U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C7H14O6
Molecular Weight 194.1825
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUEBRACHITOL

SMILES

CO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O

InChI

InChIKey=DSCFFEYYQKSRSV-FIZWYUIZSA-N
InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5+,6+,7-/m0/s1

HIDE SMILES / InChI

Molecular Formula C7H14O6
Molecular Weight 194.1825
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Quebrachitol (QCT), a bioactive plant constituent, is a naturally occurring optically active cyclitols. QCT could serve as the starting material of inositol or its derivatives to participate in several important pathways and may act as a potential anticancer or antidiabetic drug lead to arrest or reverse these diseases. According to the literature reported before, QCT exerted its biological functions, by involving IP3 receptor, b-glucosidase, PAFR, COX2, nitric oxide synthase, and K(+)ATP channels. Quebrachitol reduces the gastric damage induced by ethanol and indomethacin. The potential of quebrachitol as a sugar substitute for diabetics has been investigated. Even though the early study reported that this methylcyclitol seems neither to prevent hypoglycemia nor to raise blood sugar content, another work showed that quebrachitol has hypoglycemic effects in hyperglycemic rats. Unfortunately, all three persons who took quebrachitol by mouth had fairly severe diarrhea.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
42.2 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Single dose of the solution of 20 g. of quebrachitol in water.
Route of Administration: Oral
In Vitro Use Guide
Fluorescence microscopy using acridine orange/ethidium bromide double staining affirmed the absence of 6-hydroxydopamine (200 uM)-induced morphological changes characteristic of apoptosis/necrosis in cultures of rat fetal mesencephalic cells, pretreated with quebrachitol (100 ug/ml).
Substance Class Chemical
Record UNII
9W4JLQ7I4W
Record Status Validated (UNII)
Record Version