Showing Compound Card for CL(16:0/16:0/16:0/18:2(9Z,12Z)) (CDB001264)

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Record Information
Version1.0
Created at2020-03-30 18:14:46 UTC
Updated at2020-12-07 19:08:07 UTC
CannabisDB IDCDB001264
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCL(16:0/16:0/16:0/18:2(9Z,12Z))
DescriptionCL(16:0/16:0/16:0/18:2(9Z,12Z)), also known as CL(64:0) or Cardiolipin(64:0), belongs to the class of organic compounds known as cardiolipins. These are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,2-diacylglycerol chain. Their general formula is OC(COP(O)(=O)OC[C@@H](CO[R1])O[R2])COP(O)(=O)OC[C@@H](CO[R3])O[R4], where R1-R4 are four fatty acyl chains. Thus, CL(16:0/16:0/16:0/18:2(9Z,12Z)) is considered to be a glycerophosphoglycerophosphoglycerol lipid molecule. CL(16:0/16:0/16:0/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. This compound is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CL(64:0)HMDB
Cardiolipin(64:0)HMDB
CL(16:0/16:0/16:0/16:0)HMDB
Cardiolipin(16:0/16:0/16:0/16:0)HMDB
1'-[1,2-Dipalmitoyl-rac-glycero-3-phospho],3'-[1,2-dipalmitoyl-rac-glycero-3-phospho]-glycerolHMDB
1'-[1,2-Dihexadecanoyl-rac-glycero-3-phospho],3'-[1,2-dihexadecanoyl-rac-glycero-3-phospho]-glycerolHMDB
CL(1'-[16:0/16:0],3'-[16:0/16:0])HMDB
CL(16:0/16:0/16:0/18:2(9Z,12Z))Lipid Annotator
Chemical FormulaC75H142O17P2
Average Molecular Weight1377.89
Monoisotopic Molecular Weight1376.9722
IUPAC Name[3-({[(2R)-2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid
Traditional Name3-{[(2R)-2,3-bis(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C75H142O17P2/c1-5-9-13-17-21-25-29-33-34-38-42-46-50-54-58-62-75(80)92-71(66-86-73(78)60-56-52-48-44-40-36-31-27-23-19-15-11-7-3)68-90-94(83,84)88-64-69(76)63-87-93(81,82)89-67-70(91-74(79)61-57-53-49-45-41-37-32-28-24-20-16-12-8-4)65-85-72(77)59-55-51-47-43-39-35-30-26-22-18-14-10-6-2/h21,25,33-34,69-71,76H,5-20,22-24,26-32,35-68H2,1-4H3,(H,81,82)(H,83,84)/b25-21-,34-33-/t69-,70+,71+/m0/s1
InChI KeyUMGKKHKOBCUCDP-JDVAIEAXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cardiolipins. These are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,2-diacylglycerol chain. Their general formula is OC(COP(O)(=O)OC[C@@H](CO[R1])O[R2])COP(O)(=O)OC[C@@H](CO[R3])O[R4], where R1-R4 are four fatty acyl chains.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerophosphoglycerols
Direct ParentCardiolipins
Alternative Parents
Substituents
  • Cardiolipin
  • Tetracarboxylic acid or derivatives
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Biological 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
logP8.97ALOGPS
logP23.88ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)1.59ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area236.95 ŲChemAxon
Rotatable Bond Count78ChemAxon
Refractivity381.54 m³·mol⁻¹ChemAxon
Polarizability164.89 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCL(16:0/16:0/16:0/18:2(9Z,12Z)), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0030009000-1a00adb44a5788e709ee2017-10-05View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0031119000-6f7f3ddad359f1cc6d022017-10-05View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0atc-0093300000-e3b1dfb4085aab796ff42017-10-05View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-2976040440-18954b82228039e929bb2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-1593133350-6cc42274cdfd01307a4d2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-2288393410-e7489cacbe800672b1df2017-10-06View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0056392
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031420
KNApSAcK IDNot Available
Chemspider ID74854725
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound118701908
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available