(6S,9S,12S,15S,18S,21S)-1-amino-15-(4-aminobutyl)-12-((R)-1-hydroxyethyl)-1-imino-6-(2-mercapto-3-phenylpropanamido)-9,23-dimethyl-18-(2-(methylthio)ethyl)-7,10,13,16,19-pentaoxo-2,8,11,14,17,20-hexaazatetracosane-21-carboxylic acid

ID: ALA1933864

Chembl Id: CHEMBL1933864

PubChem CID: 57395029

Max Phase: Preclinical

Molecular Formula: C39H66N10O9S2

Molecular Weight: 883.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSCC[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)C(S)Cc1ccccc1)[C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(=O)O

Standard InChI:  InChI=1S/C39H66N10O9S2/c1-22(2)20-29(38(57)58)48-35(54)28(16-19-60-5)45-34(53)26(14-9-10-17-40)47-37(56)31(24(4)50)49-32(51)23(3)44-33(52)27(15-11-18-43-39(41)42)46-36(55)30(59)21-25-12-7-6-8-13-25/h6-8,12-13,22-24,26-31,50,59H,9-11,14-21,40H2,1-5H3,(H,44,52)(H,45,53)(H,46,55)(H,47,56)(H,48,54)(H,49,51)(H,57,58)(H4,41,42,43)/t23-,24+,26-,27-,28-,29-,30?,31-/m0/s1

Standard InChI Key:  DDQGCGHRLRYDLV-KIUURDKYSA-N

Alternative Forms

1. Parent:

   

   ALA1933864

   (2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[(3-phenyl-2-sulfanylpropanoyl)amino]pentanoyl]amino]propanoyl]amino]-3-hydroxybutanoyl]amino]hexanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-methylpentanoic 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: 883.15

Molecular Weight (Monoisotopic): 882.4456

AlogP: -0.89

#Rotatable Bonds: 29

Polar Surface Area: 320.05

Molecular Species: ZWITTERION

HBA: 12

HBD: 13

#RO5 Violations: 3

HBA (Lipinski): 19

HBD (Lipinski): 14

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.99

CX Basic pKa: 11.62

CX LogP: -3.49

CX LogD: -5.01

Aromatic Rings: 1

Heavy Atoms: 60

QED Weighted: 0.02

Np Likeness Score: 0.12

References

1. Li B, Cardinale SC, Butler MM, Pai R, Nuss JE, Peet NP, Bavari S, Bowlin TL..  (2011)  Time-dependent botulinum neurotoxin serotype A metalloprotease inhibitors.,  19  (24): [PMID:22082667] [10.1016/j.bmc.2011.10.062]

2. Zhou Y, McGillick BE, Teng YG, Haranahalli K, Ojima I, Swaminathan S, Rizzo RC..  (2016)  Identification of small molecule inhibitors of botulinum neurotoxin serotype E via footprint similarity.,  24  (20): [PMID:27543389] [10.1016/j.bmc.2016.07.031]

Source

Source(1):

• Scientific Literature