3-(S)-1H-Indol-3-yl-2-[(S)-4-methyl-2-(phosphonomethyl-amino)-pentanoylamino]-propionic acid

ID: ALA281333

PubChem CID: 9953426

Max Phase: Preclinical

Molecular Formula: C18H26N3O6P

Molecular Weight: 411.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NCP(=O)(O)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O

Standard InChI:  InChI=1S/C18H26N3O6P/c1-11(2)7-15(20-10-28(25,26)27)17(22)21-16(18(23)24)8-12-9-19-14-6-4-3-5-13(12)14/h3-6,9,11,15-16,19-20H,7-8,10H2,1-2H3,(H,21,22)(H,23,24)(H2,25,26,27)/t15-,16-/m0/s1

Standard InChI Key:  KORICWMIXKILNW-HOTGVXAUSA-N

Molfile:  

     RDKit          2D

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    4.4292   -1.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -1.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -1.0375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -0.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167   -1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6375   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708   -0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500    0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -0.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -1.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2333   -0.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7542    0.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -2.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167    0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3500   -1.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1958   -1.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -2.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8625    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8292   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375    2.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292    1.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -3.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3875   -3.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 10  1  0
  3 12  1  0
  4  6  1  0
  5  3  1  0
  6  2  2  0
  7  5  1  0
  8  2  1  0
  9  7  1  0
  7 10  1  1
 11  1  1  0
 12 13  1  0
 13 11  1  0
 14  8  2  0
 15  1  2  0
 16  3  2  0
 17  9  2  0
 12 18  1  1
 19  1  1  0
 20  1  1  0
 21  9  1  0
 22  8  1  0
 23 18  1  0
 24 14  1  0
 25 23  1  0
 26 23  1  0
 27 22  2  0
 28 27  1  0
  4 14  1  0
 24 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA281333

   3-(S)-1H-Indol-3-yl-2-[(S)-4-methyl-2-(phosphonomethyl-amino)-pentanoylamino]-propionic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 411.40

Molecular Weight (Monoisotopic): 411.1559

AlogP: 1.42

#Rotatable Bonds: 10

Polar Surface Area: 151.75

Molecular Species: ACID

HBA: 4

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -0.57

CX Basic pKa: 6.50

CX LogP: -0.08

CX LogD: -4.06

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.32

Np Likeness Score: 0.12

References

1. Fukami T, Hayama T, Amano Y, Nakamura Y, Arai Y, Matsuyama K, Yano M, Ishikawa K.  (1994)  Aminophosphonate endothelin converting enzyme inhibitors: potency-enhancing and selectivity-improving modifications of phosphoramidon,  4  (10): [10.1016/S0960-894X(01)80341-3]

Source

Source(1):

• Scientific Literature