ID: ALA417559

Max Phase: Preclinical

Molecular Formula: C43H56N6O14S

Molecular Weight: 913.02

Molecule Type: Protein

Representations

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

Standard InChI:  InChI=1S/C43H56N6O14S/c1-24(50)44-31(22-35(55)56)41(60)45-29(18-20-34(53)54)39(58)49-37(36(26-13-7-3-8-14-26)27-15-9-4-10-16-27)42(61)46-28(17-19-33(51)52)38(57)47-30(21-25-11-5-2-6-12-25)40(59)48-32(23-64)43(62)63/h3-4,7-10,13-16,25,28-32,36-37,64H,2,5-6,11-12,17-23H2,1H3,(H,44,50)(H,45,60)(H,46,61)(H,47,57)(H,48,59)(H,49,58)(H,51,52)(H,53,54)(H,55,56)(H,62,63)/t28-,29-,30-,31-,32-,37-/m0/s1

Standard InChI Key:  UJAUCRPOZPWCGV-XJJOYFJPSA-N

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

Properties

Molecular Weight: 913.02

Molecular Weight (Monoisotopic): 912.3575

AlogP: 0.94

#Rotatable Bonds: 26

Polar Surface Area: 323.80

Molecular Species: ACID

HBA: 11

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.23

CX Basic pKa:

CX LogP: 0.54

CX LogD: -12.36

Aromatic Rings: 2

Heavy Atoms: 64

QED Weighted: 0.06

Np Likeness Score: 0.21

References

1. Johansson A, Hubatsch I, Akerblom E, Lindeberg G, Winiwarter S, Danielson UH, Hallberg A..  (2001)  Inhibition of hepatitis C virus NS3 protease activity by product-based peptides is dependent on helicase domain.,  11  (2): [PMID:11206459] [10.1016/s0960-894x(00)00625-9]

2. Leung D, Abbenante G, Fairlie DP..  (2000)  Protease inhibitors: current status and future prospects.,  43  (3): [PMID:10669559] [10.1021/jm990412m]

3. 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]

4. Gordon CP, Keller PA..  (2005)  Control of hepatitis C: a medicinal chemistry perspective.,  48  (1): [PMID:15633995] [10.1021/jm0400101]

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

6. 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]

7. 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]

8. 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