| 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