ID: ALA1277623

Max Phase: Preclinical

Molecular Formula: C26H32N4O6S2

Molecular Weight: 560.70

Molecule Type: Small molecule

Representations

Canonical SMILES:  N[C@H]1CCSSC[C@@H](C(=O)NCc2ccccc2CC(=O)O)NC(=O)C[C@H](Cc2ccc(O)cc2)NC1=O

Standard InChI:  InChI=1S/C26H32N4O6S2/c27-21-9-10-37-38-15-22(26(36)28-14-18-4-2-1-3-17(18)12-24(33)34)30-23(32)13-19(29-25(21)35)11-16-5-7-20(31)8-6-16/h1-8,19,21-22,31H,9-15,27H2,(H,28,36)(H,29,35)(H,30,32)(H,33,34)/t19-,21-,22-/m0/s1

Standard InChI Key:  VZYRMNZEFCZSER-BVSLBCMMSA-N

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

Properties

Molecular Weight: 560.70

Molecular Weight (Monoisotopic): 560.1763

AlogP: 1.35

#Rotatable Bonds: 7

Polar Surface Area: 170.85

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.18

CX Basic pKa: 8.38

CX LogP: -1.63

CX LogD: -1.66

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.27

Np Likeness Score: 0.57

References

1. Andersson H, Demaegdt H, Vauquelin G, Lindeberg G, Karlén A, Hallberg M, Erdélyi M, Hallberg A..  (2010)  Disulfide cyclized tripeptide analogues of angiotensin IV as potent and selective inhibitors of insulin-regulated aminopeptidase (IRAP).,  53  (22): [PMID:21047126] [10.1021/jm100793t]

2. Mpakali A, Saridakis E, Giastas P, Maben Z, Stern LJ, Larhed M, Hallberg M, Stratikos E..  (2020)  Structural Basis of Inhibition of Insulin-Regulated Aminopeptidase by a Macrocyclic Peptidic Inhibitor.,  11  (7): [PMID:32676150] [10.1021/acsmedchemlett.0c00172]

3. Barlow, Nicholas, Vanga, Sudarsana Reddy, Savmarker, Jonas, Sandstrom, Anja, Burns, Peta, Hallberg, Anders, Aqvist, Johan, Gutierrez-de-Teran, Hugo, Hallberg, Mathias, Larhed, Mats, Chai, Siew Yeen, Thompson, Philip E..  (2020)  Macrocyclic peptidomimetics as inhibitors of insulin-regulated aminopeptidase (IRAP),  11  (2): [PMID:33479630] [10.1039/c9md00485h]

Source

Source(1):

• Scientific Literature