(3R,4S,5R)-5-amino-4-hydroxy-3-(phosphonatooxy)cyclohex-1-ene-1-carboxylate

ID: ALA319727

Cas Number: 135292-59-0

PubChem CID: 192265

Max Phase: Preclinical

Molecular Formula: C7H12NO7P

Molecular Weight: 253.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H]1CC(C(=O)O)=C[C@@H](OP(=O)(O)O)[C@H]1O

Standard InChI:  InChI=1S/C7H12NO7P/c8-4-1-3(7(10)11)2-5(6(4)9)15-16(12,13)14/h2,4-6,9H,1,8H2,(H,10,11)(H2,12,13,14)/t4-,5-,6+/m1/s1

Standard InChI Key:  RPEBFFQWTDZBGR-PBXRRBTRSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
    3.5750   -6.1417    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167   -5.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292   -4.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167   -4.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292   -6.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -6.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292   -3.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -5.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -4.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -6.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -7.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -5.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -3.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4542   -6.1417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292   -6.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167   -3.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  6
  3  4  2  0
  4  2  1  0
  5  2  1  0
  6  1  1  0
  7  3  1  0
  8  5  1  0
  9  8  1  0
 10  1  1  0
 11  1  1  0
 12  1  2  0
 13  7  2  0
  8 14  1  1
  5 15  1  6
 16  7  1  0
  3  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA319727

   (3R,4S,5R)-5-amino-4-hydroxy-3-phosphonooxycyclohexene-1-carboxylic 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: 253.15

Molecular Weight (Monoisotopic): 253.0351

AlogP: -1.43

#Rotatable Bonds: 3

Polar Surface Area: 150.31

Molecular Species: ZWITTERION

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.35

CX Basic pKa: 9.75

CX LogP: -2.96

CX LogD: -7.17

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.38

Np Likeness Score: 1.69

References

1. Marzabadi MR, Font JL, Gruys KJ, Pansegrau PD, Sikorski JA.  (1992)  Design & synthesis of a novel EPSP synthase inhibitor based on its ternary complex with shikimate-3-phosphate and glyphosate,  2  (11): [10.1016/S0960-894X(00)80527-2]

2. Peterson ML, Corey SD, Font JL, Walker MC, Sikorski JA.  (1996)  New simplified inhibitors of EPSP synthase: The importance of ring size for recognition at the shikimate 3-phosphate site,  6  (23): [10.1016/S0960-894X(96)00527-6]

3. Corey SD, Pansegrau PD, Walker MC, Sikorski JA.  (1993)  EPSP synthase inhibitor deisgn III. Synthesis & evaluation of a new 5-oxamic acid analog of EPSP which incorporates a malonate ether as a 3-phosphate mimic,  3  (12): [10.1016/S0960-894X(01)80779-4]

Source

Source(1):

• Scientific Literature