Record Information
Version1.0
Created at2020-04-17 18:41:53 UTC
Updated at2020-11-18 16:38:49 UTC
CannabisDB IDCDB004837
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameUridine diphosphate glucose
DescriptionUridine diphosphate glucose, also known as udpglucose or UDP-alpha-D-glucose, 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. Uridine diphosphate glucose is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine diphosphate glucose exists in all living species, ranging from bacteria to humans. Within humans, uridine diphosphate glucose participates in a number of enzymatic reactions. In particular, galactose 1-phosphate and uridine diphosphate glucose can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate; which is catalyzed by the enzyme galactose-1-phosphate uridylyltransferase. In addition, uridine diphosphate glucose can be biosynthesized from uridine diphosphategalactose through its interaction with the enzyme UDP-glucose 4-epimerase. In humans, uridine diphosphate glucose is involved in galactose metabolism. Outside of the human body, Uridine diphosphate glucose has been detected, but not quantified in, several different foods, such as tea, ostrich ferns, chickpea, cinnamons, and sourdoughs. This could make uridine diphosphate glucose a potential biomarker for the consumption of these foods. Uridine diphosphate glucose is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
GLUCOSE-uridine-C1,5'-diphosphATEChEBI
UDP-D-GlucoseChEBI
UDPglucoseChEBI
URIDINE-5'-diphosphATE-glucoseChEBI
UDP-alpha-D-GlucoseKegg
GLUCOSE-uridine-C1,5'-diphosphoric acidGenerator
URIDINE-5'-diphosphoric acid-glucoseGenerator
UDP-a-D-GlucoseGenerator
UDP-Α-D-glucoseGenerator
Uridine diphosphoric acid glucoseGenerator
Diphosphate glucose, uridineHMDB
Diphosphoglucose, uridineHMDB
Glucose, UDPHMDB
Glucose, uridine diphosphateHMDB
UDP GlucoseHMDB
UDPGHMDB
Uridine diphosphoglucoseHMDB
UDP-GLCHMDB
UDP-GlucoseHMDB
Uridine 5'-(alpha-D-glucopyranosyl pyrophosphate)HMDB
Uridine 5'-(α-D-glucopyranosyl pyrophosphate)HMDB
Uridine 5'-diphosphate glucoseHMDB
Uridine 5'-diphospho-alpha-D-glucoseHMDB
Uridine 5'-diphospho-α-D-glucoseHMDB
Uridine 5'-diphosphoglucoseHMDB
Uridine 5’-(α-D-glucopyranosyl pyrophosphate)HMDB
Uridine 5’-diphosphate glucoseHMDB
Uridine 5’-diphospho-α-D-glucoseHMDB
Uridine 5’-diphosphoglucoseHMDB
Uridine diphospho-D-glucoseHMDB
Uridine pyrophosphate-glucoseHMDB
Uridine diphosphate glucoseChEBI
Chemical FormulaC15H24N2O17P2
Average Molecular Weight566.3
Monoisotopic Molecular Weight566.055
IUPAC Name[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional Nameudp-α-D-glucose
CAS Registry Number133-89-1
SMILES
OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1
InChI KeyHSCJRCZFDFQWRP-JZMIEXBBSA-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
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Urea
  • Secondary alcohol
  • Lactam
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.4ALOGPS
logP-5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area291.54 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.46 m³·mol⁻¹ChemAxon
Polarizability45.39 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSUridine diphosphate glucose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-054k-3933570000-89f658b2d26ff158d84cSpectrum
Predicted GC-MSUridine diphosphate glucose, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-4942706000-3a83736296429f83adeeSpectrum
Predicted GC-MSUridine diphosphate glucose, "Uridine diphosphate glucose,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine diphosphate glucose, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-0000090000-1692ab5f5dad1cf7e4362019-05-22View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-015a-0439510000-69e7cd4c2c365a24706b2019-05-22View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0109-5753970000-03f34041208ba93ef87a2019-05-22View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00fr-9257000000-73b85a465d99ce92467d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00ba-9333000000-b57dc1340555f1a997b42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00fr-9257000000-ba1e6c754b8f04d5b6592021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9000000000-9bd63595c19dbe18d1432021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-4b94aa10fd96d2d9c5052021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-0009000000-996cd4acdaa34c8774602021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901110000-4b81825405869909992e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3911000000-6fd09254750e779631102016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5900000000-03a2a98eb0aa847375302016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4901260000-8396a090c14de7f2d7082016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-8907020000-94410556a0288cb8167b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5901000000-10132c85ad33464d4eef2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0000960000-6404d8d944e1ae6f30e22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07e1-2322960000-6af539ce21752f9023ba2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-9732000000-b0c81adc41b1d799e1e82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-8cab8f2bc0fb9e9e8ba92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057j-9203870000-d60681ff91f741bdb8672021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3519000000-67ca2f9355ef7f94a47d2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 3ENPP36q22O14638 details
Sucrase-isomaltase, intestinalSIP14410 details
TrehalaseTREH11q23.3O43280 details
Procollagen-lysine,2-oxoglutarate 5-dioxygenase 3PLOD37q22O60568 details
Ceramide glucosyltransferaseUGCG9q31Q16739 details
UDP-glucose 4-epimeraseGALE1p36-p35Q14376 details
UDP-glucose 6-dehydrogenaseUGDH4p15.1O60701 details
Dolichyl-phosphate beta-glucosyltransferaseALG513q13.3Q9Y673 details
UTP--glucose-1-phosphate uridylyltransferaseUGP22p14-p13Q16851 details
Glycogen [starch] synthase, liverGYS212p12.2P54840 details
Galactose-1-phosphate uridylyltransferaseGALT9p13P07902 details
Glycogen [starch] synthase, muscleGYS119q13.3P13807 details
Uridine diphosphate glucose pyrophosphataseNUDT1414q32.33O95848 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 3ENPP36q22O14638 details
Procollagen-lysine,2-oxoglutarate 5-dioxygenase 3PLOD37q22O60568 details
UTP--glucose-1-phosphate uridylyltransferaseUGP22p14-p13Q16851 details
Galactose-1-phosphate uridylyltransferaseGALT9p13P07902 details
Glycogenin-1GYG13q24-q25.1P46976 details
Uridine diphosphate glucose pyrophosphataseNUDT1414q32.33O95848 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 3ENPP36q22O14638 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000286
DrugBank IDDB01861
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005660
KNApSAcK IDC00001514
Chemspider IDNot Available
KEGG Compound IDC00029
BioCyc IDCPD-12575
BiGG IDNot Available
Wikipedia LinkUridine_diphosphate_glucose
METLIN IDNot Available
PubChem Compound8629
PDB IDNot Available
ChEBI ID46229
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 23 proteins in total.

