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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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
42.2 µM [IC50]
Target ID: K(+)ATP channels (Mus musculus)
Conditions
PubMed

PubMed

TitleDatePubMed
Four new prenylated isoflavonoids in Tadehagi triquetrum.
2005 Jan 26
Antioxidant, icthyotoxicity and brine shrimp lethality tests of Magonia glabrata.
2006 Sep
Deoxygenated phosphorothioate inositol phosphate analogs: synthesis, phosphatase stability, and binding affinity.
2008 Mar 15
Patents

Sample Use Guides

Single dose of the solution of 20 g. of quebrachitol in water.
Route of Administration: Oral
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
Created
by admin
on Sat Dec 16 09:09:05 GMT 2023
Edited
by admin
on Sat Dec 16 09:09:05 GMT 2023
Record UNII
9W4JLQ7I4W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUEBRACHITOL
Common Name English
L-(-)-2-O-METHYLINOSITOL
Systematic Name English
L-QUEBRACHITOL
Common Name English
QUEBRACHIT
Common Name English
NSC-131046
Code English
BRAHOL
Common Name English
INOSITOL, 2-O-METHYL-
Systematic Name English
2-O-METHYL-L-CHIRO-INOSITOL
Systematic Name English
QUEBRACHITOL, (-)-
Common Name English
INOSITOL, 2-O-METHYL-, L-CHIRO-
Systematic Name English
NSC-26254
Code English
L-CHIRO-INOSITOL, 2-O-METHYL-
Systematic Name English
(-)-QUEBRACHITOL
Common Name English
Code System Code Type Description
WIKIPEDIA
Quebrachitol
Created by admin on Sat Dec 16 09:09:05 GMT 2023 , Edited by admin on Sat Dec 16 09:09:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID601029528
Created by admin on Sat Dec 16 09:09:05 GMT 2023 , Edited by admin on Sat Dec 16 09:09:05 GMT 2023
PRIMARY
FDA UNII
9W4JLQ7I4W
Created by admin on Sat Dec 16 09:09:05 GMT 2023 , Edited by admin on Sat Dec 16 09:09:05 GMT 2023
PRIMARY
CAS
642-38-6
Created by admin on Sat Dec 16 09:09:05 GMT 2023 , Edited by admin on Sat Dec 16 09:09:05 GMT 2023
PRIMARY
NSC
131046
Created by admin on Sat Dec 16 09:09:05 GMT 2023 , Edited by admin on Sat Dec 16 09:09:05 GMT 2023
PRIMARY
NSC
26254
Created by admin on Sat Dec 16 09:09:05 GMT 2023 , Edited by admin on Sat Dec 16 09:09:05 GMT 2023
PRIMARY