ChemFOnt: Showing chemical card for CDP-DG(i-21:0/i-21:0) (CFc000096736)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:09:39 UTC

Chemfont ID

CFc000096736

Molecule Identification

Common Name

CDP-DG(i-21:0/i-21:0)

Definition

CDP-DG(i-21:0/i-21:0) is a cytidine diphosphate diacylglycerol or CDP-diacylglycerol (CDP-DG). CDP-diacylglycerol is an important branchpoint intermediate in eukaryotic phospholipid biosynthesis and could be a key regulatory molecule in phospholipid metabolism. It is a glycerophospholipid in which a cytidine diphosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, CDP-diacylglycerols 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. CDP-DG(i-21:0/i-21:0), in particular, consists of one chain of isoheneicosanoic acid at the C-1 position and one chain of isoheneicosanoic acid at the C-2 position. Cytidine diphosphate diacylglycerols are rarely noticed in analyses of lipid compositions of tissues, as they are present is such small amounts (perhaps only 0.05% or so of the total phospholipids).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Isoheneicosanoyl-2-isoheneicosanoyl-sn-glycero-3-CDP	HMDB
1-Isoheneicosanoyl-2-isoheneicosanoyl-sn-glycero-3-cytidine-5'-diphosphate	HMDB
CDP-DG(42:0)	HMDB
CDP-Diacylglycerol(I-21:0/I-21:0)	HMDB
CDP-Diacylglycerol(42:0)	HMDB
({[(2R)-2,3-bis[(19-methylicosanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)({[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinate	HMDB
CDP-DG(i-21:0/i-21:0)	SMPDB

Chemical Formula

C₅₄H₁₀₁N₃O₁₅P₂

Average Molecular Weight

1094.356

Monoisotopic Molecular Weight

1093.67079356

IUPAC Name

{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2,3-bis[(19-methylicosanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid

Traditional Name

[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2,3-bis[(19-methylicosanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCC(C)C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCCCCC(C)C

InChI Identifier

InChI=1S/C54H101N3O15P2/c1-44(2)35-31-27-23-19-15-11-7-5-9-13-17-21-25-29-33-37-49(58)67-41-46(70-50(59)38-34-30-26-22-18-14-10-6-8-12-16-20-24-28-32-36-45(3)4)42-68-73(63,64)72-74(65,66)69-43-47-51(60)52(61)53(71-47)57-40-39-48(55)56-54(57)62/h39-40,44-47,51-53,60-61H,5-38,41-43H2,1-4H3,(H,63,64)(H,65,66)(H2,55,56,62)/t46-,47-,51+,52?,53-/m1/s1

InChI Key

DNVUUBQYLIJFKP-FGLQMSNVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cdp-diacylglycerols. These are glycerolipids containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

