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

ID: ALA48981

Chembl Id: CHEMBL48981

Cas Number: 60482-96-4

PubChem CID: 10349413

Max Phase: Preclinical

Molecular Formula: C32H52N8O7

Molecular Weight: 660.82

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](N)CCCN=C(N)N)C(=O)N[C@@H](CC(C)C)C(=O)O

Standard InChI:  InChI=1S/C32H52N8O7/c1-5-19(4)26(29(44)38-24(31(46)47)16-18(2)3)39-27(42)23(17-20-10-12-21(41)13-11-20)37-28(43)25-9-7-15-40(25)30(45)22(33)8-6-14-36-32(34)35/h10-13,18-19,22-26,41H,5-9,14-17,33H2,1-4H3,(H,37,43)(H,38,44)(H,39,42)(H,46,47)(H4,34,35,36)/t19-,22-,23-,24-,25-,26-/m0/s1

Standard InChI Key:  ORFISQWLBSTJAE-KTHKBMNISA-N

Alternative Forms

1. Parent:

   

   ALA48981

   Arg-Pro-Tyr-Ile-Leu

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: 660.82

Molecular Weight (Monoisotopic): 660.3959

AlogP: -0.06

#Rotatable Bonds: 18

Polar Surface Area: 255.56

Molecular Species: ZWITTERION

HBA: 8

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.11

CX Basic pKa: 11.21

CX LogP: -1.27

CX LogD: -1.64

Aromatic Rings: 1

Heavy Atoms: 47

QED Weighted: 0.06

Np Likeness Score: 0.32

References

1. Cain GA, Christos TE, Johnson AL, Pottorf RS, Tam S, Schmidt WK.  (1993)  Identification of simpler analogs of neurotensin(913) which retain antinociceptive activity,  3  (8): [10.1016/S0960-894X(00)80059-1]

2. Lundquist JT, Dix TA..  (1999)  Preparation and receptor binding affinities of cyclic C-terminal neurotensin (8-13) and (9-13) analogues.,  9  (17): [PMID:10498212] [10.1016/s0960-894x(99)00420-5]

3. St-Pierre S, Lalonde JM, Gendreau M, Quirion R, Regoli D, Rioux F..  (1981)  Synthesis of peptides by the solid-phase method. 6. Neurotensin, fragments, and analogues.,  24  (4): [PMID:7265123] [10.1021/jm00136a004]

4. Lundquist JT, Büllesbach EE, Dix TA..  (2000)  Synthesis of neurotensin(9-13) analogues exhibiting enhanced human neurotensin receptor binding affinities.,  10  (5): [PMID:10743946] [10.1016/s0960-894x(00)00018-4]

5. 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]

6. Rivier JE, Lazarus LH, Perrin MH, Brown MR..  (1977)  Neurotensin analogues. Structure--activity relationships.,  20  (11): [PMID:915901] [10.1021/jm00221a011]

Source

Source(1):

• Scientific Literature