UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine (PAMDB001047)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001047
Identification
Name: UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine
Description:UDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine is a member of the chemical class known as Sulfanylbenzoic Acid Derivatives. These are benzoic acid derivatives which bear a sulfanyl group (R-SH) attached to the benzene ring.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • UDP-2,3-Bis(3-hydroxymyristoyl)glucosamine
  • UDP-2,3-Bis(3-hydroxytetradecanoyl)-D-glucosamine
  • UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine
  • UDP-2,3-Bis(b-hydroxymyristoyl)-D-glucosamine
  • UDP-2,3-Bis(beta-hydroxymyristoyl)-D-glucosamine
  • UDP-2,3-Bis(β-hydroxymyristoyl)-D-glucosamine
  • UDP-2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosamine
  • UDP-2,3-Bis[(3r)-3-hydroxymyristoyl]-α-D-glucosamine
  • UDP-2,3-Bis[(3R)-3-hydroxymyristoyl]-a-D-glucosamine
  • UDP-2,3-Bis[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine
  • UDP-2,3-Bis[(3R)-3-hydroxymyristoyl]-α-D-glucosamine
  • UDP-2,3-Diacyl-glucosamine
  • UDP-BHMyrGlc
Chemical Formula: C43H77N3O20P2
Average Molecular Weight: 1018.0271
Monoisotopic Molecular Weight: 1017.457564943
InChI Key: KOJCFMYSTWNMQW-RUAJDYCTSA-N
InChI:InChI=1S/C43H77N3O20P2/c1-3-5-7-9-11-13-15-17-19-21-29(48)25-34(51)44-36-40(64-35(52)26-30(49)22-20-18-16-14-12-10-8-6-4-2)38(54)31(27-47)63-42(36)65-68(59,60)66-67(57,58)61-28-32-37(53)39(55)41(62-32)46-24-23-33(50)45-43(46)56/h23-24,29-32,36-42,47-49,53-55H,3-22,25-28H2,1-2H3,(H,44,51)(H,57,58)(H,59,60)(H,45,50,56)/t29-,30-,31-,32-,36-,37-,38-,39-,40-,41-,42-/m1/s1
CAS number: Not Available
IUPAC Name:(3R)-N-[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]-3-hydroxytetradecanimidic acid
Traditional IUPAC Name: (3R)-N-[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]-3-hydroxytetradecanimidic acid
SMILES:[H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(O)C[C@]([H])(O)CCCCCCCCCCC
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Pyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct Parent Pyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • Saccharolipid
  • N-acyl-alpha-hexosamine
  • Glucosamine
  • Amino sugar
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Amino saccharide
  • Pyrimidone
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydroxy acid
  • Hydropyrimidine
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.204 mg/mLALOGPS
logP2.93ALOGPS
logP5.06ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area353.92 Å2ChemAxon
Rotatable Bond Count36ChemAxon
Refractivity241.06 m3·mol-1ChemAxon
Polarizability105.99 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
(R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] + UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine > acyl carrier protein + Hydrogen ion + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine
2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine <> Hydrogen ion + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Uridine 5'-diphosphate
Water + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine <>2 Hydrogen ion + 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + Uridine 5'-monophosphate
UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + Water <> Uridine 5'-monophosphate + 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + Acyl-carrier protein + (3R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] <> UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine + (3R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] + Acyl-carrier protein
UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate <> Uridine 5'-diphosphate + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate
UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate > Uridine 5'-diphosphate + 2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2910000101-46860ca31ec971b6dd89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2910001100-53f313794898ec8fecedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3910000100-1158711cf21b4e95e971View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9822230205-2ea21d2ff53d2b4aa05bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vp-8912030614-d3d1eb5aea19bc3f5320View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5912100000-acba712642beaf0be36eView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID17787
HMDB IDNot Available
Pubchem Compound ID2372447
Kegg IDC04652
ChemSpider ID1772247
Wikipedia IDNot Available
BioCyc IDOH-MYRISTOYL
EcoCyc IDOH-MYRISTOYL
Ligand ExpoUDG