(4S,7R,10S,13R,16S,19R)-10-(4-Amino-butyl)-19-((S)-2-amino-3-phenyl-propionylamino)-16-benzyl-7-((R)-1-hydroxy-ethyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaaza-cycloicosane-4-carboxylic acid

ID: ALA421493

Chembl Id: CHEMBL421493

PubChem CID: 44311993

Max Phase: Preclinical

Molecular Formula: C45H57N9O9S2

Molecular Weight: 932.14

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  C[C@@H](O)[C@H]1NC(=O)[C@H](CCCCN)NC(=O)[C@@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](NC(=O)[C@@H](N)Cc2ccccc2)CSSC[C@H](C(=O)O)NC1=O

Standard InChI:  InChI=1S/C45H57N9O9S2/c1-26(55)38-44(61)53-37(45(62)63)25-65-64-24-36(52-39(56)31(47)20-27-12-4-2-5-13-27)43(60)50-34(21-28-14-6-3-7-15-28)41(58)51-35(22-29-23-48-32-17-9-8-16-30(29)32)42(59)49-33(40(57)54-38)18-10-11-19-46/h2-9,12-17,23,26,31,33-38,48,55H,10-11,18-22,24-25,46-47H2,1H3,(H,49,59)(H,50,60)(H,51,58)(H,52,56)(H,53,61)(H,54,57)(H,62,63)/t26-,31+,33+,34+,35-,36+,37-,38-/m1/s1

Standard InChI Key:  KDRDDUWNTUSPFR-IAGZALEMSA-N

Alternative Forms

1. Parent:

   

   ALA421493

   (4S,7R,10S,13R,16S,19R)-10-(4-Amino-butyl)-19-((S)-2-amino-3-phenyl-propionylamino)-16-benzyl-7-((R)-1-hydroxy-ethyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaaza-cycloicosane-4-carboxylic acid

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: 932.14

Molecular Weight (Monoisotopic): 931.3721

AlogP: 0.42

#Rotatable Bonds: 14

Polar Surface Area: 299.96

Molecular Species: ZWITTERION

HBA: 12

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.42

CX Basic pKa: 10.19

CX LogP: -2.02

CX LogD: -2.45

Aromatic Rings: 4

Heavy Atoms: 65

QED Weighted: 0.06

Np Likeness Score: 0.85

References

1. Osapay G, Prokai L, Kim HS, Medzihradszky KF, Coy DH, Liapakis G, Reisine T, Melacini G, Zhu Q, Wang SH, Mattern RH, Goodman M..  (1997)  Lanthionine-somatostatin analogs: synthesis, characterization, biological activity, and enzymatic stability studies.,  40  (14): [PMID:9216843] [10.1021/jm960850i]

2. Melacini G, Zhu Q, Osapay G, Goodman M..  (1997)  A refined model for the somatostatin pharmacophore: conformational analysis of lanthionine-sandostatin analogs.,  40  (14): [PMID:9216844] [10.1021/jm960851a]

Source

Source(1):

• Scientific Literature