1-(3-((2S,5R,8R,11R)-8-(4-aminobutyl)-5-benzyl-11-(4-hydroxy-2,6-dimethylbenzyl)-3,6,9,12-tetraoxo-1,4,7,10-tetraazacyclododecan-2-yl)propyl)guanidine

ID: ALA3976694

PubChem CID: 134152267

Max Phase: Preclinical

Molecular Formula: C32H46N8O5

Molecular Weight: 622.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(O)cc(C)c1C[C@H]1NC(=O)[C@@H](CCCCN)NC(=O)[C@@H](Cc2ccccc2)NC(=O)[C@H](CCCNC(=N)N)NC1=O

Standard InChI:  InChI=1S/C32H46N8O5/c1-19-15-22(41)16-20(2)23(19)18-27-31(45)38-25(12-8-14-36-32(34)35)29(43)39-26(17-21-9-4-3-5-10-21)30(44)37-24(28(42)40-27)11-6-7-13-33/h3-5,9-10,15-16,24-27,41H,6-8,11-14,17-18,33H2,1-2H3,(H,37,44)(H,38,45)(H,39,43)(H,40,42)(H4,34,35,36)/t24-,25+,26-,27-/m1/s1

Standard InChI Key:  RDVGYJZVBMSCFU-HVWQDESWSA-N

Molfile:  

     RDKit          2D

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   14.5969  -12.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.8732  -14.3166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2 20  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA3976694

   ---

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: 622.77

Molecular Weight (Monoisotopic): 622.3591

AlogP: 0.14

#Rotatable Bonds: 12

Polar Surface Area: 224.55

Molecular Species: BASE

HBA: 7

HBD: 9

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.57

CX Basic pKa: 12.16

CX LogP: -0.14

CX LogD: -3.97

Aromatic Rings: 2

Heavy Atoms: 45

QED Weighted: 0.09

Np Likeness Score: 0.64

References

1. Weltrowska G, Nguyen TM, Chung NN, Wood J, Ma X, Guo J, Wilkes BC, Ge Y, Laferrière A, Coderre TJ, Schiller PW..  (2016)  A Cyclic Tetrapeptide ("Cyclodal") and Its Mirror-Image Isomer Are Both High-Affinity μ Opioid Receptor Antagonists.,  59  (19): [PMID:27676089] [10.1021/acs.jmedchem.6b01200]

Source

Source(1):

• Scientific Literature