Cannabis Compound Database: Showing Compound Card for PGP(18:1(11Z)/18:3(6Z,9Z,12Z)) (CDB001240)

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Record Information

Version

1.0

Created at

2020-03-30 18:13:08 UTC

Updated at

2020-12-07 19:08:04 UTC

CannabisDB ID

CDB001240

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

PGP(18:1(11Z)/18:3(6Z,9Z,12Z))

Description

PGP(18:1(11Z)/18:3(6Z,9Z,12Z)) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(18:1(11Z)/18:3(6Z,9Z,12Z)), in particular, consists of one 11Z-octadecenoyl chain to the C-1 atom, and one 6Z,9Z,12Z-octadecatrienoyl to the C-2 atom. In E. coli, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase. 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
PGP(18:1(11Z)/18:3(6Z,9Z,12Z))	Lipid Annotator
3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid	Lipid Annotator, HMDB
1-vaccenoyl-2-g-linolenoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	Lipid Annotator, HMDB
PGP(18:1/18:3)	Lipid Annotator, HMDB
1-(11Z-octadecenoyl)-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	Lipid Annotator, HMDB
PGP(36:4)	Lipid Annotator, HMDB
1-Vaccenoyl-2-gamma-linolenoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	HMDB
PGP(18:1n7/18:3n6)	HMDB
PGP(18:1W7/18:3W6)	HMDB

Chemical Formula

C₄₂H₇₆O₁₃P₂

Average Molecular Weight

850.99

Monoisotopic Molecular Weight

850.4761

IUPAC Name

[(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid

Traditional Name

(2S)-2-hydroxy-3-{[hydroxy((2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H]O[C@@]([H])(C([H])([H])OP(=O)(O[H])O[H])C([H])([H])OP(=O)(O[H])OC([H])([H])[C@]([H])(OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C42H76O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(44)51-37-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)55-42(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12-15,18,20,24,26,39-40,43H,3-11,16-17,19,21-23,25,27-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b14-12-,15-13-,20-18-,26-24-/t39-,40+/m0/s1

InChI Key

LLCJUQDDGDERCH-FJNFSWOHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoglycerophosphates

Direct Parent

Phosphatidylglycerophosphates

Alternative Parents

Substituents

Diacylglycerophosphoglycerophosphate
Sn-glycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Blood

Tissue and substructures:

All tissues

Cell and elements:

Extracellular

Subcellular:

Role

Industrial application:

Food and nutrition:

Biological role:

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	7.28	ALOGPS
logP	11.14	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	1.35	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	195.35 Å²	ChemAxon
Rotatable Bond Count	42	ChemAxon
Refractivity	229.05 m³·mol⁻¹	ChemAxon
Polarizability	95.22 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

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0n9r-1391081260-bd5bf4bfd74e009473e1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-082a-2392032110-73d83809860029d55abd	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9466151300-84299a035744d2a53ef9	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01u1-3090020020-589c43b982b34ba4c5dd	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9050000000-0e76393f09e34e962b04	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9010000000-c1c8c7bd8c1999892a88	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000000090-40abed2e3880a3dd0c54	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-7090032050-a8fb177ed358b9e6b41e	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-6090000000-cb579b33e50ece86c97b	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udj-3011090870-b3f0d5423bb3db74f437	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfs-1400036900-96687e25a64e0acc8acc	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0100920000-572b61130d30c5f76cb3	2021-09-25	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0013523

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029523

KNApSAcK ID

Not Available

Chemspider ID

35032701

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481841

PDB ID

Not Available

ChEBI ID

Not Available

References

General References

Not Available

Showing Compound Card for PGP(18:1(11Z)/18:3(6Z,9Z,12Z)) (CDB001240)

Structure for CDB001240 (PGP(18:1(11Z)/18:3(6Z,9Z,12Z)))