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

ID: ALA277199

PubChem CID: 10346429

Max Phase: Preclinical

Molecular Formula: C26H34N3O6P

Molecular Weight: 515.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(CCc1ccccc1)P(=O)(O)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O

Standard InChI:  InChI=1S/C26H34N3O6P/c1-17(2)14-22(28-24(36(33,34)35)13-12-18-8-4-3-5-9-18)25(30)29-23(26(31)32)15-19-16-27-21-11-7-6-10-20(19)21/h3-11,16-17,22-24,27-28H,12-15H2,1-2H3,(H,29,30)(H,31,32)(H2,33,34,35)/t22-,23-,24?/m0/s1

Standard InChI Key:  BGHPOLZHWXBMGO-NTZARQNWSA-N

Molfile:  

     RDKit          2D

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 28 24  2  0
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  5 14  1  0
 27 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA277199

   (2S)-3-(1H-indol-3-yl)-2-[[(2S)-4-methyl-2-[(3-phenyl-1-phosphonopropyl)amino]pentanoyl]amino]propanoic 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: 515.55

Molecular Weight (Monoisotopic): 515.2185

AlogP: 3.42

#Rotatable Bonds: 13

Polar Surface Area: 151.75

Molecular Species: ACID

HBA: 4

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -0.61

CX Basic pKa: 6.70

CX LogP: 2.21

CX LogD: -1.74

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.19

Np Likeness Score: 0.09

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]

2. 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