({hydroxy[3-(phosphonooxy)propyl]carbamoyl}methoxy)phosphonic acid

ID: ALA1235276

PubChem CID: 24880023

Max Phase: Preclinical

Molecular Formula: C5H13NO10P2

Molecular Weight: 309.10

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(COP(=O)(O)O)N(O)CCCOP(=O)(O)O

Standard InChI:  InChI=1S/C5H13NO10P2/c7-5(4-16-18(12,13)14)6(8)2-1-3-15-17(9,10)11/h8H,1-4H2,(H2,9,10,11)(H2,12,13,14)

Standard InChI Key:  IISKWLQYGVRJHI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 17  0  0  0  0  0  0  0  0999 V2000
    0.2697    0.1461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4447   -0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1592    0.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8737   -0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0171   -0.6789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3026   -0.2664    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8901   -0.9809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7151    0.4480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882    0.1461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2697    0.9711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9842   -0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9842   -1.0914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6987    0.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4131   -0.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1276    0.1461    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.8421    0.5586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5401   -0.5684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7151    0.8605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
 11  1  1  0
  1 10  1  0
  2  3  1  0
  3  4  1  0
  4  9  1  0
  5  6  1  0
  7  6  2  0
  8  6  1  0
  9  6  1  0
 13 11  1  0
 11 12  2  0
 13 14  1  0
 14 15  1  0
 16 15  2  0
 17 15  1  0
 18 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1235276

   3-{Hydroxy[(phosphonooxy)acetyl]amino}propyl dihydrogen phosphate

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: 309.10

Molecular Weight (Monoisotopic): 309.0015

AlogP: -1.19

#Rotatable Bonds: 8

Polar Surface Area: 174.06

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.17

CX Basic pKa: ┄

CX LogP: -2.50

CX LogD: -9.10

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.16

Np Likeness Score: 0.63

References

1. Daher R, Coinçon M, Fonvielle M, Gest PM, Guerin ME, Jackson M, Sygusch J, Therisod M..  (2010)  Rational design, synthesis, and evaluation of new selective inhibitors of microbial class II (zinc dependent) fructose bis-phosphate aldolases.,  53  (21): [PMID:20929256] [10.1021/jm1009814]

Source

Source(1):

• Scientific Literature