N-Benzyl-1,4-dideoxy-1,4-imino-D-ribitol

ID: ALA1169558

Chembl Id: CHEMBL1169558

PubChem CID: 44606291

Max Phase: Preclinical

Molecular Formula: C12H17NO3

Molecular Weight: 223.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1[C@@H](O)[C@@H](O)CN1Cc1ccccc1

Standard InChI:  InChI=1S/C12H17NO3/c14-8-10-12(16)11(15)7-13(10)6-9-4-2-1-3-5-9/h1-5,10-12,14-16H,6-8H2/t10-,11-,12+/m0/s1

Standard InChI Key:  SBDAWMSBMQBJRA-SDDRHHMPSA-N

Alternative Forms

1. Parent:

   

   ALA1169558

   (2S,3R,4S)-1-benzyl-2-(hydroxymethyl)pyrrolidine-3,4-diol

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: 223.27

Molecular Weight (Monoisotopic): 223.1208

AlogP: -0.42

#Rotatable Bonds: 3

Polar Surface Area: 63.93

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.31

CX Basic pKa: 8.21

CX LogP: -0.15

CX LogD: -1.02

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.65

Np Likeness Score: 0.70

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. Miyawaki S, Hirokami Y, Kinami K, Hoshino M, Minehira D, Miyamoto D, Nash RJ, Fleet GW, Adachi I, Toyooka N, Kato A..  (2017)  Strategy for designing selective α-l-rhamnosidase inhibitors: Synthesis and biological evaluation of l-DMDP cyclic isothioureas.,  25  (1): [PMID:27789075] [10.1016/j.bmc.2016.10.015]

Source

Source(1):

• Scientific Literature