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

ID: ALA344337

Chembl Id: CHEMBL344337

PubChem CID: 44363448

Max Phase: Preclinical

Molecular Formula: C40H66N12O9

Molecular Weight: 859.04

Molecule Type: Protein

Names and Identifiers

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

Standard InChI:  InChI=1S/C40H66N12O9/c1-6-23(4)32(36(58)50-30(38(60)61)20-22(2)3)51-34(56)29(21-25-13-15-26(54)16-14-25)49-35(57)31-12-9-19-52(31)37(59)28(11-8-18-46-40(43)44)48-33(55)27(47-24(5)53)10-7-17-45-39(41)42/h13-16,22-23,27-32,54H,6-12,17-21H2,1-5H3,(H,47,53)(H,48,55)(H,49,57)(H,50,58)(H,51,56)(H,60,61)(H4,41,42,45)(H4,43,44,46)/t23-,27+,28+,29+,30+,31+,32+/m1/s1

Standard InChI Key:  ZUADVYNSAVMKLJ-CUICDERCSA-N

Alternative Forms

1. Parent:

   

   ALA344337

   (S)-2-((2S,3R)-2-((S)-2-((S)-1-((S)-2-((S)-2-acetamido-5-guanidinopentanamido)-5-guanidinopentanoyl)pyrrolidine-2-carboxamido)-3-(4-hydroxyphenyl)propanamido)-3-methylpentanamido)-4-methylpentanoic 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: 859.04

Molecular Weight (Monoisotopic): 858.5076

AlogP: -0.93

#Rotatable Bonds: 25

Polar Surface Area: 347.14

Molecular Species: ZWITTERION

HBA: 10

HBD: 13

#RO5 Violations: 2

HBA (Lipinski): 21

HBD (Lipinski): 15

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.11

CX Basic pKa: 11.87

CX LogP: -4.89

CX LogD: -5.11

Aromatic Rings: 1

Heavy Atoms: 61

QED Weighted: 0.03

Np Likeness Score: 0.07

References

1. Lundquist JT, Dix TA..  (1999)  Synthesis and human neurotensin receptor binding activities of neurotensin(8-13) analogues containing position 8 alpha-azido-N-alkylated derivatives of ornithine, lysine, and homolysine.,  42  (23): [PMID:10579853] [10.1021/jm9903444]

2. 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]

3. Orwig KS, Lassetter MR, Hadden MK, Dix TA..  (2009)  Comparison of N-terminal modifications on neurotensin(8-13) analogues correlates peptide stability but not binding affinity with in vivo efficacy.,  52  (7): [PMID:19290594] [10.1021/jm801072v]

Source

Source(1):

• Scientific Literature