Cannabis Compound Database: Showing Compound Card for PA(16:0/22:0) (CDB003016)

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Record Information

Version

1.0

Created at

2020-03-30 20:16:17 UTC

Updated at

2020-12-07 19:10:19 UTC

CannabisDB ID

CDB003016

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

PA(16:0/22:0)

Description

PA(16:0/22:0) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(16:0/22:0), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one docosanoyl to the C-2 atom. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. 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-Palmitoyl-2-behenoyl-sn-glycero-3-phosphate	HMDB
1-Palmitoyl-2-behenoyl-sn-phosphatidic acid	HMDB
PA(38:0)	HMDB
Phosphatidic acid(16:0/22:0)	HMDB
Phosphatidic acid(38:0)	HMDB
Phosphatidate(16:0/22:0)	HMDB
Phosphatidate(38:0)	HMDB
1-palmitoyl-2-behenoyl-sn-glycero-3-phosphate	SMPDB, HMDB
1-palmitoyl-2-behenoyl-sn-phosphatidic acid	SMPDB, HMDB
PA(38:0)	SMPDB, HMDB
Phosphatidic acid(16:0/22:0)	SMPDB, HMDB
Phosphatidic acid(38:0)	SMPDB, HMDB
Phosphatidate(16:0/22:0)	SMPDB, HMDB
PA(16:0/22:0)	SMPDB

Chemical Formula

C₄₁H₈₁O₈P

Average Molecular Weight

733.07

Monoisotopic Molecular Weight

732.5669

IUPAC Name

[(2R)-2-(docosanoyloxy)-3-(hexadecanoyloxy)propoxy]phosphonic acid

Traditional Name

(2R)-2-(docosanoyloxy)-3-(hexadecanoyloxy)propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C41H81O8P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-41(43)49-39(38-48-50(44,45)46)37-47-40(42)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h39H,3-38H2,1-2H3,(H2,44,45,46)/t39-/m1/s1

InChI Key

IKTMUTGHQRTXAH-LDLOPFEMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1,2-diacylglycerol-3-phosphates

Alternative Parents

Substituents

1,2-diacylglycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Dicarboxylic acid or derivatives
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphates (LMGP10010971 )

Ontology

Physiological effect

Organoleptic effect:

Touch:

Smooth

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Blood

Subcellular:

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	9.6	ALOGPS
logP	14.55	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	42	ChemAxon
Refractivity	206.18 m³·mol⁻¹	ChemAxon
Polarizability	93.49 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	splash10-0083-1169302500-76c92ea9aaf48fcb547e	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-3397103100-f2fe95c963ef2771d8ac	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ot-1294024000-e104b809410be9035d68	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052r-4095200300-6201dfc66b559549dbdb	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9050000000-c60f6534ba6c7ad91de6	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-399e227fd1847eff877c	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0000000900-10746a3c22d7c4446b6b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001r-0000005900-84de080f8ec089046cdc	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002u-0006609300-6bdd1af01025ca97d2a8	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000900-e09378df2d3942cf355c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000009900-f5a47f8411b3a51c5d29	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aos-0000922400-4506c6915e42dd4a2a4b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000900-7697f25f15a1cbc32c41	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-055o-0039500500-a8273e5eb586c25ecd2f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-1197400100-6ba80f39d5e24942eb5f	2021-09-23	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/16:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/18:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/20:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/24:0)		Not Available