Enzymes

General function:
Involved in catalytic activity
Specific function:
Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular weight:
104923.58
General function:
Involved in catalytic activity
Specific function:
Cleaves a variety of phosphodiester and phosphosulfate bonds including deoxynucleotides, nucleotide sugars, and NAD (By similarity).
Gene Name:
ENPP3
Uniprot ID:
O14638
Molecular weight:
100123.54
General function:
Involved in catalytic activity
Specific function:
Plays an important role in the final stage of carbohydrate digestion. Isomaltase activity is specific for both alpha-1,4- and alpha-1,6-oligosaccharides.
Gene Name:
SI
Uniprot ID:
P14410
Molecular weight:
Not Available
General function:
Involved in catalytic activity
Specific function:
Intestinal trehalase is probably involved in the hydrolysis of ingested trehalose.
Gene Name:
TREH
Uniprot ID:
O43280
Molecular weight:
66567.26
General function:
Involved in oxidoreductase activity
Specific function:
Forms hydroxylysine residues in -Xaa-Lys-Gly- sequences in collagens. These hydroxylysines serve as sites of attachment for carbohydrate units and are essential for the stability of the intermolecular collagen cross-links.
Gene Name:
PLOD3
Uniprot ID:
O60568
Molecular weight:
84784.505
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Catalyzes the first glycosylation step in glycosphingolipid biosynthesis, the transfer of glucose to ceramide. May also serve as a "flippase".
Gene Name:
UGCG
Uniprot ID:
Q16739
Molecular weight:
44853.255
General function:
Involved in catalytic activity
Specific function:
Catalyzes two distinct but analogous reactions: the epimerization of UDP-glucose to UDP-galactose and the epimerization of UDP-N-acetylglucosamine to UDP-N-acetylgalactosamine.
Gene Name:
GALE
Uniprot ID:
Q14376
Molecular weight:
38281.435
General function:
Involved in oxidoreductase activity
Specific function:
Involved in the biosynthesis of glycosaminoglycans; hyaluronan, chondroitin sulfate, and heparan sulfate.
Gene Name:
UGDH
Uniprot ID:
O60701
Molecular weight:
47602.08
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Not Available
Gene Name:
ALG5
Uniprot ID:
Q9Y673
Molecular weight:
33524.965
General function:
Involved in nucleotidyltransferase activity
Specific function:
Plays a central role as a glucosyl donor in cellular metabolic pathways.
Gene Name:
UGP2
Uniprot ID:
Q16851
Molecular weight:
55676.36

Only showing the first 10 proteins. There are 23 proteins in total.