-,33-,38-/m0/s1

Standard InChI Key:  HCCZVIPVSOHWHY-PRSJUXBDSA-N

Alternative Forms

1. Parent:

   

   ALA159723

   2-[2-(2-{2-[2-(2-Acetylamino-3-carboxy-propionylamino)-4-carboxy-butyrylamino]-3,3-diphenyl-propionylamino}-4-carboxy-butyrylamino)-3-cyclohexyl-propionylamino]-butyric acid

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 894.98

Molecular Weight (Monoisotopic): 894.4011

AlogP: 1.42

#Rotatable Bonds: 26

Polar Surface Area: 323.80

Molecular Species: ACID

HBA: 10

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 20

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.25

CX Basic pKa: ┄

CX LogP: 1.01

CX LogD: -11.84

Aromatic Rings: 2

Heavy Atoms: 64

QED Weighted: 0.06

Np Likeness Score: 0.18

References

1. Narjes F, Koehler KF, Koch U, Gerlach B, Colarusso S, Steinkühler C, Brunetti M, Altamura S, De Francesco R, Matassa VG..  (2002)  A designed P1 cysteine mimetic for covalent and non-covalent inhibitors of HCV NS3 protease.,  12  (4): [PMID:11844705] [10.1016/s0960-894x(01)00842-3]

2. Meanwell NA..  (2011)  Synopsis of some recent tactical application of bioisosteres in drug design.,  54  (8): [PMID:21413808] [10.1021/jm1013693]

3. Meanwell NA..  (2018)  Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design.,  61  (14): [PMID:29400967] [10.1021/acs.jmedchem.7b01788]

4. Mei H, Han J, Klika KD, Izawa K, Sato T, Meanwell NA, Soloshonok VA..  (2020)  Applications of fluorine-containing amino acids for drug design.,  186  [PMID:31740056] [10.1016/j.ejmech.2019.111826]

5. Meanwell NA..  (2016)  2015 Philip S. Portoghese Medicinal Chemistry Lectureship. Curing Hepatitis C Virus Infection with Direct-Acting Antiviral Agents: The Arc of a Medicinal Chemistry Triumph.,  59  (16): [PMID:27501244] [10.1021/acs.jmedchem.6b00915]

Source

Source(1):

• Scientific Literature