(S)-2-((S)-2-((S)-2-((S)-2-(2-aminoacetamido)-3-hydroxypropanamido)-3-(4-(3-phenylpropyl)-1H-1,2,3-triazol-1-yl)propanamido)-3-phenylpropanamido)-4-methylpentanamide

ID: ALA3589129

Chembl Id: CHEMBL3589129

PubChem CID: 86763277

Max Phase: Preclinical

Molecular Formula: C34H47N9O6

Molecular Weight: 677.81

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cn1cc(CCCc2ccccc2)nn1)NC(=O)[C@H](CO)NC(=O)CN)C(N)=O

Standard InChI:  InChI=1S/C34H47N9O6/c1-22(2)16-26(31(36)46)38-32(47)27(17-24-12-7-4-8-13-24)39-33(48)28(40-34(49)29(21-44)37-30(45)18-35)20-43-19-25(41-42-43)15-9-14-23-10-5-3-6-11-23/h3-8,10-13,19,22,26-29,44H,9,14-18,20-21,35H2,1-2H3,(H2,36,46)(H,37,45)(H,38,47)(H,39,48)(H,40,49)/t26-,27-,28-,29-/m0/s1

Standard InChI Key:  VIVIFJSCGWLIIQ-DZUOILHNSA-N

Alternative Forms

1. Parent:

   

   ALA3589129

   (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-hydroxypropanoyl]amino]-3-[4-(3-phenylpropyl)triazol-1-yl]propanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanamide

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: 677.81

Molecular Weight (Monoisotopic): 677.3649

AlogP: -0.88

#Rotatable Bonds: 20

Polar Surface Area: 236.45

Molecular Species: NEUTRAL

HBA: 10

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.34

CX Basic pKa: 7.84

CX LogP: 0.11

CX LogD: -0.46

Aromatic Rings: 3

Heavy Atoms: 49

QED Weighted: 0.08

Np Likeness Score: -0.35

References

1. Zhao F, Darling JE, Gibbs RA, Hougland JL..  (2015)  A new class of ghrelin O-acyltransferase inhibitors incorporating triazole-linked lipid mimetic groups.,  25  (14): [PMID:26009163] [10.1016/j.bmcl.2015.05.009]

2. Iyer, Malliga R., Wood, Casey M., Kunos, George.  (2020)  Recent progress in the discovery of ghrelin O-acyltransferase (GOAT) inhibitors,  11  (10): [PMID:33479618] [10.1039/d0md00210k]

Source

Source(1):

• Scientific Literature