ChemFOnt: Showing chemical card for N-Acetylneuraminic acid 9-phosphate (CFc000002131)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:56 UTC

Chemfont ID

CFc000002131

Molecule Identification

Common Name

N-Acetylneuraminic acid 9-phosphate

Definition

N-Acetylneuraminic acid 9-phosphate is an intermediate in the synthesis of Acetylneuraminic acid, a process occurring in the cytosolic fraction by the human enzyme N-Acetylneuraminic acid 9-phosphate (Neu5Ac 9-P) synthase, that catalyzes the synthesis of N-Acetylneuraminic acid 9-phosphate, in a reaction by the mechanism of aldol condensation of phosphoenolpyruvate (PEP) with sugar substrates, ManNAc-6-P (N-acetylmannosamine 6-phosphate) or Man-6-P (mannose 6-phosphate). N-Acetylneuraminic acid 9-phosphate is converted to N-Acetylneuraminic acid by the enzyme N-acetylneuraminate-9-phosphate phosphatase. (PMID: 16503877 , 6093772 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Acetylneuraminate 9-phosphate	ChEBI
N-Acetylneuraminic acid 9-phosphoric acid	Generator
5-(acetylamino)-3,5-Dideoxy-D-glycero-D-galacto-2-nonulosonic acid 9-(dihydrogen phosphate)	HMDB
N-Acetyl- 9-(dihydrogen phosphate)-neuraminic acid	HMDB
N-Acetyl-neuraminic acid-9-phosphate	HMDB

Chemical Formula

C₁₁H₂₀NO₁₂P

Average Molecular Weight

389.2498

Monoisotopic Molecular Weight

389.072311621

IUPAC Name

(4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-(phosphonooxy)propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid

Traditional Name

(4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-(phosphonooxy)propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid

CAS Registry Number

37992-17-9

SMILES

[H][C@]1(OC(O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)COP(O)(O)=O

InChI Identifier

InChI=1S/C11H20NO12P/c1-4(13)12-7-5(14)2-11(19,10(17)18)24-9(7)8(16)6(15)3-23-25(20,21)22/h5-9,14-16,19H,2-3H2,1H3,(H,12,13)(H,17,18)(H2,20,21,22)/t5-,6+,7+,8+,9+,11?/m0/s1

InChI Key

SQMNIXJSBCSNCI-LUWBGTNYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylneuraminate-9-phosphates. These are neuraminic acids carrying an N-acyl substituent, as well as a phosphate group at the O9-position.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acylneuraminate-9-phosphates

Alternative Parents

Substituents

N-acylneuraminate-9-phosphate
Neuraminic acid
C-glucuronide
C-glycosyl compound
Glycosyl compound
Monoalkyl phosphate
Alpha-hydroxy acid
Organic phosphoric acid derivative
Hydroxy acid
Oxane
Phosphoric acid ester
Alkyl phosphate
Pyran
Acetamide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Hemiacetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

amino sugar phosphate (CHEBI:27438 )

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0004381)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	15.9 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.7	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	223.31 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	74.65 m³·mol⁻¹	ChemAxon
Polarizability	32.62 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0004381

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023369

KNApSAcK ID

Not Available

Chemspider ID

389789

KEGG Compound ID

C06241

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440962

PDB ID

Not Available

ChEBI ID

27438

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for N-Acetylneuraminic acid 9-phosphate (CFc000002131)

MOL for CFc000002131 (N-Acetylneuraminic acid 9-phosphate)

3D MOL for CFc000002131 (N-Acetylneuraminic acid 9-phosphate)

3D SDF for CFc000002131 (N-Acetylneuraminic acid 9-phosphate)

3D-SDF for CFc000002131 (N-Acetylneuraminic acid 9-phosphate)

PDB for CFc000002131 (N-Acetylneuraminic acid 9-phosphate)

3D PDB for CFc000002131 (N-Acetylneuraminic acid 9-phosphate)

SMILES for CFc000002131 (N-Acetylneuraminic acid 9-phosphate)

INCHI for CFc000002131 (N-Acetylneuraminic acid 9-phosphate)

Structure for CFc000002131 (N-Acetylneuraminic acid 9-phosphate)

3D Structure for CFc000002131 (N-Acetylneuraminic acid 9-phosphate)