Showing metabocard for Lacto-N-biose I (BMDB0006575)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:23:32 UTC
Update Date2020-04-22 15:17:55 UTC
BMDB IDBMDB0006575
Secondary Accession Numbers
  • BMDB06575
Metabolite Identification
Common NameLacto-N-biose I
DescriptionLacto-N-biose I, also known as gal(b1-3)a-glcnac, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. Based on a literature review a significant number of articles have been published on Lacto-N-biose I.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Gal(b1-3)a-glcnacChEBI
WURCS=2.0/2,2,1/[a2122h-1a_1-5_2*ncc/3=o][a2112h-1b_1-5]/1-2/a3-b1ChEBI
Gal-1,3-glcnacMeSH
Galactosyl-1,3-N-acetylglucosamineMeSH
2-acetamido-2-Deoxy-3-O-b-D-galactopyranosyl-D-glucoseHMDB
2-acetamido-2-Deoxy-3-O-beta-D-galactopyranosyl-D-glucopyranoseHMDB
2-acetamido-2-Deoxy-3-O-beta-D-galactopyranosyl-D-glucoseHMDB
2-acetamido-2-Deoxy-3-O-beta-delta-galactopyranosyl-delta-glucopyranoseHMDB
2-acetamido-2-Deoxy-3-O-beta-delta-galactopyranosyl-delta-glucoseHMDB
beta-D-Gal-(1->3)-D-glcnacHMDB
beta-D-Galactopyranosyl-(1->3)-N-acetyl-D-glucosamineHMDB
beta-delta-Gal-(1->3)-delta-glcnacHMDB
beta-delta-Galactopyranosyl-(1->3)-N-acetyl-delta-glucosamineHMDB
Gal(beta1-3)glcnacHMDB
lacto-N-BioseHMDB
O-beta-D-Galactopyranosyl-(1->3)-N-acetylglucosamineHMDB
O-beta-delta-Galactopyranosyl-(1->3)-N-acetylglucosamineHMDB
N-[(2S,3R,4R,5S,6R)-2,5-Dihydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]ethanimidateGenerator, HMDB
Lacto-N-biose IMeSH
Chemical FormulaC14H25NO11
Average Molecular Weight383.3484
Monoisotopic Molecular Weight383.142760647
IUPAC NameN-[(2S,3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
Traditional NameN-[(2S,3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
CAS Registry Number50787-09-2
SMILES
CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C14H25NO11/c1-4(18)15-7-12(9(20)6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8+,9-,10+,11-,12-,13+,14+/m1/s1
InChI KeyHMQPEDMEOBLSQB-RCBHQUQDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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-2.8ALOGPS
logP-5ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)11.49ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area198.4 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.44 m³·mol⁻¹ChemAxon
Polarizability35.9 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006575
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023977
KNApSAcK IDNot Available
Chemspider ID4450965
KEGG Compound IDC06372
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5288905
PDB IDNot Available
ChEBI ID145593
References
Synthesis ReferenceJain R K; Locke R D; Matta K L A convenient synthesis of lacto-N-biose I [beta-D-Gal p-(1-->3)-beta-D- Glc pNAc] linked oligosaccharides from phenyl O-(tetra-O-acetyl-beta-D- galactopyranosyl)-(1-->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio- beta-D- glucopyranoside. Carbohydrate research (1993), 241 165-76.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available