ID: ALA261634

Max Phase: Preclinical

Molecular Formula: C5H11NO3

Molecular Weight: 133.15

Molecule Type: Small molecule

Representations

Synonyms (1): Iminoribitol
Synonyms from Alternative Forms(1):

Canonical SMILES:  OC[C@H]1NC[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C5H11NO3/c7-2-3-5(9)4(8)1-6-3/h3-9H,1-2H2/t3-,4+,5-/m1/s1

Standard InChI Key:  OQEBIHBLFRADNM-MROZADKFSA-N

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

Properties

Molecular Weight: 133.15

Molecular Weight (Monoisotopic): 133.0739

AlogP: -2.33

#Rotatable Bonds: 1

Polar Surface Area: 72.72

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.32

CX Basic pKa: 9.36

CX LogP: -2.26

CX LogD: -4.20

Aromatic Rings: 0

Heavy Atoms: 9

QED Weighted: 0.32

Np Likeness Score: 2.76

References

1. Minami Y, Kuriyama C, Ikeda K, Kato A, Takebayashi K, Adachi I, Fleet GW, Kettawan A, Okamoto T, Asano N..  (2008)  Effect of five-membered sugar mimics on mammalian glycogen-degrading enzymes and various glucosidases.,  16  (6): [PMID:18258441] [10.1016/j.bmc.2008.01.032]

2. Yasuda K, Kizu H, Yamashita T, Kameda Y, Kato A, Nash RJ, Fleet GW, Molyneux RJ, Asano N..  (2002)  New sugar-mimic alkaloids from the pods of Angylocalyx pynaertii.,  65  (2): [PMID:11858756] [10.1021/np010360f]

3. 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]

4. 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]

5. Bello C, Dal Bello G, Cea M, Nahimana A, Aubry D, Garuti A, Motta G, Moran E, Fruscione F, Pronzato P, Grossi F, Patrone F, Ballestrero A, Dupuis M, Sordat B, Zimmermann K, Loretan J, Wartmann M, Duchosal MA, Nencioni A, Vogel P..  (2011)  Anti-cancer activity of 5-O-alkyl 1,4-imino-1,4-dideoxyribitols.,  19  (24): [PMID:22079865] [10.1016/j.bmc.2011.07.053]

6. Moorthy NS, Brás NF, Ramos MJ, Fernandes PA..  (2012)  Virtual screening and QSAR study of some pyrrolidine derivatives as α-mannosidase inhibitors for binding feature analysis.,  20  (24): [PMID:23151473] [10.1016/j.bmc.2012.10.011]

7. Evans GB, Schramm VL, Tyler PC..  (2018)  The transition to magic bullets - transition state analogue drug design.,  9  (12): [PMID:30627387] [10.1039/C8MD00372F]

Source

Source(1):

• Scientific Literature