GLUCOSE-6-PHOSPHATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H13O9P
Molecular Weight	260.1358
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H](O)C=O

InChI

InChIKey=VFRROHXSMXFLSN-SLPGGIOYSA-N

InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h1,3-6,8-11H,2H2,(H2,12,13,14)/t3-,4+,5+,6+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C6H13O9P
Molecular Weight	260.1358
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11879177 | https://www.ncbi.nlm.nih.gov/pubmed/8896749 | https://www.ncbi.nlm.nih.gov/pubmed/16744583 | https://www.ncbi.nlm.nih.gov/books/NBK22395/

Glucose-6-phosphate belongs to the class of organic compounds known as monosaccharide phosphates. It lies at the start of two major metabolic pathways: glycolysis and the pentose phosphate pathway. It is a glucose-6-phosphatase substrate. Hexokinase is inhibited by its product, glucose 6-phosphate. The non-enzymatic glycation of myosin by glucose 6-phosphate is probably the primary cause for the observed loss of the ATPase activity of myosin.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucose-6-phosphatase 1 Target ID: CHEMBL2282 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11879177 \| https://www.ncbi.nlm.nih.gov/pubmed/8574017	Substrate 661
Brain hexokinase (guinea pig) 1 Target ID: Brain hexokinase (guinea pig) Sources: https://www.ncbi.nlm.nih.gov/pubmed/6049880 \| https://www.ncbi.nlm.nih.gov/books/NBK22395	Inhibitor 8297
Sarcoplasmic/endoplasmic reticulum calcium ATP-ase 1 Target ID: CHEMBL4693 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8896749	Inhibitor 8297
Glucose-6-phosphate isomerase 1 Target ID: P08059 Gene ID: 397602.0 Gene Symbol: GPI Target Organism: Sus scrofa (Pig) Sources: https://www.ncbi.nlm.nih.gov/pubmed/6115414	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Hexosemonophosphoric esters.	1931	16744583
Factors influencing the formation of Robison ester.	1939 Aug	16747027
Some factors influencing the formation of Robison ester from glycogen and inorganic phosphate in muscle extract.	1939 Jul	16747015
Purification and properties of d-glucose-6-phosphate dehydrogenase.	1955 Sep	13252007
Metabolism of D-mannose in Aerobacter aerogenes: evidence for a cyclic pathway.	1966 Dec	4289357
Rapid screening for D-glucose-6-phosphate: NADP oxidoreductase deficiency with methylene blue.	1966 Jul	5945624
[Studies on the biosynthesis of cyclitol, 18. On the mode of action of the enzyme from Candida utilis in converting D-glucose-6-phosphate to L-1-O-phospho-myo-inositol].	1967 Nov	4296886
Cofactor induced synthesis of D-glucose-6-phosphate: NADP oxidoreductase in the uterus.	1967 Oct	4382819
Reaction of rabbit skeletal myosin with D-glucose 6-phosphate.	1996 Oct	8896749

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Incubation of rabbit skeletal myosin with 1 to 3 mM D-glucose 6-phosphate over a period of several hours resulted in the inhibition of the K(+)- and actin activated-ATPase activities. When the myosin was incubated with 3 mM [3H] labeled glucose 6-phosphate for 28 h up to one mole of glucose 6-phosphate was incorporated per 4.7 x 10(5) g of myosin.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:31:41 UTC 2023` Edited by `admin` on `Sat Dec 16 08:31:41 UTC 2023`
Record UNII	375AW34SQA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GLUCOSE-6-PHOSPHATE

Systematic Name

English

GLUCOSE-6-PHOSPHATE [MI]

Common Name

English

D-GLUCOSE-6-PHOSPHATE

Systematic Name

English

ROBISON ESTER

Common Name

English

D-GLUCOSE, 6-(DIHYDROGEN PHOSPHATE)

Common Name

English

Code System Code Type Description

FDA UNII

375AW34SQA