2-((3S,6S,9S,12S,15R)-15-((2S,3R)-2-((S)-2-((S)-2-amino-3-(4-hydroxyphenyl)propanamido)-3-hydroxypropanamido)-3-hydroxybutanamido)-9-benzyl-6-sec-butyl-3-(2-(methylthio)ethyl)-2,5,8,11,14-pentaoxo-1-thia-4,7,10,13-tetraazacyclohexadecan-12-yl)acetic acid

ID: ALA2337554

Chembl Id: CHEMBL2337554

PubChem CID: 10306730

Max Phase: Preclinical

Molecular Formula: C43H60N8O13S2

Molecular Weight: 961.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](CC(=O)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@@H](N)Cc2ccc(O)cc2)[C@@H](C)O)CSC(=O)[C@H](CCSC)NC1=O

Standard InChI:  InChI=1S/C43H60N8O13S2/c1-5-22(2)34-41(62)45-28(15-16-65-4)43(64)66-21-32(40(61)47-30(19-33(55)56)37(58)46-29(38(59)50-34)18-24-9-7-6-8-10-24)49-42(63)35(23(3)53)51-39(60)31(20-52)48-36(57)27(44)17-25-11-13-26(54)14-12-25/h6-14,22-23,27-32,34-35,52-54H,5,15-21,44H2,1-4H3,(H,45,62)(H,46,58)(H,47,61)(H,48,57)(H,49,63)(H,50,59)(H,51,60)(H,55,56)/t22-,23+,27-,28-,29-,30-,31-,32-,34-,35-/m0/s1

Standard InChI Key:  QPIROHVZMLYRNN-YRNJLPRFSA-N

Alternative Forms

1. Parent:

   

   ALA2337554

   Autoinducing Peptide I

Molecule Features

Natural Product: Yes

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: 961.13

Molecular Weight (Monoisotopic): 960.3721

AlogP: -2.18

#Rotatable Bonds: 19

Polar Surface Area: 344.78

Molecular Species: ACID

HBA: 15

HBD: 12

#RO5 Violations: 3

HBA (Lipinski): 21

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.80

CX Basic pKa: 7.73

CX LogP: -3.82

CX LogD: -3.96

Aromatic Rings: 2

Heavy Atoms: 66

QED Weighted: 0.07

Np Likeness Score: 0.75

References

1. Gordon CP, Williams P, Chan WC..  (2013)  Attenuating Staphylococcus aureus virulence gene regulation: a medicinal chemistry perspective.,  56  (4): [PMID:23294220] [10.1021/jm3014635]

2. Gordon CP, Olson SD, Lister JL, Kavanaugh JS, Horswill AR..  (2016)  Truncated Autoinducing Peptides as Antagonists of Staphylococcus lugdunensis Quorum Sensing.,  59  (19): [PMID:27585401] [10.1021/acs.jmedchem.6b00727]

3. Horswill AR, Gordon CP..  (2020)  Structure-Activity Relationship Studies of Small Molecule Modulators of the Staphylococcal Accessory Gene Regulator.,  63  (6): [PMID:31658413] [10.1021/acs.jmedchem.9b00798]

Source

Source(1):

• Scientific Literature