(9S,12S,18S)-18,22-diamino-9,12-bis(4-hydroxybenzyl)-8,11,14,17-tetraoxo-7,10,13,16-tetraazadocosan-1-oic acid

ID: ALA1241021

Chembl Id: CHEMBL1241021

PubChem CID: 52940743

Max Phase: Preclinical

Molecular Formula: C32H46N6O8

Molecular Weight: 642.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCCC[C@H](N)C(=O)NCC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)NCCCCCC(=O)O

Standard InChI:  InChI=1S/C32H46N6O8/c33-16-4-3-6-25(34)30(44)36-20-28(41)37-27(19-22-10-14-24(40)15-11-22)32(46)38-26(18-21-8-12-23(39)13-9-21)31(45)35-17-5-1-2-7-29(42)43/h8-15,25-27,39-40H,1-7,16-20,33-34H2,(H,35,45)(H,36,44)(H,37,41)(H,38,46)(H,42,43)/t25-,26-,27-/m0/s1

Standard InChI Key:  OVTWAXKJGCDAAW-QKDODKLFSA-N

Alternative Forms

1. Parent:

   

   ALA1241021

   6-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2,6-diaminohexanoyl]amino]acetyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]hexanoic acid

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: 642.75

Molecular Weight (Monoisotopic): 642.3377

AlogP: 0.19

#Rotatable Bonds: 21

Polar Surface Area: 246.20

Molecular Species: ZWITTERION

HBA: 9

HBD: 9

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.31

CX Basic pKa: 10.34

CX LogP: -2.45

CX LogD: -2.95

Aromatic Rings: 2

Heavy Atoms: 46

QED Weighted: 0.08

Np Likeness Score: 0.22

References

1. Fournel S, Wieckowski S, Sun W, Trouche N, Dumortier H, Bianco A, Chaloin O, Habib M, Peter JC, Schneider P, Vray B, Toes RE, Offringa R, Melief CJ, Hoebeke J, Guichard G..  (2005)  C3-symmetric peptide scaffolds are functional mimetics of trimeric CD40L.,  1  (7): [PMID:16370373] [10.1038/nchembio746]

Source

Source(1):

• Scientific Literature