Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-02-26 10:22:29 UTC
Update Date2021-09-14 15:18:00 UTC
HMDB IDHMDB0011720
Secondary Accession Numbers
  • HMDB11720
Metabolite Identification
Common NameUDP-N-acetylmuraminate
DescriptionUDP-N-acetylmuraminate, also known as UDP-N-acetylmuraminic acid, 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. UDP-N-acetylmuraminate has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make UDP-N-acetylmuraminate a potential biomarker for the consumption of these foods. UDP-N-acetylmuraminate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on UDP-N-acetylmuraminate.
Structure
Data?1582752944
Synonyms
ValueSource
UDP-N-Acetylmuraminic acidGenerator
N-Acetylmuramoyl-UDPHMDB
UDP-MurNAcHMDB
UDP-N-Acetyl-D-muramateHMDB
UDP-N-AcetylmuramateHMDB
UDP-N-Acetylmuramic acidHMDB
Uridine diphosphate N-acetylmuramic acidHMDB
Chemical FormulaC20H31N3O19P2
Average Molecular Weight679.4164
Monoisotopic Molecular Weight679.102698849
IUPAC Name2-{[2-({[({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-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
Traditional Name2-({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
CAS Registry NumberNot Available
SMILES
CC(OC1C(O)C(CO)OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=CC(=O)NC2=O)C1NC(C)=O)C(O)=O
InChI Identifier
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)
InChI KeyNQBRVZNDBBMBLJ-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct ParentPyrimidine 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 FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility11.6 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity132.89 m³·mol⁻¹ChemAxon
Polarizability58.15 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+251.4131661259
DarkChem[M-H]-237.41131661259
DeepCCS[M+H]+211.87730932474
DeepCCS[M-H]-209.98230932474
DeepCCS[M-2H]-243.22130932474
DeepCCS[M+Na]+217.49130932474
AllCCS[M+H]+231.532859911
AllCCS[M+H-H2O]+230.832859911
AllCCS[M+NH4]+232.032859911
AllCCS[M+Na]+232.232859911
AllCCS[M-H]-232.832859911
AllCCS[M+Na-2H]-235.132859911
AllCCS[M+HCOO]-237.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
UDP-N-acetylmuraminateCC(OC1C(O)C(CO)OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=CC(=O)NC2=O)C1NC(C)=O)C(O)=O5220.3Standard polar33892256
UDP-N-acetylmuraminateCC(OC1C(O)C(CO)OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=CC(=O)NC2=O)C1NC(C)=O)C(O)=O3540.0Standard non polar33892256
UDP-N-acetylmuraminateCC(OC1C(O)C(CO)OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=CC(=O)NC2=O)C1NC(C)=O)C(O)=O5405.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w2c-5322976000-efe17d0e856af1a411b22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - UDP-N-acetylmuraminate GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - UDP-N-acetylmuraminate 10V, Positive-QTOFsplash10-03di-0900003000-8d55c9b947db81436ea72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - UDP-N-acetylmuraminate 20V, Positive-QTOFsplash10-03di-3911000000-0a57018153dc082345f92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - UDP-N-acetylmuraminate 40V, Positive-QTOFsplash10-03di-5900001000-81426c8d4b738caf58402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - UDP-N-acetylmuraminate 10V, Negative-QTOFsplash10-0np4-9454518000-cff6c0ae41e5d5c2471b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - UDP-N-acetylmuraminate 20V, Negative-QTOFsplash10-03ec-9502301000-bdeabbd99b46937b13b52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - UDP-N-acetylmuraminate 40V, Negative-QTOFsplash10-06r6-6913000000-780647edc29ebc46ff4f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - UDP-N-acetylmuraminate 10V, Positive-QTOFsplash10-0ue9-0000096000-98b30cf20b9cd158b3ae2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - UDP-N-acetylmuraminate 20V, Positive-QTOFsplash10-0gx3-0100197000-4fce391b3932c157d9322021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - UDP-N-acetylmuraminate 40V, Positive-QTOFsplash10-0udi-2389000000-6a1369da7546976c43922021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - UDP-N-acetylmuraminate 10V, Negative-QTOFsplash10-002r-2000059000-71c43c444bd941ed11df2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - UDP-N-acetylmuraminate 20V, Negative-QTOFsplash10-0076-9000041000-bf080a221e01a7a23c052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - UDP-N-acetylmuraminate 40V, Negative-QTOFsplash10-00ec-4129180000-9ce6a724da7e231bce8b2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Prostate Tissue
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Prostate TissueDetected and Quantified0.5 (0.0-1.0) umol/g tissueAdult (>18 years old)Both
Prostate Cancer
details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028404
KNApSAcK IDNot Available
Chemspider ID1136
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1169
PDB IDNot Available
ChEBI ID88385
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]