5-Amino-1-hydroxymethyl-cyclohexane-1,2,3,4-tetraol

ID: ALA222396

Chembl Id: CHEMBL222396

Max Phase: Preclinical

Molecular Formula: C7H15NO5

Molecular Weight: 193.20

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Valinolamine | Valiolamine

Canonical SMILES:  N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C7H15NO5/c8-3-1-7(13,2-9)6(12)5(11)4(3)10/h3-6,9-13H,1-2,8H2/t3-,4-,5+,6-,7-/m0/s1

Standard InChI Key:  VDLOJRUTNRJDJO-ZYNSJIGGSA-N

Alternative Forms

1. Parent:

   

   ALA222396

   VALIOLAMINE

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

Calculated Properties

Molecular Weight: 193.20

Molecular Weight (Monoisotopic): 193.0950

AlogP: -3.48

#Rotatable Bonds: 1

Polar Surface Area: 127.17

Molecular Species: BASE

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.46

CX Basic pKa: 8.51

CX LogP: -3.96

CX LogD: -5.10

Aromatic Rings: 0

Heavy Atoms: 13

QED Weighted: 0.26

Np Likeness Score: 2.74

References

1. Horii S, Fukase H, Matsuo T, Kameda Y, Asano N, Matsui K..  (1986)  Synthesis and alpha-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents.,  29  (6): [PMID:3519969] [10.1021/jm00156a023]

2. Kuriyama C, Kamiyama O, Ikeda K, Sanae F, Kato A, Adachi I, Imahori T, Takahata H, Okamoto T, Asano N..  (2008)  In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.,  16  (15): [PMID:18595718] [10.1016/j.bmc.2008.06.026]

3. Karade SS, Hill ML, Kiappes JL, Manne R, Aakula B, Zitzmann N, Warfield KL, Treston AM, Mariuzza RA..  (2021)  N-Substituted Valiolamine Derivatives as Potent Inhibitors of Endoplasmic Reticulum α-Glucosidases I and II with Antiviral Activity.,  64  (24.0): [PMID:34870992] [10.1021/acs.jmedchem.1c01377]

Source

Source(1):

• Scientific Literature