(2R,3S)-N-(5-Amino-[1,3]dioxan-2-ylmethyl)-3-(1H-indol-3-yl)-2-[2-oxo-3-(3-phenyl-propyl)-imidazolidin-1-yl]-butyramide

ID: ALA147939

Chembl Id: CHEMBL147939

PubChem CID: 44363956

Max Phase: Preclinical

Molecular Formula: C29H37N5O4

Molecular Weight: 519.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](c1c[nH]c2ccccc12)[C@H](C(=O)NC[C@H]1OC[C@H](N)CO1)N1CCN(CCCc2ccccc2)C1=O

Standard InChI:  InChI=1S/C29H37N5O4/c1-20(24-16-31-25-12-6-5-11-23(24)25)27(28(35)32-17-26-37-18-22(30)19-38-26)34-15-14-33(29(34)36)13-7-10-21-8-3-2-4-9-21/h2-6,8-9,11-12,16,20,22,26-27,31H,7,10,13-15,17-19,30H2,1H3,(H,32,35)/t20-,22-,26-,27+/m0/s1

Standard InChI Key:  WSNROJRGRINVPX-IFAMKMIRSA-N

Alternative Forms

1. Parent:

   

   ALA147939

   (2R,3S)-N-(5-Amino-[1,3]dioxan-2-ylmethyl)-3-(1H-indol-3-yl)-2-[2-oxo-3-(3-phenyl-propyl)-imidazolidin-1-yl]-butyramide

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: 519.65

Molecular Weight (Monoisotopic): 519.2846

AlogP: 2.83

#Rotatable Bonds: 10

Polar Surface Area: 112.92

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.49

CX Basic pKa: 9.00

CX LogP: 2.72

CX LogD: 1.12

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.38

Np Likeness Score: -0.35

References

1. Pasternak A, Pan Y, Marino D, Sanderson PE, Mosley R, Rohrer SP, Birzin ET, Huskey SE, Jacks T, Schleim KD, Cheng K, Schaeffer JM, Patchett AA, Yang L..  (1999)  Potent, orally bioavailable somatostatin agonists: good absorption achieved by urea backbone cyclization.,  9  (3): [PMID:10091708] [10.1016/s0960-894x(99)00016-5]

2. Wu YJ, Meanwell NA..  (2021)  Geminal Diheteroatomic Motifs: Some Applications of Acetals, Ketals, and Their Sulfur and Nitrogen Homologues in Medicinal Chemistry and Drug Design.,  64  (14.0): [PMID:34213340] [10.1021/acs.jmedchem.1c00790]

Source

Source(1):

• Scientific Literature