UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine (PAMDB006333)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB006333
Identification
Name: UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine
Description:UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosamine is an intermediate in lipid IVA biosynthesis pathway in E.coli. It is a substrate for the enzyme UDP-2,3-diacylglucosamine hydrolase which catalyzes the reaction UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosamine + H2O -> 2,3-bis[(3R)-3-hydroxymyristoyl]-alpha-D-glucosaminyl 1-phosphate + UMP + 2 H+. It is also a product for enzyme UDP-3-O-(R-3-hydroxymyristoyl)-glucosamine N-acyltransferase which catalyzes reaction a (3R)-3-hydroxymyristoyl-[acp] + UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine -> UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosamine + a holo-[acyl-carrier protein] + H+ (BioCyc compound: OH-MYRISTOYL).
Structure
Thumb
Synonyms:Not Available
Chemical Formula: C43H77N3O20P2
Average Molecular Weight: 1018.038
Monoisotopic Molecular Weight: 1017.457565887
InChI Key: KOJCFMYSTWNMQW-LNGUGUEYSA-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:Not Available
Traditional IUPAC Name: Not Available
SMILES:[H]C(O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([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)CC([H])(O)CCCCCCCCCCC
Chemical Taxonomy
Taxonomy DescriptionNot Available
Kingdom Not Available
Super ClassNot Available
Class Not Available
Sub ClassNot Available
Direct Parent Not Available
Alternative Parents Not Available
Substituents Not Available
Molecular Framework Not Available
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:Not Available
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine + (3R)-3-hydroxymyristoyl-[acp] > Hydrogen ion + a holo-[acyl-carrier protein] + UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine
UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine + Water > Uridine 5'-monophosphate + Hydrogen ion + 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate
2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate + UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine > Uridine 5'-diphosphate + Hydrogen ion + (2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate)
SMPDB Pathways:
Lipopolysaccharide biosynthesisPW000831 Pw000831Pw000831 greyscalePw000831 simple
lipopolysaccharide biosynthesis IIPW001905 Pw001905Pw001905 greyscalePw001905 simple
lipopolysaccharide biosynthesis IIIPW002059 Pw002059Pw002059 greyscalePw002059 simple
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine + (3R)-3-hydroxymyristoyl-[acp] > Hydrogen ion + a holo-[acyl-carrier protein] + UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine
UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine + Water > Uridine 5'-monophosphate + Hydrogen ion + 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate
2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate + UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine > Uridine 5'-diphosphate + Hydrogen ion + (2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 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: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink