(S)-2-Amino-2-methyl-3-(3-phosphono-phenyl)-propionic acid

ID: ALA81147

PubChem CID: 44460413

Max Phase: Preclinical

Molecular Formula: C10H14NO5P

Molecular Weight: 259.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@](N)(Cc1cccc(P(=O)(O)O)c1)C(=O)O

Standard InChI:  InChI=1S/C10H14NO5P/c1-10(11,9(12)13)6-7-3-2-4-8(5-7)17(14,15)16/h2-5H,6,11H2,1H3,(H,12,13)(H2,14,15,16)/t10-/m0/s1

Standard InChI Key:  DTADFEAOGGHJNM-JTQLQIEISA-N

Molfile:  

     RDKit          2D

 17 17  0  0  1  0  0  0  0  0999 V2000
    3.5667   -2.2792    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -1.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5500   -2.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5292   -3.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -2.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -2.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -2.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125   -3.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292   -2.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4500   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -3.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625   -3.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -3.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  2  3  1  1
  4  1  1  0
  5  1  2  0
  6  9  1  0
  7  4  1  0
  8  3  2  0
  9  7  2  0
 10  1  1  0
 11  1  1  0
 12  2  1  0
 13  3  1  0
  2 14  1  6
 15  4  2  0
 16 15  1  0
 17 16  2  0
  9 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA81147

   (2S)-2-amino-2-methyl-3-(3-phosphonophenyl)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: 259.20

Molecular Weight (Monoisotopic): 259.0610

AlogP: -0.17

#Rotatable Bonds: 4

Polar Surface Area: 120.85

Molecular Species: ZWITTERION

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.51

CX Basic pKa: 9.69

CX LogP: -2.05

CX LogD: -5.63

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.56

Np Likeness Score: 0.44

References

1. Ma D, Ma Z, Kozikowski AP, Pshenichkin S, Wroblewski JT..  (1998)  Synthesis and biological evaluation of two analogues of (S)-alpha-methyl-3-carboxyphenylalanine.,  8  (18): [PMID:9873559] [10.1016/s0960-894x(98)00409-0]

Source

Source(1):

• Scientific Literature