Showing metabocard for Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate (BMDB0012307)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:35:50 UTC
Update Date2020-04-22 15:49:34 UTC
BMDB IDBMDB0012307
Secondary Accession Numbers
  • BMDB12307
Metabolite Identification
Common NameUndecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate
DescriptionUndecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it. Based on a literature review a small amount of articles have been published on Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronic acid-4-acetamido-4,6-dideoxy-D-galactose pyrophosphoric acidGenerator
C55-PP-GlcNAc-mannaca-fuc4nacHMDB
Lipid IIIHMDB
ManNAcA-glcnac-fuc4nac-PP-lipidHMDB
ManNAcA-glcnac-fuc4nac-pyrophosphorylundecaprenolHMDB
Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactoseHMDB
Ceramide nonasaccharideMeSH, HMDB
Chemical FormulaC79H129N3O22P2
Average Molecular Weight1534.824
Monoisotopic Molecular Weight1533.854295851
IUPAC Name(2S,3S,4R,5S,6R)-5-acetamido-3-{[(2R,3R,4S,6R)-5-acetamido-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4-hydroxy-6-{[hydroxy({[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4R,5S,6R)-5-acetamido-3-{[(2R,3R,4S,6R)-5-acetamido-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4-hydroxy-6-{[hydroxy({hydroxy[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxyphosphoryl}oxy)phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@H](NC(C)=O)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[C@H]2O[C@H](C)C(NC(C)=O)[C@H](O)[C@H]2O)[C@H](O)[C@@H]1NC(=O)C
InChI Identifier
InChI=1S/C79H129N3O22P2/c1-50(2)27-17-28-51(3)29-18-30-52(4)31-19-32-53(5)33-20-34-54(6)35-21-36-55(7)37-22-38-56(8)39-23-40-57(9)41-24-42-58(10)43-25-44-59(11)45-26-46-60(12)47-48-97-105(93,94)104-106(95,96)103-78-68(82-64(16)86)70(88)73(65(49-83)99-78)100-77-67(81-63(15)85)71(89)74(75(102-77)76(91)92)101-79-72(90)69(87)66(61(13)98-79)80-62(14)84/h27,29,31,33,35,37,39,41,43,45,47,61,65-75,77-79,83,87-90H,17-26,28,30,32,34,36,38,40,42,44,46,48-49H2,1-16H3,(H,80,84)(H,81,85)(H,82,86)(H,91,92)(H,93,94)(H,95,96)/b51-29+,52-31+,53-33+,54-35+,55-37+,56-39+,57-41+,58-43+,59-45+,60-47+/t61-,65-,66?,67+,68-,69+,70-,71-,72-,73-,74+,75+,77-,78-,79-/m1/s1
InChI KeyPSONHUYFSWYIME-JNYPHZTQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentPolyprenyl phospho carbohydrates
Alternative Parents
Substituents
  • Polyterpenoid
  • Bactoprenol diphosphate
  • Polyprenyl phospho carbohydrate
  • Oligosaccharide phosphate
  • Polyprenyl monophosphate
  • Oligosaccharide
  • Polyprenyl phosphate skeleton
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • O-glycosyl compound
  • Isoprenoid phosphate
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyran
  • Acetamide
  • Secondary alcohol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Acetal
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.83ALOGPS
logP11.82ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area374.19 ŲChemAxon
Rotatable Bond Count46ChemAxon
Refractivity415.75 m³·mol⁻¹ChemAxon
Polarizability172.9 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0107651901-5d2fb76a53e28c193c83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0101120900-d5a528f78dbfbd08a4e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0103220900-6240dba6699d3dfac8ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004l-0642910002-2e026fe8d49f2e0d8162View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-6855550709-3673ba5ef837620eac65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4910200003-281a64f8616d394629beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0001090000-16fd8ce670774d49e820View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1193340000-9dbd03d5d4fc6fcffd74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4912050002-b947a659c9bd694b4e0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053r-4000966103-ea9764d80655086db1a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3011964025-62a8e1cdbf10f9e88626View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0032-9212745800-09948d172da1ec184f3dView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0012307
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028930
KNApSAcK IDNot Available
Chemspider ID35032433
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481400
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available