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Showing metabocard for N-Acetyl-D-glucosaminyldiphosphodolichol (HMDB0001445)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:30:25 UTC
HMDB IDHMDB0001445
Secondary Accession Numbers
  • HMDB01445
Metabolite Identification
Common NameN-Acetyl-D-glucosaminyldiphosphodolichol
DescriptionThis compound is an intermediate in N-glycan biosynthesis, and the byproduct of N-acetylglucosaminyldiphosphodolichol (EC 2.4.1.141) and UDP-N-acetylglucosamine-dolichyl-phosphate (EC 2.7.8.15). (KEGG) This compound and its corresponding enzymes are implicated in the developmental programmes of a variety of eukaryotes. (PMID: 10024536 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-Acetyl-D-glucosaminyl-diphosphodolicholHMDB
Chemical FormulaC23H43NO12P2
Average Molecular Weight587.5345
Monoisotopic Molecular Weight587.226048869
IUPAC Name{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}({[hydroxy({[(6E)-3,7,11-trimethyldodeca-6,10-dien-1-yl]oxy})phosphoryl]oxy})phosphinic acid
Traditional Name[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy({hydroxy[(6E)-3,7,11-trimethyldodeca-6,10-dien-1-yl]oxyphosphoryl}oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](OP(O)(=O)OP(O)(=O)OCCC(C)CC\C=C(/C)CCC=C(C)C)[C@H](NC(=O)C)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C23H43NO12P2/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-33-37(29,30)36-38(31,32)35-23-20(24-18(5)26)22(28)21(27)19(14-25)34-23/h8,10,17,19-23,25,27-28H,6-7,9,11-14H2,1-5H3,(H,24,26)(H,29,30)(H,31,32)/b16-10+/t17?,19-,20-,21-,22-,23+/m1/s1
InChI KeyOZGJPDIBINDRGZ-GKXPKBPWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acyl-alpha-hexosamines
Alternative Parents
Substituents
  • N-acyl-alpha-hexosamine
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • Hexose monosaccharide
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Primary alcohol
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1 g/LALOGPS
logP1.3ALOGPS
logP1.54ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)1.75ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area201.31 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity139.28 m³·mol⁻¹ChemAxon
Polarizability58.82 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ai-7809080000-1d59a7a76b20f6c81771View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0036-8829346000-b21da2099e1622d707d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0193080000-9443ac239db9306981beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2291000000-d8e47b745e7577d5f718View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4960230000-74dd39082e1fcbef4933View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-9316230000-0f0ed3fc6a3e0966260dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fu-9617010000-0caba05e81e7f8d9c4c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-5910000000-0ddc418e7fce8b99a44eView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022628
KNApSAcK IDNot Available
Chemspider ID10128137
KEGG Compound IDC04500
BioCyc IDNot Available
BiGG ID1809448
Wikipedia LinkNot Available
METLIN ID6251
PubChem Compound11953837
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Meissner JD, Naumann A, Mueller WH, Scheibe RJ: Regulation of UDP-N-acetylglucosamine:dolichyl-phosphate N-acetylglucosamine-1-phosphate transferase by retinoic acid in P19 cells. Biochem J. 1999 Mar 1;338 ( Pt 2):561-8. [PubMed:10024536 ]

Enzymes

Enzyme Details
1. UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferase
General function:
Involved in phospho-N-acetylmuramoyl-pentapeptide-transferase activity
Specific function:
Catalyzes the initial step in the synthesis of dolichol-P-P-oligosaccharides.
Gene Name:
DPAGT1
Uniprot ID:
Q9H3H5
Molecular weight:
46089.485
Enzyme Details
2. UDP-N-acetylglucosamine transferase subunit ALG13 homolog
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Isoform 2 may be involved in protein N-glycosylation, second step of the dolichol-linked oligosaccharide pathway.
Gene Name:
ALG13
Uniprot ID:
Q9NP73
Molecular weight:
15149.285