[guanidinomethyl(hydroxy)phosphoryl]methylphosphonic acid

ID: ALA4795079

PubChem CID: 162674093

Max Phase: Preclinical

Molecular Formula: C3H11N3O5P2

Molecular Weight: 231.09

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC(N)=NCP(=O)(O)CP(=O)(O)O

Standard InChI:  InChI=1S/C3H11N3O5P2/c4-3(5)6-1-12(7,8)2-13(9,10)11/h1-2H2,(H,7,8)(H4,4,5,6)(H2,9,10,11)

Standard InChI Key:  OBKMPHPQQSIVNZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 13 12  0  0  0  0  0  0  0  0999 V2000
    3.4999   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2117   -3.5164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9236   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6354   -3.5164    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.3431   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0549   -3.5164    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.7668   -3.9250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0493   -2.6910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0493   -4.3336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6354   -2.6951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6295   -4.3336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7881   -3.5164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4999   -4.7463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  6  9  1  0
  4 10  2  0
  4 11  1  0
  1 12  1  0
  1 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4795079

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 231.09

Molecular Weight (Monoisotopic): 231.0174

AlogP: -1.38

#Rotatable Bonds: 4

Polar Surface Area: 159.23

Molecular Species: ZWITTERION

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -10.99

CX Basic pKa: 11.72

CX LogP: -2.94

CX LogD: -5.13

Aromatic Rings: ┄

Heavy Atoms: 13

QED Weighted: 0.23

Np Likeness Score: 0.53

References

1. Abdelmagid WM,Mahmoodi N,Tanner ME.  (2020)  A guanidinium-based inhibitor of a type I isopentenyl diphosphate isomerase.,  30  (22): [PMID:32979487] [10.1016/j.bmcl.2020.127577]

2. Zhuang Z, Li M, Tanner ME..  (2022)  A guanidinium group is an effective mimic of the tertiary carbocation formed by isopentenyl diphosphate isomerase.,  75  [PMID:36064124] [10.1016/j.bmcl.2022.128971]

Source

Source(1):

• Scientific Literature