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

ID: ALA282663

PubChem CID: 15199908

Max Phase: Preclinical

Molecular Formula: C26H34N3O7P

Molecular Weight: 531.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(CCc1ccc(O)cc1)P(=O)(O)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O

Standard InChI:  InChI=1S/C26H34N3O7P/c1-16(2)13-22(28-24(37(34,35)36)12-9-17-7-10-19(30)11-8-17)25(31)29-23(26(32)33)14-18-15-27-21-6-4-3-5-20(18)21/h3-8,10-11,15-16,22-24,27-28,30H,9,12-14H2,1-2H3,(H,29,31)(H,32,33)(H2,34,35,36)/t22-,23-,24?/m0/s1

Standard InChI Key:  VPYRQVBWFJEUQC-NTZARQNWSA-N

Molfile:  

     RDKit          2D

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    3.0875   -2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9125   -3.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -3.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4750   -0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167    1.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875    0.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750    0.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0917    2.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0167   -0.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8917   -0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7167   -5.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 13  1  0
  3 10  1  0
  4  1  1  0
  5  7  1  0
  6  3  1  0
  7  2  2  0
  8  4  1  0
  9  6  1  0
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  9 13  1  1
 14 11  2  0
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 16  3  2  0
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 10 18  1  1
 19  4  1  0
 20  1  1  0
 21  1  1  0
 22 12  1  0
 23 25  1  0
 24 27  1  0
 25 19  1  0
 26 28  1  0
 27 29  2  0
 28 23  2  0
 29 23  1  0
 30 24  1  0
 31 11  1  0
 32 18  1  0
 33 14  1  0
 34 32  1  0
 35 32  1  0
 36 31  2  0
 37 36  1  0
 24 26  2  0
  5 14  1  0
 33 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA282663

   (2S)-2-[[(2S)-2-[[3-(4-hydroxyphenyl)-1-phosphonopropyl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)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: 531.55

Molecular Weight (Monoisotopic): 531.2134

AlogP: 3.13

#Rotatable Bonds: 13

Polar Surface Area: 171.98

Molecular Species: ACID

HBA: 5

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -0.61

CX Basic pKa: 6.70

CX LogP: 1.93

CX LogD: -2.01

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.16

Np Likeness Score: 0.22

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