(S)-2-((3S,6S,15S,20aS)-3-((1H-indol-3-yl)methyl)-15-((S)-5-guanidino-2-(methylamino)pentanamido)-1,4,9,16-tetraoxoicosahydropyrrolo[1,2-a][1,4,7,12]tetraazacyclooctadecine-6-carboxamido)-4-methylpentanoic acid

ID: ALA4796388

Chembl Id: CHEMBL4796388

PubChem CID: 10440473

Max Phase: Preclinical

Molecular Formula: C40H61N11O8

Molecular Weight: 824.00

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN[C@@H](CCCNC(=N)N)C(=O)N[C@H]1CCCCNC(=O)CC[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)O)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@@H]2CCCN2C1=O

Standard InChI:  InChI=1S/C40H61N11O8/c1-23(2)20-31(39(58)59)50-35(54)28-15-16-33(52)44-17-7-6-12-29(48-34(53)27(43-3)13-8-18-45-40(41)42)38(57)51-19-9-14-32(51)37(56)49-30(36(55)47-28)21-24-22-46-26-11-5-4-10-25(24)26/h4-5,10-11,22-23,27-32,43,46H,6-9,12-21H2,1-3H3,(H,44,52)(H,47,55)(H,48,53)(H,49,56)(H,50,54)(H,58,59)(H4,41,42,45)/t27-,28-,29-,30-,31-,32-/m0/s1

Standard InChI Key:  DPYGZBMJSCYZBF-JNRWAQIZSA-N

Alternative Forms

1. Parent:

   

   ALA4796388

   Me-Arg-Lys(1)-Pro-Trp-Glu(1)-Leu-OH

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 824.00

Molecular Weight (Monoisotopic): 823.4705

AlogP: -0.30

#Rotatable Bonds: 14

Polar Surface Area: 292.83

Molecular Species: ZWITTERION

HBA: 9

HBD: 11

#RO5 Violations: 2

HBA (Lipinski): 19

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.77

CX Basic pKa: 11.98

CX LogP: -2.61

CX LogD: -3.58

Aromatic Rings: 2

Heavy Atoms: 59

QED Weighted: 0.07

Np Likeness Score: 0.41

References

1. Chartier M,Desgagné M,Sousbie M,Côté J,Longpré JM,Marsault E,Sarret P.  (2021)  Design, Structural Optimization, and Characterization of the First Selective Macrocyclic Neurotensin Receptor Type 2 Non-opioid Analgesic.,  64  (4.0): [PMID:33538583] [10.1021/acs.jmedchem.0c01726]

Source

Source(1):

• Scientific Literature