ChemFOnt: Showing chemical card for N-Acetyl-9-O-lactoylneuraminic acid (CFc000000614)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:03 UTC

Chemfont ID

CFc000000614

Molecule Identification

Common Name

N-Acetyl-9-O-lactoylneuraminic acid

Definition

N-Acetyl-9-O-lactoylneuraminic acid is a sialic acid produced by sialate 9-O-lactoyltransferases. Lactoylation of CMP-N-acetylneuraminic acid, N-acetylneuramimic acid and glycoconjugate-bound N-acetylneuramimic acid has been observed, with the glycoconjugate form being the best substrate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Acetyl-9-O-lactoylneuraminate	Generator
5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoate	HMDB
5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoate) D-glycero-D-galacto-2-nonulosonate	HMDB
5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoate) D-glycero-D-galacto-2-nonulosonic acid	HMDB
5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoic acid	HMDB
9-O-Lactoyl-N-acetylneuraminic acid	HMDB
Neu5,8ac29	HMDB
Neu5ac9LT	HMDB
(2S,4S,5R,6R)-6-[(1R,2R)-1,2-Dihydroxy-3-[(2-hydroxypropanoyl)oxy]propyl]-2,4-dihydroxy-5-[(1-hydroxyethylidene)amino]oxane-2-carboxylate	HMDB
N-Acetyl-9-O-lactoylneuraminic acid	MeSH

Chemical Formula

C₁₄H₂₃NO₁₁

Average Molecular Weight

381.3325

Monoisotopic Molecular Weight

381.127110583

IUPAC Name

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

Traditional Name

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

CAS Registry Number

92935-30-3

SMILES

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

InChI Identifier

InChI=1S/C14H23NO11/c1-5(16)12(21)25-4-8(19)10(20)11-9(15-6(2)17)7(18)3-14(24,26-11)13(22)23/h5,7-11,16,18-20,24H,3-4H2,1-2H3,(H,15,17)(H,22,23)/t5?,7-,8+,9+,10+,11+,14-/m0/s1

InChI Key

XXNWSGSWDRDYLR-NVZZXFSUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acylneuraminic acids

Alternative Parents

Substituents

N-acylneuraminic acid
Neuraminic acid
C-glucuronide
C-glycosyl compound
Glycosyl compound
Alpha-hydroxy acid
Dicarboxylic acid or derivatives
Pyran
Oxane
Hydroxy acid
Acetamide
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Secondary alcohol
Hemiacetal
Carboxylic acid derivative
Oxacycle
Carboxylic acid
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Liver (HMDB: HMDB0000768)

Cellular substructure

Cytoplasm (HMDB: HMDB0000768)

Source

Endogenous

Endogenous (HMDB: HMDB0000768)

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	77.3 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-3.4	ChemAxon
logS	-0.69	ALOGPS
pKa (Strongest Acidic)	2.84	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.08 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	79.13 m³·mol⁻¹	ChemAxon
Polarizability	34.59 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

HMDB0000768

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022232

KNApSAcK ID

Not Available

Chemspider ID

166877

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5735

PubChem Compound

192236

PDB ID

Not Available

ChEBI ID

165243

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Kleineidam, Reinhard G.; Hofmann, Olaf; Reuter, Gerd; Schauer, Roland. Indications for the enzymic synthesis of 9-O-lactoyl-N-acetylneuraminic acid in equine liver. Glycoconjugate Journal (1993), 10(1), 116-19.

Showing chemical card for N-Acetyl-9-O-lactoylneuraminic acid (CFc000000614)

MOL for CFc000000614 (N-Acetyl-9-O-lactoylneuraminic acid)

3D MOL for CFc000000614 (N-Acetyl-9-O-lactoylneuraminic acid)

3D SDF for CFc000000614 (N-Acetyl-9-O-lactoylneuraminic acid)

3D-SDF for CFc000000614 (N-Acetyl-9-O-lactoylneuraminic acid)

PDB for CFc000000614 (N-Acetyl-9-O-lactoylneuraminic acid)

3D PDB for CFc000000614 (N-Acetyl-9-O-lactoylneuraminic acid)

SMILES for CFc000000614 (N-Acetyl-9-O-lactoylneuraminic acid)

INCHI for CFc000000614 (N-Acetyl-9-O-lactoylneuraminic acid)

Structure for CFc000000614 (N-Acetyl-9-O-lactoylneuraminic acid)

3D Structure for CFc000000614 (N-Acetyl-9-O-lactoylneuraminic acid)