UDP-N-acetyl-α-D-muramate (PAMDB110512)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110512
Identification
Name: UDP-N-acetyl-α-D-muramate
Description:A UDP-N-acetyl-D-muramate(3−) in which the anomeric centre of the pyranose fragment has α-configuration.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • uridine diphosphate N-acetylmuramic acid
  • UDP-N-acetylmuramic acid
  • UDP-N-acetyl-D-muramate
  • UDP-MurNAc
  • UDP-N-acetylmuramoyl
Chemical Formula: C20H28N3O19P2
Average Molecular Weight: 676.4
Monoisotopic Molecular Weight: 679.1026988506
InChI Key: NQBRVZNDBBMBLJ-MQTLHLSBSA-K
InChI: InChI=1S/C20H31N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,7,9-10,12-17,19,24,27-29H,5-6H2,1-2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)/p-3/t7-,9-,10-,12-,13-,14-,15-,16-,17-,19-/m1/s1
CAS number: Not Available
IUPAC Name:uridine 5'-(3-{2-acetylamino-3-O-[(R)-1-carboxylatoethyl]-2-deoxy-α-D-glucopyranosyl} diphosphate)
Traditional IUPAC Name: 2-({2-[({[5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)propanoic acid
SMILES:CC(OC3(C(O)C(CO)OC(OP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(=O)NC(=O)2)))C(NC(C)=O)3))C(=O)[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPyrimidine nucleotides
Direct Parent Pyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • Muramic_acid
  • Pentose phosphate
  • Pentose-5-phosphate
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • N-glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Pyrimidone
  • Monoalkyl phosphate
  • Sugar acid
  • Oxane
  • Hydropyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Alkyl phosphate
  • Acetamide
  • Vinylogous amide
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Lactam
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Urea
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.6 mg/mLALOGPS
logP-1.3ALOGPS
logP-4.6ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area326.71 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity132.89 m3·mol-1ChemAxon
Polarizability58.15 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
UDP-N-acetyl-α-D-muramate + L-alanyl-γ-D-glutamyl-meso-diaminopimelate + ATP → Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + ADP + phosphate
Pathways: Not Available
Spectra
Spectra: Not Available
References
References:
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
ChEBI70757
HMDBHMDB11720
IAF126036702
KEGGC01050
PubChem24772978