[2-guanidinoethyl(hydroxy)phosphoryl]methylphosphonic acid

ID: ALA5280439

Max Phase: Preclinical

Molecular Formula: C4H13N3O5P2

Molecular Weight: 245.11

Names and Identifiers

Canonical SMILES:  N=C(N)NCCP(=O)(O)CP(=O)(O)O

Standard InChI:  InChI=1S/C4H13N3O5P2/c5-4(6)7-1-2-13(8,9)3-14(10,11)12/h1-3H2,(H,8,9)(H4,5,6,7)(H2,10,11,12)

Standard InChI Key:  MNWZTJZEYHDOIP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 14 13  0  0  0  0  0  0  0  0999 V2000
   -1.4292   -0.4243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7164   -0.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001   -0.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7128   -0.0029    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421    0.0028    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.8585   -0.4067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1456   -0.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1388    0.8281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095    0.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7162   -0.8281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1456   -0.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1490    0.8106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8585   -0.4301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  2  0
  4 10  2  0
  4 11  1  0
  1 12  1  0
 12 13  2  0
 12 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5280439

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 245.11

Molecular Weight (Monoisotopic): 245.0330

AlogP: -1.12

#Rotatable Bonds: 5

Polar Surface Area: 156.73

Molecular Species: ZWITTERION

HBA: 3

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.23

CX Basic pKa: 12.42

CX LogP: -3.24

CX LogD: -5.27

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.20

Np Likeness Score: 0.35

References

1. 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