ChemFOnt: Showing chemical card for guanosine 5'-diphospho-fucose (CFc000042966)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:46 UTC

Chemfont ID

CFc000042966

Molecule Identification

Common Name

guanosine 5'-diphospho-fucose

Definition

guanosine 5'-diphospho-fucose, also known as GDP-beta-L-Fucose or Fucose, GDP, is classified as a member of the Purine nucleotide sugars. Purine nucleotide sugars are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. guanosine 5'-diphospho-fucose is considered to be slightly soluble (in water) and acidic

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
GDP-beta-L-Fucose	Kegg
GDP-b-L-Fucose	Generator
GDP-Β-L-fucose	Generator
Diphosphate fucose, guanosine	HMDB
Diphosphofucose, guanosine	HMDB
Fucose, GDP	HMDB
Fucose, guanosine diphosphate	HMDB
GDP Fucose	HMDB
Guanosine diphosphate fucose	HMDB
Guanosine diphosphofucose	HMDB

Chemical Formula

C₁₆H₂₅N₅O₁₅P₂

Average Molecular Weight

589.344

Monoisotopic Molecular Weight

589.082239121

IUPAC Name

{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}({[hydroxy({[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid

Traditional Name

[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)oxolan-2-yl]methoxy([hydroxy([(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]oxy)phosphinic acid

CAS Registry Number

15839-70-0

SMILES

[H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])O[C@@]([H])(C)[C@@]([H])(O)[C@@]([H])(O)[C@]2([H])O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5+,7+,8+,9+,10+,11-,14+,15+/m0/s1

InChI Key

LQEBEXMHBLQMDB-JGQUBWHWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine nucleotide sugars

Direct Parent

Purine nucleotide sugars

Alternative Parents

Substituents

Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-oxopurine
Hypoxanthine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Pyrimidone
Pyrimidine
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Tetrahydrofuran
Vinylogous amide
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Azacycle
Polyol
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organopnictogen compound
Alcohol
Primary amine
Organonitrogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

GDP-L-fucose (CHEBI:13332 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062554)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	7.02 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-4.7	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.71	ChemAxon
pKa (Strongest Basic)	3.38	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	308.19 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	127.55 m³·mol⁻¹	ChemAxon
Polarizability	50.04 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0062554

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00007245

Chemspider ID

Not Available

KEGG Compound ID

C00325

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10918995

PDB ID

Not Available

ChEBI ID

13332

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for guanosine 5'-diphospho-fucose (CFc000042966)

MOL for CFc000042966 (guanosine 5'-diphospho-fucose)

3D MOL for CFc000042966 (guanosine 5'-diphospho-fucose)

3D SDF for CFc000042966 (guanosine 5'-diphospho-fucose)

3D-SDF for CFc000042966 (guanosine 5'-diphospho-fucose)

PDB for CFc000042966 (guanosine 5'-diphospho-fucose)

3D PDB for CFc000042966 (guanosine 5'-diphospho-fucose)

SMILES for CFc000042966 (guanosine 5'-diphospho-fucose)

INCHI for CFc000042966 (guanosine 5'-diphospho-fucose)

Structure for CFc000042966 (guanosine 5'-diphospho-fucose)

3D Structure for CFc000042966 (guanosine 5'-diphospho-fucose)