(3S)-3-[((3-Amino-3-carboxy)propyl)(hydroxy)phosphinyl]-2-methylpropanoic Acid

ID: ALA1092311

PubChem CID: 46884751

Max Phase: Preclinical

Molecular Formula: C8H16NO6P

Molecular Weight: 253.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(CP(=O)(O)CC[C@H](N)C(=O)O)C(=O)O

Standard InChI:  InChI=1S/C8H16NO6P/c1-5(7(10)11)4-16(14,15)3-2-6(9)8(12)13/h5-6H,2-4,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t5?,6-/m0/s1

Standard InChI Key:  XJLAKNBTWHOYHE-GDVGLLTNSA-N

Molfile:  

     RDKit          2D

 16 15  0  0  0  0  0  0  0  0999 V2000
   14.1903  -19.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9048  -18.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6192  -19.2688    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.3338  -18.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6192  -20.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6112  -18.4392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4758  -18.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7614  -19.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0468  -18.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7614  -20.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4758  -18.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0483  -19.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7628  -18.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4772  -19.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7628  -18.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0483  -20.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  3  5  1  0
  8 10  2  0
  2  3  1  0
  7 11  1  1
  3  6  2  0
  4 12  1  0
  1  2  1  0
 12 13  1  0
  1  7  1  0
 13 14  1  0
  3  4  1  0
 13 15  2  0
  7  8  1  0
 12 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1092311

   (3S)-3-[((3-Amino-3-carboxy)propyl)(hydroxy)phosphinyl]-2-methylpropanoic 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: 253.19

Molecular Weight (Monoisotopic): 253.0715

AlogP: -0.22

#Rotatable Bonds: 7

Polar Surface Area: 137.92

Molecular Species: ZWITTERION

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.71

CX Basic pKa: 9.53

CX LogP: -3.17

CX LogD: -9.10

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.46

Np Likeness Score: 0.81

References

1. Selvam C, Oueslati N, Lemasson IA, Brabet I, Rigault D, Courtiol T, Cesarini S, Triballeau N, Bertrand HO, Goudet C, Pin JP, Acher FC..  (2010)  A virtual screening hit reveals new possibilities for developing group III metabotropic glutamate receptor agonists.,  53  (7): [PMID:20218620] [10.1021/jm901523t]

Source

Source(1):

• Scientific Literature