GLUCOSE-6-PHOSPHATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H13O9P
Molecular Weight	260.1361
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	260.1361
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 8504
Sarcoplasmic/endoplasmic reticulum calcium ATP-ase 1 Target ID: CHEMBL4693 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8896749	Inhibitor 8504
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 2596

PubMed

Title	Date	PubMed
Reaction of rabbit skeletal myosin with D-glucose 6-phosphate.	1996-10	8896749
[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].	1967-11	4296886
Cofactor induced synthesis of D-glucose-6-phosphate: NADP oxidoreductase in the uterus.	1967-10	4382819
Metabolism of D-mannose in Aerobacter aerogenes: evidence for a cyclic pathway.	1966-12	4289357
Rapid screening for D-glucose-6-phosphate: NADP oxidoreductase deficiency with methylene blue.	1966-07	5945624
Purification and properties of d-glucose-6-phosphate dehydrogenase.	1955-09	13252007
Factors influencing the formation of Robison ester.	1939-08	16747027
Some factors influencing the formation of Robison ester from glycogen and inorganic phosphate in muscle extract.	1939-07	16747015
Hexosemonophosphoric esters.	1931	16744583

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 `Mon Mar 31 22:08:41 GMT 2025` Edited by `admin` on `Mon Mar 31 22:08:41 GMT 2025`
Record UNII	375AW34SQA
Record Status	`FAILED`
Record Version

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Name

Type

Language

GLUCOSE-6-PHOSPHATE

Systematic Name

English

D-GLUCOSE, 6-(DIHYDROGEN PHOSPHATE)

Preferred Name

English

GLUCOSE-6-PHOSPHATE [MI]

Common Name

English

D-GLUCOSE-6-PHOSPHATE

Systematic Name

English

ROBISON ESTER

Common Name

English

Code System Code Type Description

FDA UNII

375AW34SQA