Showing metabocard for Glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol (BMDB0012232)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:34:38 UTC
Update Date2020-04-22 15:49:11 UTC
BMDB IDBMDB0012232
Secondary Accession Numbers
  • BMDB12232
Metabolite Identification
Common NameGlucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol
DescriptionGlucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a small amount of articles have been published on Glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol.
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC156H260N2O67P2
Average Molecular Weight3297.6543
Monoisotopic Molecular Weight3295.647459028
IUPAC Name{[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-5-{[(2S,3S,4S,5R,6R)-6-({[(2S,3S,4S,5R,6R)-4-{[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-({[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,5-dihydroxyoxan-2-yl]oxy}methyl)-4-{[(2R,3S,4S,5S,6R)-3-{[(2R,3S,4S,5S,6R)-3-{[(2R,3S,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}[({[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pentadecaen-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
Traditional Name[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-5-{[(2S,3S,4S,5R,6R)-6-({[(2S,3S,4S,5R,6R)-4-{[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-({[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,5-dihydroxyoxan-2-yl]oxy}methyl)-4-{[(2R,3S,4S,5S,6R)-3-{[(2R,3S,4S,5S,6R)-3-{[(2R,3S,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy({[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pentadecaen-1-yl]oxy(hydroxy)phosphoryl}oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@H](OC[C@H]2O[C@H](OC[C@H]3O[C@@H](O[C@H]4[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]4CO)O[C@H]4[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]4CO)OP(=O)(O)OP(=O)(O)OCCC(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)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](O)[C@@H](O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@@H]4O)[C@@H]3O)[C@@H](O)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H]2O)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C156H260N2O67P2/c1-79(2)35-20-36-80(3)37-21-38-81(4)39-22-40-82(5)41-23-42-83(6)43-24-44-84(7)45-25-46-85(8)47-26-48-86(9)49-27-50-87(10)51-28-52-88(11)53-29-54-89(12)55-30-56-90(13)57-31-58-91(14)59-32-60-92(15)61-33-62-93(16)63-34-64-94(17)65-66-202-226(196,197)225-227(198,199)224-146-110(158-96(19)170)122(182)136(106(76-168)212-146)215-145-109(157-95(18)169)121(181)137(105(75-167)211-145)216-152-135(195)140(219-155-144(129(189)117(177)102(72-164)209-155)223-156-143(128(188)116(176)103(73-165)210-156)222-151-134(194)138(118(178)104(74-166)206-151)217-148-130(190)123(183)111(171)97(67-159)203-148)120(180)108(214-152)77-200-147-133(193)139(218-154-142(127(187)115(175)101(71-163)208-154)221-150-132(192)125(185)113(173)99(69-161)205-150)119(179)107(213-147)78-201-153-141(126(186)114(174)100(70-162)207-153)220-149-131(191)124(184)112(172)98(68-160)204-149/h35,37,39,41,43,45,47,49,51,53,55,57,59,61,63,94,97-156,159-168,171-195H,20-34,36,38,40,42,44,46,48,50,52,54,56,58,60,62,64-78H2,1-19H3,(H,157,169)(H,158,170)(H,196,197)(H,198,199)/b80-37+,81-39+,82-41+,83-43+,84-45+,85-47+,86-49+,87-51+,88-53+,89-55+,90-57+,91-59+,92-61+,93-63+/t94?,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123+,124+,125+,126+,127+,128+,129+,130-,131+,132+,133+,134+,135+,136-,137-,138+,139+,140+,141+,142+,143+,144+,145+,146+,147+,148-,149-,150-,151-,152+,153+,154-,155-,156-/m1/s1
InChI KeyMLMXJWWXMCLAMG-FTSRHZIGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamine and derivatives
Alternative Parents
Substituents
  • Glutamine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Fatty amide
  • N-acyl-amine
  • Fatty acid
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
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
logP3.26ALOGPS
logP3.35ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count64ChemAxon
Hydrogen Donor Count39ChemAxon
Polar Surface Area1080.83 ŲChemAxon
Rotatable Bond Count89ChemAxon
Refractivity816.36 m³·mol⁻¹ChemAxon
Polarizability353.94 ųChemAxon
Number of Rings12ChemAxon
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, Positivesplash10-004i-2390205124-3ff3ebb1303cdc22af07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05dl-7460509156-f54a690fc1a37593278fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aed-3441409055-7bb12aa06acd2c6a2395View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01rb-0291150814-75a574f872aa06aeb781View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0591011012-412b23c45fc1837363c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1891000000-a1ff7655b6017b4aa732View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004s-0290000000-35b310334e7df430274eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-1590214115-e6e7aaa86a1946b89492View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-2490313133-910d4dfae831d7e4770aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0390000000-1f5e4f40d945c9e8b8a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0390000001-2c72aeae14fcc8244f88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3980233000-362dccd249bb5c7d9ec0View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0012232
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028875
KNApSAcK IDNot Available
Chemspider ID35032422
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481393
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available