Showing Compound Card for CDP-DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) (CDB003322)

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Record Information
Version1.0
Created at2020-03-30 20:36:47 UTC
Updated at2020-11-18 16:38:17 UTC
CannabisDB IDCDB003322
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCDP-DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))
DescriptionCDP-DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) belongs to the family of CDP-diacylglycerols. It is a glycerophospholipid containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. CDP-DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)), in particular, consists of two 9Z,12Z-octadecadienoyl chain at positions C-1 and C2. In E. coli glycerophospholipid metabolism, The biosynthesis of CDP-diacylglycerol (CDP-DG) involves condensation of phosphatidic acid (PA) and cytidine triphosphate, with elimination of pyrophosphate, catalysed by the enzyme CDP-diacylglycerol synthase. The resulting CDP-diacylglycerol can be utilized immediately for the synthesis of phosphatidylglycerol (PG), and thence cardiolipin (CL), and of phosphatidylinositol (PI). CDP-DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. This compound is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Linoleoyl-2-alpha-linolenoyl-sn-glycero-3-CDPHMDB
1-Linoleoyl-2-alpha-linolenoyl-sn-glycero-3-cytidine-5'-diphosphateHMDB
CDP-DG(18:2/18:3)HMDB
CDP-DG(18:2N6/18:3N3)HMDB
CDP-DG(18:2W6/18:3W3)HMDB
CDP-DG(36:5)HMDB
CDP-Diacylglycerol(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))HMDB
CDP-Diacylglycerol(18:2/18:3)HMDB
CDP-Diacylglycerol(18:2N6/18:3N3)HMDB
CDP-Diacylglycerol(18:2W6/18:3W3)HMDB
CDP-Diacylglycerol(36:5)HMDB
{[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({hydroxy[(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)phosphinateHMDB
1-linoleoyl-2-alpha-linolenoyl-sn-glycero-3-CDP SMPDB, HMDB
1-linoleoyl-2-alpha-linolenoyl-sn-glycero-3-cytidine-5'-diphosphate SMPDB, HMDB
CDP-DG(18:2/18:3) SMPDB, HMDB
CDP-DG(18:2n6/18:3n3) SMPDB, HMDB
CDP-DG(18:2w6/18:3w3) SMPDB, HMDB
CDP-DG(36:5) SMPDB, HMDB
CDP-diacylglycerol(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) SMPDB, HMDB
CDP-diacylglycerol(18:2/18:3) SMPDB, HMDB
CDP-diacylglycerol(18:2n6/18:3n3) SMPDB, HMDB
CDP-diacylglycerol(18:2w6/18:3w3) SMPDB, HMDB
CDP-DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))SMPDB
Chemical FormulaC48H79N3O15P2
Average Molecular Weight1000.11
Monoisotopic Molecular Weight999.4986
IUPAC Name{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)phosphinic acid
Traditional Name[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([hydroxy((2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy)phosphoryl]oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C48H79N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-43(52)61-37-40(64-44(53)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)38-62-67(57,58)66-68(59,60)63-39-41-45(54)46(55)47(65-41)51-36-35-42(49)50-48(51)56/h6,8,11-14,17-20,35-36,40-41,45-47,54-55H,3-5,7,9-10,15-16,21-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b8-6-,13-11-,14-12-,19-17-,20-18-/t40-,41-,45+,46?,47-/m1/s1
InChI KeyYHTBZVGNGPLEPT-HVCBFHICSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cdp-diacylglycerols. These are glycerolipids containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassCDP-glycerols
Direct ParentCDP-diacylglycerols
Alternative Parents
Substituents
  • Cdp-diacylglycerol
  • Pyrimidine ribonucleoside diphosphate
  • Diacyl-glycerol-3-pyrophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Aminopyrimidine
  • Fatty acid ester
  • Pyrimidone
  • Monoalkyl phosphate
  • Imidolactam
  • Pyrimidine
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Dicarboxylic acid or derivatives
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Amino acid or derivatives
  • 1,2-diol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Alcohol
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Amine
  • Carbonyl group
  • Primary amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.62ALOGPS
logP9.53ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-0.032ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area263.27 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity264.2 m³·mol⁻¹ChemAxon
Polarizability106.18 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCDP-DG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0910000100-78f57906682b7ab608d32019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1910000100-1568184ac23ef59ed2442019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3921000100-ddef5301b22d65e8761c2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08i0-0890000404-122963325377cdabf7d22019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-5692300301-2b62e477ce317d1a47692019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvi-5911000000-83ea6cdaddeb54e0776f2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000209-4c3453cf1fbffd93836f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01tc-6090700400-dfe090e27e055047513c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ai-5329400402-e08e5ada9af6f560a96f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-8101010049-705beaed976abdb5a0142021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02l0-0100000069-dabd523dc780a14a85b62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0157910000-7bf614a03490ef0cf0342021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0115971
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB095761
KNApSAcK IDNot Available
Chemspider ID74877709
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131822627
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available