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

ID: ALA277195

PubChem CID: 15221208

Max Phase: Preclinical

Molecular Formula: C27H36N3O6P

Molecular Weight: 529.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(CCCc1ccccc1)P(=O)(O)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O

Standard InChI:  InChI=1S/C27H36N3O6P/c1-18(2)15-23(29-25(37(34,35)36)14-8-11-19-9-4-3-5-10-19)26(31)30-24(27(32)33)16-20-17-28-22-13-7-6-12-21(20)22/h3-7,9-10,12-13,17-18,23-25,28-29H,8,11,14-16H2,1-2H3,(H,30,31)(H,32,33)(H2,34,35,36)/t23-,24-,25?/m0/s1

Standard InChI Key:  RNNSEJBMVQTXDD-JWDFLIAJSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA277195

   (2S)-3-(1H-indol-3-yl)-2-[[(2S)-4-methyl-2-[(4-phenyl-1-phosphonobutyl)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: 529.57

Molecular Weight (Monoisotopic): 529.2342

AlogP: 3.81

#Rotatable Bonds: 14

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: 6.69

CX LogP: 2.63

CX LogD: -1.33

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.17

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]

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