(3S,6R,9S,14aR)-6-((1H-indol-3-yl)methyl)-9-benzyl-3-methyldecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone

ID: ALA525580

Chembl Id: CHEMBL525580

PubChem CID: 44583391

Max Phase: Preclinical

Molecular Formula: C28H31N5O4

Molecular Weight: 501.59

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  C[C@@H]1NC(=O)[C@H]2CCCN2C(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](Cc2c[nH]c3ccccc23)NC1=O

Standard InChI:  InChI=1S/C28H31N5O4/c1-17-25(34)31-22(15-19-16-29-21-11-6-5-10-20(19)21)26(35)32-23(14-18-8-3-2-4-9-18)28(37)33-13-7-12-24(33)27(36)30-17/h2-6,8-11,16-17,22-24,29H,7,12-15H2,1H3,(H,30,36)(H,31,34)(H,32,35)/t17-,22+,23-,24+/m0/s1

Standard InChI Key:  VWVDKFKCFKUUJB-QQJYNPJZSA-N

Alternative Forms

1. Parent:

   

   ALA525580

   cyclo[Ala-D-Trp-Phe-D-Pro]

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: 501.59

Molecular Weight (Monoisotopic): 501.2376

AlogP: 1.43

#Rotatable Bonds: 4

Polar Surface Area: 123.40

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.84

CX Basic pKa: ┄

CX LogP: 1.54

CX LogD: 1.54

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.43

Np Likeness Score: 0.83

References

1. Dolle RE, Michaut M, Martinez-Teipel B, Seida PR, Ajello CW, Muller AL, DeHaven RN, Carroll PJ..  (2009)  Nascent structure-activity relationship study of a diastereomeric series of kappa opioid receptor antagonists derived from CJ-15,208.,  19  (13): [PMID:19464172] [10.1016/j.bmcl.2009.04.105]

2. Smith MT, Kong D, Kuo A, Imam MZ, Williams CM..  (2022)  Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources.,  65  (3.0): [PMID:34995453] [10.1021/acs.jmedchem.0c01915]

Source

Source(1):

• Scientific Literature