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

ID: ALA283758

PubChem CID: 15199910

Max Phase: Preclinical

Molecular Formula: C28H35N4O6P

Molecular Weight: 554.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(CCc1c[nH]c2ccccc12)P(=O)(O)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O

Standard InChI:  InChI=1S/C28H35N4O6P/c1-17(2)13-24(27(33)32-25(28(34)35)14-19-16-30-23-10-6-4-8-21(19)23)31-26(39(36,37)38)12-11-18-15-29-22-9-5-3-7-20(18)22/h3-10,15-17,24-26,29-31H,11-14H2,1-2H3,(H,32,33)(H,34,35)(H2,36,37,38)/t24-,25-,26?/m0/s1

Standard InChI Key:  MIHCJTSHBDWVAV-NPGWBMRXSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA283758

   (2S)-3-(1H-indol-3-yl)-2-[[(2S)-2-[[3-(1H-indol-3-yl)-1-phosphonopropyl]amino]-4-methylpentanoyl]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: 554.58

Molecular Weight (Monoisotopic): 554.2294

AlogP: 3.90

#Rotatable Bonds: 13

Polar Surface Area: 167.54

Molecular Species: ACID

HBA: 4

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -0.61

CX Basic pKa: 6.68

CX LogP: 2.33

CX LogD: -1.63

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.12

Np Likeness Score: 0.13

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