(3S)-2-[(((3-Amino-3-carboxy)propyl)(hydroxy)phosphinyl)hydroxymethyl]cyclopropane-1-carboxylic Acid

ID: ALA1088873

Max Phase: Preclinical

Molecular Formula: C9H16NO7P

Molecular Weight: 281.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCP(=O)(O)C(O)C1CC1C(=O)O)C(=O)O

Standard InChI:  InChI=1S/C9H16NO7P/c10-6(8(13)14)1-2-18(16,17)9(15)5-3-4(5)7(11)12/h4-6,9,15H,1-3,10H2,(H,11,12)(H,13,14)(H,16,17)/t4?,5?,6-,9?/m0/s1

Standard InChI Key:  USNBSHFADZZDCH-USZIOOFCSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    1.9634    0.8954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9634    0.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2489   -0.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5344    0.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1800   -0.3421    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.2325   -1.0566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925    0.3724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8945   -0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8945   -1.5796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6090   -0.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4340   -0.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0215    0.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0215    1.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360    1.6099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070    1.6099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6778   -0.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3923    0.0704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6778   -1.1671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  5  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  2 16  1  0
 16 17  2  0
 16 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1088873

   ---

2. Alternative Forms:

   

   ALA1088873

   2-[[[(3S)-3-amino-3-carboxypropyl]-hydroxyphosphoryl]-hydroxymethyl]cyclopropane-1-carboxylic acid;hydrochloride

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: 281.20

Molecular Weight (Monoisotopic): 281.0664

AlogP: -0.90

#Rotatable Bonds: 7

Polar Surface Area: 158.15

Molecular Species: ZWITTERION

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.19

CX Basic pKa: 9.53

CX LogP: -3.74

CX LogD: -9.92

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.38

Np Likeness Score: 1.10

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