(5S,8S,14S,22R)-5,8-dibenzyl-22-((S)-3-(4-hydroxyphenyl)-2-(methylamino)propanamido)-4,7-dimethyl-3,6,9,12,16,23-hexaoxo-1,4,7,10,13,17-hexaazacyclotricosane-14-carboxamide

ID: ALA4087301

PubChem CID: 137641794

Max Phase: Preclinical

Molecular Formula: C44H57N9O9

Molecular Weight: 855.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H]1CCCCNC(=O)C[C@@H](C(N)=O)NC(=O)CNC(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@H](Cc2ccccc2)N(C)C(=O)CNC1=O

Standard InChI:  InChI=1S/C44H57N9O9/c1-46-34(22-30-17-19-31(54)20-18-30)42(60)51-32-16-10-11-21-47-37(55)25-33(40(45)58)50-38(56)26-48-43(61)35(23-28-12-6-4-7-13-28)53(3)44(62)36(24-29-14-8-5-9-15-29)52(2)39(57)27-49-41(32)59/h4-9,12-15,17-20,32-36,46,54H,10-11,16,21-27H2,1-3H3,(H2,45,58)(H,47,55)(H,48,61)(H,49,59)(H,50,56)(H,51,60)/t32-,33+,34+,35+,36+/m1/s1

Standard InChI Key:  GFOOKIKWVLKMJE-WIZSLEGPSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4087301

   ---

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: 855.99

Molecular Weight (Monoisotopic): 855.4279

AlogP: -0.96

#Rotatable Bonds: 10

Polar Surface Area: 261.47

Molecular Species: NEUTRAL

HBA: 10

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.50

CX Basic pKa: 8.31

CX LogP: -1.13

CX LogD: -1.91

Aromatic Rings: 3

Heavy Atoms: 62

QED Weighted: 0.12

Np Likeness Score: 0.52

References

1. Adamska-Bartłomiejczyk A, Janecka A, Szabó MR, Cerlesi MC, Calo G, Kluczyk A, Tömböly C, Borics A..  (2017)  Cyclic mu-opioid receptor ligands containing multiple N-methylated amino acid residues.,  27  (8): [PMID:28318942] [10.1016/j.bmcl.2017.03.016]

Source

Source(1):

• Scientific Literature