Showing metabocard for N-Acetyl-9-O-lactoylneuraminic acid (BMDB0000768)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:36:19 UTC
Update Date2020-05-11 20:21:36 UTC
BMDB IDBMDB0000768
Secondary Accession Numbers
  • BMDB00768
Metabolite Identification
Common NameN-Acetyl-9-O-lactoylneuraminic acid
DescriptionN-Acetyl-9-O-lactoylneuraminic acid, also known as 9-O-lactoyl-N-acetylneuraminic acid or neu5,8ac29, belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. Based on a literature review a small amount of articles have been published on N-Acetyl-9-O-lactoylneuraminic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-Acetyl-9-O-lactoylneuraminateGenerator
5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoateHMDB
5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoate) D-glycero-D-galacto-2-nonulosonateHMDB
5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoate) D-glycero-D-galacto-2-nonulosonic acidHMDB
5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoic acidHMDB
9-O-Lactoyl-N-acetylneuraminic acidHMDB
Neu5,8ac29HMDB
Neu5ac9LTHMDB
(2S,4S,5R,6R)-6-[(1R,2R)-1,2-Dihydroxy-3-[(2-hydroxypropanoyl)oxy]propyl]-2,4-dihydroxy-5-[(1-hydroxyethylidene)amino]oxane-2-carboxylateHMDB
N-Acetyl-9-O-lactoylneuraminic acidMeSH
Chemical FormulaC14H23NO11
Average Molecular Weight381.3325
Monoisotopic Molecular Weight381.127110583
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 Number92935-30-3
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 KeyXXNWSGSWDRDYLR-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-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 FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.4ALOGPS
logP-3.4ChemAxon
logS-0.69ALOGPS
pKa (Strongest Acidic)2.84ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.08 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity79.13 m³·mol⁻¹ChemAxon
Polarizability34.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000768
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022232
KNApSAcK IDNot Available
Chemspider ID166877
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5735
PubChem Compound192236
PDB IDNot Available
ChEBI ID165243
References
Synthesis ReferenceKleineidam, 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 ReferencesNot Available