ChemFOnt: Showing chemical card for PA(i-21:0/a-21:0) (CFc000096285)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:08:59 UTC

Chemfont ID

CFc000096285

Molecule Identification

Common Name

PA(i-21:0/a-21:0)

Definition

PA(i-21:0/a-21:0) 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(i-21:0/a-21:0), in particular, consists of one chain of isoheneicosanoic acid at the C-1 position and one chain of anteisoheneicosanoic acid at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Isoheneicosanoyl-2-anteisoheneicosanoyl-sn-glycero-3-phosphate	HMDB
1-Isoheneicosanoyl-2-anteisoheneicosanoyl-sn-phosphatidic acid	HMDB
PA(42:0)	HMDB
Phosphatidic acid(i-21:0/a-21:0)	HMDB
Phosphatidic acid(42:0)	HMDB
Phosphatidate(I-21:0/A-21:0)	HMDB
Phosphatidate(42:0)	HMDB
[(2R)-2-[(18-Methylicosanoyl)oxy]-3-[(19-methylicosanoyl)oxy]propoxy]phosphonate	HMDB
PA(i-21:0/a-21:0)	SMPDB

Chemical Formula

C₄₅H₈₉O₈P

Average Molecular Weight

789.173

Monoisotopic Molecular Weight

788.629506824

IUPAC Name

[(2R)-2-[(18-methylicosanoyl)oxy]-3-[(19-methylicosanoyl)oxy]propoxy]phosphonic acid

Traditional Name

(2R)-2-[(18-methylicosanoyl)oxy]-3-[(19-methylicosanoyl)oxy]propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCC(C)C)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCC(C)CC

InChI Identifier

InChI=1S/C45H89O8P/c1-5-42(4)36-32-28-24-20-16-12-9-10-14-18-22-26-30-34-38-45(47)53-43(40-52-54(48,49)50)39-51-44(46)37-33-29-25-21-17-13-8-6-7-11-15-19-23-27-31-35-41(2)3/h41-43H,5-40H2,1-4H3,(H2,48,49,50)/t42?,43-/m1/s1

InChI Key

PSDJHTOALMPPJI-XFCPCMSTSA-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

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0115876)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/10:0) (PathBank: SMP0041172)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/12:0) (PathBank: SMP0041173)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/13:0) (PathBank: SMP0041174)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/14:0) (PathBank: SMP0041175)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/15:0) (PathBank: SMP0041176)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/16:0) (PathBank: SMP0041177)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/17:0) (PathBank: SMP0041178)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/18:0) (PathBank: SMP0041179)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/19:0) (PathBank: SMP0041180)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/20:0) (PathBank: SMP0041181)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/21:0) (PathBank: SMP0041182)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/22:0) (PathBank: SMP0041183)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/8:0) (PathBank: SMP0041184)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/a-13:0) (PathBank: SMP0041185)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/a-15:0) (PathBank: SMP0041186)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/a-17:0) (PathBank: SMP0041187)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/a-21:0) (PathBank: SMP0041188)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/a-25:0) (PathBank: SMP0041189)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/i-12:0) (PathBank: SMP0041190)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/i-13:0) (PathBank: SMP0041191)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/i-14:0) (PathBank: SMP0041192)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/i-15:0) (PathBank: SMP0041193)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/i-16:0) (PathBank: SMP0041194)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/i-17:0) (PathBank: SMP0041195)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/i-18:0) (PathBank: SMP0041196)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/i-19:0) (PathBank: SMP0041197)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/i-20:0) (PathBank: SMP0041198)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/i-22:0) (PathBank: SMP0041199)
De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-21:0/i-24:0) (PathBank: SMP0041200)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.6e-05 g/L	ALOGPS
logP	9.83	ALOGPS
logP	16.01	ChemAxon
logS	-7.3	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	44	ChemAxon
Refractivity	224.48 m³·mol⁻¹	ChemAxon
Polarizability	101.3 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

External Links

HMDB ID

HMDB0115876

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

74877614

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131822532

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for PA(i-21:0/a-21:0) (CFc000096285)

MOL for CFc000096285 (PA(i-21:0/a-21:0))

3D MOL for CFc000096285 (PA(i-21:0/a-21:0))

3D SDF for CFc000096285 (PA(i-21:0/a-21:0))

3D-SDF for CFc000096285 (PA(i-21:0/a-21:0))

PDB for CFc000096285 (PA(i-21:0/a-21:0))

3D PDB for CFc000096285 (PA(i-21:0/a-21:0))

SMILES for CFc000096285 (PA(i-21:0/a-21:0))

INCHI for CFc000096285 (PA(i-21:0/a-21:0))

Structure for CFc000096285 (PA(i-21:0/a-21:0))

3D Structure for CFc000096285 (PA(i-21:0/a-21:0))