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

ID: ALA25269

PubChem CID: 9829399

Max Phase: Preclinical

Molecular Formula: C30H36N3O6P

Molecular Weight: 565.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(CCc1cccc2ccccc12)P(=O)(O)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O

Standard InChI:  InChI=1S/C30H36N3O6P/c1-19(2)16-26(29(34)33-27(30(35)36)17-22-18-31-25-13-6-5-12-24(22)25)32-28(40(37,38)39)15-14-21-10-7-9-20-8-3-4-11-23(20)21/h3-13,18-19,26-28,31-32H,14-17H2,1-2H3,(H,33,34)(H,35,36)(H2,37,38,39)/t26-,27-,28?/m0/s1

Standard InChI Key:  CEWALNPBFDYZAE-ZLBDCPSSSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA25269

   (2S)-3-(1H-indol-3-yl)-2-[[(2S)-4-methyl-2-[(3-naphthalen-1-yl-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: 565.61

Molecular Weight (Monoisotopic): 565.2342

AlogP: 4.57

#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: 6.69

CX LogP: 3.21

CX LogD: -0.74

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.13

Np Likeness Score: 0.03

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