alpha-D-glucose 1-phosphate

HCID 65533CAS 59-56-3

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Basic information

Standard SMILES: O=P(O)(O)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChIKey: HXXFSFRBOHSIMQ-VFUOTHLCSA-N
Molecular formula: C6H13O9P
Average molar mass: 260.14 g/mol
Monoisotopic mass: 260.02971863

Overview

Alpha-D-glucose 1-phosphate is a D-glucopyranose 1-phosphate in which the anomeric centre has alpha-configuration. It is functionally related to an alpha-D-glucose. It is a conjugate acid of an alpha-D-glucose 1-phosphate(2-).

Names & identifiers

Preferred name: alpha-D-glucose 1-phosphate
IUPAC: [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen phosphate
English name: glucose 1-(dihydrogen phosphate)
Molecular formula: C6H13O9P
Molecular weight: 260.13

Names & synonyms

alpha-D-glucose-1-phosphatealpha-D-Glucose 1-phosphatealpha-D-Glucopyranosyl phosphate1-O-phosphono-alpha-D-glucopyranosealpha-D-Glucopyranose, 1-(dihydrogen phosphate)CHEBI:29042DTXSID90889321.alpha.-D-Glucopyranose, 1-(dihydrogen phosphate)alpha-D-glucopyranose 1-(dihydrogen phosphate)[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen phosphate((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl) dihydrogen phosphateRefChem:555626

Show more names

GLC-1-Pglucose-1Palpha-D-glucose-1-Pa-Glucose-1-phosphateGlucose monophosphate.α-D-glucose1-phosphateD-glucose-alpha-1-phosphateHXXFSFRBOHSIMQ-VFUOTHLCSA-N

DTXCID001028584Glucose-1-phosphatecori ester59-56-3Glucose 1-(dihydrogen phosphate)alpha-glucose-1-phosphateGlucose monophosphateD-glucose 1-phosphate

Database identifiers

CAS: 59-56-3
PubChem CID: 65533
DTXSID: DTXSID90889321
ChEBI: CHEBI:29042
UNII: CIX3U01VAU
EC Number: 200-435-8
Nikkaji: J40.065C

Properties

Computed structural properties

XLogP: -3.8
Topological polar surface area: 157 Å²
Hydrogen bond donors: 6
Hydrogen bond acceptors: 9
Rotatable bonds: 3
Heavy atoms: 16
Formal charge: 0
Complexity: 277

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Solubility1000.0 mg/mL

Physical DescriptionSolid

Dissociation Constants1.11

Collision Cross Section · 3 items

161.83 Å² [M+Na]+ [CCS Type: DT; Method: stepped-field]

145.48 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

149.4 Å² [M-H]-

Physicochemical properties

Boiling point: 603 · 603.0±65.0 °C(Predicted)
Density: 1.9 · 1.90±0.1 g/cm3(Predicted)
solubility: Soluble (water), slightly soluble (ethanol)
form: Solid
pka: 6.504 · pKa: 6.504(25°C)
color: White to off-white
optical activity: 120 · Alpha type +120
Cosmetics Ingredients Functions: SKIN CONDITIONING - EMOLLIENT
FDA UNII: 3 U01VAU · CIX3U01VAU
EPA Substance Registry System: 1 · .alpha.-D-Glucopyranose, 1-(dihydrogen phosphate) (59-56-3)
RIDADR: 1759 · 1759
TSCA: TSCA listed
HazardClass: 8 · 8
PackingGroup: III

Safety & regulation

Safety data

tsca: TSCA listed
ridadr: 1759
hazard_class: 8
packing_group: III

Chemistry & industry

Pharmacology

Tissue LocationsFibroblasts

Cellular LocationsCytoplasm

Metabolite PathwaysCongenital disorder of glycosylation CDG-IId

Uses & manufacturing

General Manufacturing Information.alpha.-D-Glucopyranose, 1-(dihydrogen phosphate): INACTIVE

Applications

Usesα-D-Glucose-1-phosphate is an important intermediate in sugar metabolism, functioning as a glycosyl donor in glycosyl transfer reactions and participating in glycogen synthesis and degradation through the action of phosphorylases[1].