1,4-Dideoxy-1,4-imino-N-(4-guanidinobenzyl)-D-ribitol

ID: ALA505234

Chembl Id: CHEMBL505234

PubChem CID: 24813268

Max Phase: Preclinical

Molecular Formula: C13H20N4O3

Molecular Weight: 280.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)Nc1ccc(CN2C[C@H](O)[C@H](O)[C@H]2CO)cc1

Standard InChI:  InChI=1S/C13H20N4O3/c14-13(15)16-9-3-1-8(2-4-9)5-17-6-11(19)12(20)10(17)7-18/h1-4,10-12,18-20H,5-7H2,(H4,14,15,16)/t10-,11+,12-/m1/s1

Standard InChI Key:  ZQFHFKSXRFPQQC-GRYCIOLGSA-N

Alternative Forms

1. Parent:

   

   ALA505234

   1,4-Dideoxy-1,4-imino-N-(4-guanidinobenzyl)-D-ribitol

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: 280.33

Molecular Weight (Monoisotopic): 280.1535

AlogP: -1.11

#Rotatable Bonds: 4

Polar Surface Area: 125.83

Molecular Species: BASE

HBA: 5

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.31

CX Basic pKa: 10.11

CX LogP: -1.17

CX LogD: -4.08

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.31

Np Likeness Score: 0.38

References

1. Goeminne A, McNaughton M, Bal G, Surpateanu G, Van Der Veken P, De Prol S, Versées W, Steyaert J, Haemers A, Augustyns K..  (2008)  Synthesis and biochemical evaluation of guanidino-alkyl-ribitol derivatives as nucleoside hydrolase inhibitors.,  43  (2): [PMID:17582660] [10.1016/j.ejmech.2007.03.027]

2. Berg M, Kohl L, Van der Veken P, Joossens J, Al-Salabi MI, Castagna V, Giannese F, Cos P, Versées W, Steyaert J, Grellier P, Haemers A, Degano M, Maes L, de Koning HP, Augustyns K..  (2010)  Evaluation of nucleoside hydrolase inhibitors for treatment of African trypanosomiasis.,  54  (5): [PMID:20194690] [10.1128/aac.01787-09]

Source

Source(1):

• Scientific Literature