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

ID: ALA279255

PubChem CID: 15221210

Max Phase: Preclinical

Molecular Formula: C21H32N3O6P

Molecular Weight: 453.48

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H32N3O6P/c1-4-7-19(31(28,29)30)23-17(10-13(2)3)20(25)24-18(21(26)27)11-14-12-22-16-9-6-5-8-15(14)16/h5-6,8-9,12-13,17-19,22-23H,4,7,10-11H2,1-3H3,(H,24,25)(H,26,27)(H2,28,29,30)/t17-,18-,19?/m0/s1

Standard InChI Key:  LGRFWMSHOJICKW-ADUPEVMXSA-N

Molfile:  

     RDKit          2D

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    2.1125   -1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2792   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583    1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292    2.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292    1.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -3.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9 13  1  1
 14 11  2  0
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 10 18  1  1
 19  1  1  0
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 29 23  2  0
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  4 14  1  0
 25 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA279255

   3-(S)-1H-Indol-3-yl-2-[(S)-4-methyl-2-(1-phosphono-butylamino)-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: 453.48

Molecular Weight (Monoisotopic): 453.2029

AlogP: 2.59

#Rotatable Bonds: 12

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: -0.61

CX Basic pKa: 6.69

CX LogP: 1.05

CX LogD: -2.91

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: 0.11

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