Common Name |
N-Acetyl-9-O-lactoylneuraminic acid
Description |
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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms |
Value |
Source |
5-(acetylamino)-3,5-Dideoxy-9-(2-hydroxypropanoateHMDB
5-(acetylamino)-3,5-Dideoxy-9-(2-hydroxypropanoate) D-glycero-D-galacto-2-nonliosonateHMDB
5-(acetylamino)-3,5-Dideoxy-9-(2-hydroxypropanoate) D-glycero-D-galacto-2-nonliosonic acidHMDB
5-(acetylamino)-3,5-Dideoxy-9-(2-hydroxypropanoic acidHMDB
9-O-Lactoyl-N-acetylneuraminic acidHMDB
N-Acetyl-9-O-lactoylneuraminateHMDB
Neu5,8ac29HMDB
Neu5ac9LTMeSH
Chemical Formlia |
C14H23NO11
Average Molecliar Weight |
381.3325
Monoisotopic Molecliar 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 |
This compound belongs to the class of chemical entities known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.
Kingdom |
Chemical entities
Super Class |
Organic compounds
Class |
Organic oxygen compounds
Sub Class |
Organooxygen compounds
Direct Parent |
N-acylneuraminic acids
Alternative Parents |
Neuraminic acids
C-glucuronides
C-glycosyl compounds
Pyrans
Oxanes
Alpha hydroxy acids and derivatives
Dicarboxylic acids and derivatives
Acetamides
Secondary carboxylic acid amides
Secondary alcohols
Hemiacetals
Carboxylic acid esters
Oxacyclic compounds
Carboxylic acids
Carbonyl compounds
Hydrocarbon derivatives
Organic oxides
Organonitrogen compounds
Organopnictogen compounds
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
Molecliar Framework |
Aliphatic heteromonocyclic compounds
External Descriptors |
Not Available
Ontology |
Status |
Expected but not Quantified
Origin |
Endogenous
Biofunction |
Not Available
Application |
Not Available
Cellliar locations |
Cytoplasm (predicted from logP)
Physical Properties |
State |
Solid
Experimental Properties |
Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties |
Property |
Value |
Source |
Water Solubility77.3 mg/mLALOGPS
logP-2.4ALOGPS
logP-3.4ChemAxon
logS-0.69ALOGPS
pKa (Strongest Acidic)2.84ChemAxon
pKa (Strongest Basic)-0.38ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.08 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity79.13 m3·mol-1ChemAxon
Polarizability34.59 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
Spectra |
Spectra |
Not Available
Biological Properties |
Cellliar Locations |
Cytoplasm (predicted from logP)
Biofluid Locations |
Not Available
Tissue Location |
Liver
Pathways |
Not Available
Normal Concentrations |
Not Available |
Abnormal Concentrations |
|
Not Available
Associated Disorders and Diseases |
Disease References |
None
Associated OMIM IDs |
None
External Links |
DrugBank ID |
Not Available
DrugBank Metabolite ID |
Not Available
Phenol Explorer Compound ID |
Not Available
Phenol Explorer Metabolite ID |
Not Available
FoodDB 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
NuGOwiki Link |
HMDB00768
Metagene Link |
HMDB00768
METLIN ID |
5735
PubChem Compound |
192236
PDB ID |
Not Available
ChEBI ID |
Not Available
Product: Ruboxistaurin (hydrochloride)
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. |
Material Safety Data Sheet (MSDS) |
Not Available |
General References |
- Thompson JA, Miles BS, Fennessey PV: Urinary organic acids quantitated by age groups in a healthy pediatric population. Clin Chem. 1977 Sep;23(9):1734-8. [PubMed:890917 ]
- Kleineidam RG, Hofmann O, Reuter G, Schauer R: Indications for the enzymatic synthesis of 9-O-lactoyl-N-acetylneuraminic acid in equine liver. Glycoconj J. 1993 Feb;10(1):116-9. [PubMed:8358222 ]
|
PMID: 15277314