2-{(S)-2-[2-({(S)-1-[(S)-2-((S)-2-Amino-5-guanidino-pentanoylamino)-5-guanidino-pentanoyl]-pyrrolidine-2-carbonyl}-amino)-3-(4-hydroxy-phenyl)-propionylamino]-propionylamino}-4-methyl-pentanoic acid

ID: ALA172313

Chembl Id: CHEMBL172313

PubChem CID: 44384829

Max Phase: Preclinical

Molecular Formula: C35H58N12O8

Molecular Weight: 774.92

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@H](C)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CCCN=C(N)N)C(=O)O

Standard InChI:  InChI=1S/C35H58N12O8/c1-19(2)17-26(33(54)55)46-28(49)20(3)43-30(51)25(18-21-10-12-22(48)13-11-21)45-31(52)27-9-6-16-47(27)32(53)24(8-5-15-42-35(39)40)44-29(50)23(36)7-4-14-41-34(37)38/h10-13,19-20,23-27,48H,4-9,14-18,36H2,1-3H3,(H,43,51)(H,44,50)(H,45,52)(H,46,49)(H,54,55)(H4,37,38,41)(H4,39,40,42)/t20-,23-,24-,25-,26-,27-/m0/s1

Standard InChI Key:  SNRZRTRNGQJTPZ-BCAOEVRMSA-N

Alternative Forms

1. Parent:

   

   ALA172313

   2-{(S)-2-[2-({(S)-1-[(S)-2-((S)-2-Amino-5-guanidino-pentanoylamino)-5-guanidino-pentanoyl]-pyrrolidine-2-carbonyl}-amino)-3-(4-hydroxy-phenyl)-propionylamino]-propionylamino}-4-methyl-pentanoic 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: 774.92

Molecular Weight (Monoisotopic): 774.4501

AlogP: -2.55

#Rotatable Bonds: 22

Polar Surface Area: 349.06

Molecular Species: ZWITTERION

HBA: 10

HBD: 11

#RO5 Violations: 2

HBA (Lipinski): 20

HBD (Lipinski): 16

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.97

CX Basic pKa: 11.20

CX LogP: -5.35

CX LogD: -6.82

Aromatic Rings: 1

Heavy Atoms: 55

QED Weighted: 0.03

Np Likeness Score: 0.25

References

1. Henry JA, Horwell DC, Meecham KG, Rees DC.  (1993)  A structure-affinity study of the amino acid side-chains in neurotensin : N and C terminal deletions and Ala-scan,  3  (5): [10.1016/S0960-894X(00)80698-8]

2. Einsiedel J, Held C, Hervet M, Plomer M, Tschammer N, Hübner H, Gmeiner P..  (2011)  Discovery of highly potent and neurotensin receptor 2 selective neurotensin mimetics.,  54  (8): [PMID:21446649] [10.1021/jm200006c]

Source

Source(1):

• Scientific Literature