2-[(R)-2-((S)-2-Amino-propionylamino)-3-phenyl-propionylamino]-propionic acid

ID: ALA2371837

Cas Number: 155114-42-4

PubChem CID: 7019964

Max Phase: Preclinical

Molecular Formula: C15H21N3O4

Molecular Weight: 307.35

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  C[C@H](N)C(=O)N[C@H](Cc1ccccc1)C(=O)N[C@@H](C)C(=O)O

Standard InChI:  InChI=1S/C15H21N3O4/c1-9(16)13(19)18-12(8-11-6-4-3-5-7-11)14(20)17-10(2)15(21)22/h3-7,9-10,12H,8,16H2,1-2H3,(H,17,20)(H,18,19)(H,21,22)/t9-,10-,12+/m0/s1

Standard InChI Key:  XRUJOVRWNMBAAA-JBLDHEPKSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  1  0  0  0  0  0999 V2000
    4.7771   -0.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0925   -1.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8377   -1.0690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3283    0.5011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0277   -0.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6290    1.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0778    1.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9754    0.0710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5371   -2.4721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4765   -1.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3784    2.6892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8943   -2.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4307    1.7246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4455   -1.4281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6622   -1.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2760    1.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1448   -2.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1068   -1.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4074   -0.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5974   -0.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3050   -1.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0462   -0.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  5  3  1  6
  4  1  1  0
  5  1  1  0
  6  7  1  0
  7  4  1  0
  8  1  2  0
  9  2  2  0
 10  5  1  0
 11  6  2  0
 12  2  1  0
 13  6  1  0
 12 14  1  1
 15 10  1  0
  7 16  1  1
 17 12  1  0
 18 15  1  0
 19 15  2  0
 20 19  1  0
 21 18  2  0
 22 20  2  0
 22 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2371837

   H-Ala-D-Phe-Ala-OH

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: 307.35

Molecular Weight (Monoisotopic): 307.1532

AlogP: -0.35

#Rotatable Bonds: 7

Polar Surface Area: 121.52

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.98

CX Basic pKa: 8.09

CX LogP: -2.26

CX LogD: -2.33

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.55

Np Likeness Score: -0.10

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