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

ID: ALA95193

Cas Number: 63959-45-5

PubChem CID: 121947

Max Phase: Preclinical

Molecular Formula: C7H11O8P

Molecular Weight: 254.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C1=C[C@@H](OP(=O)(O)O)[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C7H11O8P/c8-4-1-3(7(10)11)2-5(6(4)9)15-16(12,13)14/h2,4-6,8-9H,1H2,(H,10,11)(H2,12,13,14)/t4-,5-,6+/m1/s1

Standard InChI Key:  QYOJSKGCWNAKGW-PBXRRBTRSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  1  0  0  0  0  0999 V2000
    0.2417   -0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750   -1.2500    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417    0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500   -0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500    2.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750   -0.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625    0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708   -1.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417   -1.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625    2.4708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292    2.4708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -1.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500   -1.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -0.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
  3  4  2  0
  4  1  1  0
  5  1  1  0
  6  3  1  0
  1  7  1  6
  8  5  1  0
  9  8  1  0
 10  2  1  0
 11  2  2  0
 12  6  1  0
 13  6  2  0
 14  2  1  0
  5 15  1  6
  8 16  1  1
  3  9  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA95193

   sodium;[(1R,5R,6S)-3-carboxy-5,6-dihydroxycyclohex-2-en-1-yl] hydrogen phosphate

2. Parent:

   

   ALA95193

   Shikimate-3-phosphate

Molecule Features

Natural Product: Yes

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: 254.13

Molecular Weight (Monoisotopic): 254.0192

AlogP: -1.40

#Rotatable Bonds: 3

Polar Surface Area: 144.52

Molecular Species: ACID

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.32

CX Basic pKa: ┄

CX LogP: -1.76

CX LogD: -8.33

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.39

Np Likeness Score: 1.67

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. Miller MJ, Braccolino DS, Clearly DG, Ream JE, Walker MC, Sikorski JA.  (1994)  EPSP synthase inhibitor design IV. New aromatic substrate analogs and symmetrical inhibitors containing novel 3-phosphate mimics.,  4  (21): [10.1016/S0960-894X(01)80293-6]

3. 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]

4. 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