Cannabis Compound Database: Showing Compound Card for CL(16:0/16:0/16:0/16:0) (CDB001260)

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Record Information

Version

1.0

Created at

2020-03-30 18:14:29 UTC

Updated at

2020-12-07 19:08:07 UTC

CannabisDB ID

CDB001260

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

CL(16:0/16:0/16:0/16:0)

Description

CL(16:0/16:0/16:0/16:0), also known as Cardiolipin(64:0) or CL(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(16:0/16:0/16:0/16:0) is considered to be a glycerophosphoglycerophosphoglycerol lipid molecule. CL(16:0/16:0/16:0/16:0) 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,1',2,2'-Tetrahexadecanoyl cardiolipin	ChEBI
1,1',2,2'-Tetrapalmitoyl cardiolipin	ChEBI
Cardiolipin (tetrahexadecanoyl, N-C16:0)	ChEBI
Cardiolipin(16:0/16:0/16:0/16:0)	ChEBI
Cardiolipin(64:0)	ChEBI
CL(1'-[16:0/16:0],3'-[16:0/16:0])	ChEBI
CL(64:0)	ChEBI
Tetrapalmitoyl cardiolipin	ChEBI
1'-[1,2-Dipalmitoyl-rac-glycero-3-phospho],3'-[1,2-dipalmitoyl-rac-glycero-3-phospho]-glycerol	HMDB
1'-[1,2-Dihexadecanoyl-rac-glycero-3-phospho],3'-[1,2-dihexadecanoyl-rac-glycero-3-phospho]-glycerol	HMDB
CL(16:0/16:0/16:0/16:0)	Lipid Annotator

Chemical Formula

C₇₃H₁₄₂O₁₇P₂

Average Molecular Weight

1353.87

Monoisotopic Molecular Weight

1352.9722

IUPAC Name

[(2R)-2,3-bis(hexadecanoyloxy)propoxy][3-({[(2R)-2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid

Traditional Name

(2R)-2,3-bis(hexadecanoyloxy)propoxy(3-{[(2R)-2,3-bis(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid

CAS Registry Number

Not 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)CCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C73H142O17P2/c1-5-9-13-17-21-25-29-33-37-41-45-49-53-57-70(75)83-63-68(89-72(77)59-55-51-47-43-39-35-31-27-23-19-15-11-7-3)65-87-91(79,80)85-61-67(74)62-86-92(81,82)88-66-69(90-73(78)60-56-52-48-44-40-36-32-28-24-20-16-12-8-4)64-84-71(76)58-54-50-46-42-38-34-30-26-22-18-14-10-6-2/h67-69,74H,5-66H2,1-4H3,(H,79,80)(H,81,82)/t68-,69-/m1/s1

InChI Key

GRTNLBQYBYZCCM-ULKDXPJMSA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoglycerophosphoglycerols

Direct Parent

Cardiolipins

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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect:

Touch:

Smooth

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Organ and components:

Heart

Biofluid and excreta:

Blood

Subcellular:

Source:

Biological:

Animal

Role

Biological role:

Industrial application:

Food and nutrition:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	8.83	ALOGPS
logP	23.71	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	1.59	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	236.95 Å²	ChemAxon
Rotatable Bond Count	78	ChemAxon
Refractivity	370.1 m³·mol⁻¹	ChemAxon
Polarizability	165.33 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	CL(16:0/16:0/16:0/16:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0010009000-c851ebbb04f6fa0b11a0	2017-10-05	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0011019000-ab392ddd9ab8f990132e	2017-10-05	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-0096111000-d4b57d2f32c31cb34e08	2017-10-05	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f72-8369033340-27e4d8a739dccb134533	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f72-5394134440-ee360347a8f2651ebc74	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gvt-5394276320-8676457122864338caf9	2017-10-06	View Spectrum