(S)-2-({(S)-1-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-methyl-pentanoic acid

ID: ALA2371839

PubChem CID: 11326774

Max Phase: Preclinical

Molecular Formula: C20H29N3O5

Molecular Weight: 391.47

Molecule Type: Protein

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H29N3O5/c1-3-12(2)17(20(27)28)22-18(25)16-5-4-10-23(16)19(26)15(21)11-13-6-8-14(24)9-7-13/h6-9,12,15-17,24H,3-5,10-11,21H2,1-2H3,(H,22,25)(H,27,28)/t12-,15-,16-,17-/m0/s1

Standard InChI Key:  SOEGLGLDSUHWTI-STECZYCISA-N

Molfile:  

     RDKit          2D

 28 29  0  0  1  0  0  0  0  0999 V2000
    4.3000    0.0333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -1.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -1.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625    0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6875    1.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -1.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500    0.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -3.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5750    0.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -0.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250    0.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -2.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792   -0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -0.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750   -0.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042    0.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500   -0.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4042    0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4000   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  5  3  1  1
  4  3  1  0
  5  1  1  0
  6  4  1  1
  7  6  1  0
  8  2  1  0
  9  2  2  0
 10  3  2  0
 11  8  1  0
 12  7  2  0
 13  1  1  0
  8 14  1  1
 15  6  1  0
 16 11  1  0
 17  7  1  0
 18 21  1  0
 19 16  2  0
 20 16  1  0
 21 20  2  0
 22 19  1  0
 23  5  1  0
 24 18  1  0
 25 13  1  0
 26 15  1  0
 15 27  1  6
 28 26  1  0
 25 23  1  0
 18 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2371839

   Tyr-Pro-Ile

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: 391.47

Molecular Weight (Monoisotopic): 391.2107

AlogP: 0.87

#Rotatable Bonds: 8

Polar Surface Area: 132.96

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.04

CX Basic pKa: 7.72

CX LogP: -0.96

CX LogD: -1.11

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -0.07

References

1. Biegel A, Gebauer S, Hartrodt B, Brandsch M, Neubert K, Thondorf I..  (2005)  Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter PEPT1.,  48  (13): [PMID:15974593] [10.1021/jm048982w]

Source

Source(1):

• Scientific Literature