CDP-glycerols

Direct Parent

CDP-diacylglycerols

Alternative Parents

Substituents

Cdp-diacylglycerol
Pyrimidine ribonucleoside diphosphate
Diacyl-glycerol-3-pyrophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
Fatty acid ester
Monoalkyl phosphate
Hydroxypyrimidine
Dicarboxylic acid or derivatives
Fatty acyl
Alkyl phosphate
Hydropyrimidine
Pyrimidine
Phosphoric acid ester
Monosaccharide
Organic phosphoric acid derivative
Heteroaromatic compound
Tetrahydrofuran
Carboxylic acid ester
1,2-diol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Organopnictogen compound
Organic oxide
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0116327)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Cardiolipin Biosynthesis CL(a-13:0/a-25:0/i-21:0/i-21:0) (PathBank: SMP0045219)
Cardiolipin Biosynthesis CL(a-13:0/i-13:0/i-21:0/i-21:0) (PathBank: SMP0045860)
Cardiolipin Biosynthesis CL(a-13:0/i-20:0/i-21:0/i-21:0) (PathBank: SMP0048117)
Cardiolipin Biosynthesis CL(a-13:0/i-21:0/i-21:0/i-21:0) (PathBank: SMP0048438)
Cardiolipin Biosynthesis CL(a-13:0/i-22:0/i-21:0/i-21:0) (PathBank: SMP0048761)
Cardiolipin Biosynthesis CL(i-12:0/i-24:0/i-21:0/i-21:0) (PathBank: SMP0054899)
Cardiolipin Biosynthesis CL(i-13:0/i-16:0/i-21:0/i-21:0) (PathBank: SMP0058469)
Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-21:0/i-21:0) (PathBank: SMP0059798)
Cardiolipin Biosynthesis CL(i-14:0/i-13:0/i-21:0/i-21:0) (PathBank: SMP0062253)
Cardiolipin Biosynthesis CL(i-14:0/i-14:0/i-21:0/i-21:0) (PathBank: SMP0062576)
Cardiolipin Biosynthesis CL(a-13:0/i-16:0/i-21:0/i-21:0) (PathBank: SMP0046829)
Cardiolipin Biosynthesis CL(a-13:0/i-24:0/i-21:0/i-21:0) (PathBank: SMP0049084)
Cardiolipin Biosynthesis CL(i-12:0/a-13:0/i-21:0/i-21:0) (PathBank: SMP0049728)
Cardiolipin Biosynthesis CL(i-12:0/a-25:0/i-21:0/i-21:0) (PathBank: SMP0051022)
Cardiolipin Biosynthesis CL(i-12:0/i-13:0/i-21:0/i-21:0) (PathBank: SMP0051671)
Cardiolipin Biosynthesis CL(i-12:0/i-17:0/i-21:0/i-21:0) (PathBank: SMP0052962)
Cardiolipin Biosynthesis CL(i-12:0/i-19:0/i-21:0/i-21:0) (PathBank: SMP0053608)
Cardiolipin Biosynthesis CL(i-12:0/i-20:0/i-21:0/i-21:0) (PathBank: SMP0053932)
Cardiolipin Biosynthesis CL(i-12:0/i-22:0/i-21:0/i-21:0) (PathBank: SMP0054577)
Cardiolipin Biosynthesis CL(i-13:0/18:2(9Z,11Z)/i-21:0/i-21:0) (PathBank: SMP0055223)
Cardiolipin Biosynthesis CL(i-13:0/a-13:0/i-21:0/i-21:0) (PathBank: SMP0055547)
Cardiolipin Biosynthesis CL(i-13:0/a-17:0/i-21:0/i-21:0) (PathBank: SMP0056195)
Cardiolipin Biosynthesis CL(i-13:0/a-25:0/i-21:0/i-21:0) (PathBank: SMP0056846)
Cardiolipin Biosynthesis CL(i-13:0/i-12:0/i-21:0/i-21:0) (PathBank: SMP0057168)
Cardiolipin Biosynthesis CL(i-13:0/i-15:0/i-21:0/i-21:0) (PathBank: SMP0058148)
Cardiolipin Biosynthesis CL(i-13:0/i-17:0/i-21:0/i-21:0) (PathBank: SMP0058795)
Cardiolipin Biosynthesis CL(i-13:0/i-18:0/i-21:0/i-21:0) (PathBank: SMP0059139)
Cardiolipin Biosynthesis CL(i-13:0/i-22:0/i-21:0/i-21:0) (PathBank: SMP0060463)
Cardiolipin Biosynthesis CL(i-14:0/i-15:0/i-21:0/i-21:0) (PathBank: SMP0062916)
Cardiolipin Biosynthesis CL(i-14:0/i-16:0/i-21:0/i-21:0) (PathBank: SMP0063240)
Cardiolipin Biosynthesis CL(a-13:0/18:2(9Z,11Z)/i-21:0/i-21:0) (PathBank: SMP0043605)
Cardiolipin Biosynthesis CL(a-13:0/a-17:0/i-21:0/i-21:0) (PathBank: SMP0044572)
Cardiolipin Biosynthesis CL(a-13:0/a-21:0/i-21:0/i-21:0) (PathBank: SMP0044896)
Cardiolipin Biosynthesis CL(a-13:0/i-12:0/i-21:0/i-21:0) (PathBank: SMP0045541)
Cardiolipin Biosynthesis CL(a-13:0/i-15:0/i-21:0/i-21:0) (PathBank: SMP0046506)
Cardiolipin Biosynthesis CL(a-13:0/i-17:0/i-21:0/i-21:0) (PathBank: SMP0047153)
Cardiolipin Biosynthesis CL(a-13:0/i-18:0/i-21:0/i-21:0) (PathBank: SMP0047474)
Cardiolipin Biosynthesis CL(a-13:0/i-19:0/i-21:0/i-21:0) (PathBank: SMP0047797)
Cardiolipin Biosynthesis CL(i-12:0/18:2(9Z,11Z)/i-21:0/i-21:0) (PathBank: SMP0049407)
Cardiolipin Biosynthesis CL(i-12:0/a-21:0/i-21:0/i-21:0) (PathBank: SMP0050698)
Cardiolipin Biosynthesis CL(i-12:0/i-14:0/i-21:0/i-21:0) (PathBank: SMP0051994)
Cardiolipin Biosynthesis CL(i-12:0/i-18:0/i-21:0/i-21:0) (PathBank: SMP0053285)
Cardiolipin Biosynthesis CL(i-13:0/a-15:0/i-21:0/i-21:0) (PathBank: SMP0055871)
Cardiolipin Biosynthesis CL(i-13:0/a-21:0/i-21:0/i-21:0) (PathBank: SMP0056520)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/i-21:0) (PathBank: SMP0057491)
Cardiolipin Biosynthesis CL(i-13:0/i-19:0/i-21:0/i-21:0) (PathBank: SMP0059463)
Cardiolipin Biosynthesis CL(i-13:0/i-24:0/i-21:0/i-21:0) (PathBank: SMP0060791)
Cardiolipin Biosynthesis CL(i-14:0/i-12:0/i-21:0/i-21:0) (PathBank: SMP0061931)
Cardiolipin Biosynthesis CL(a-13:0/a-13:0/i-21:0/i-21:0) (PathBank: SMP0043928)
Cardiolipin Biosynthesis CL(a-13:0/a-15:0/i-21:0/i-21:0) (PathBank: SMP0044250)
Cardiolipin Biosynthesis CL(a-13:0/i-14:0/i-21:0/i-21:0) (PathBank: SMP0046183)
Cardiolipin Biosynthesis CL(i-12:0/a-15:0/i-21:0/i-21:0) (PathBank: SMP0050053)
Cardiolipin Biosynthesis CL(i-12:0/a-17:0/i-21:0/i-21:0) (PathBank: SMP0050375)
Cardiolipin Biosynthesis CL(i-12:0/i-12:0/i-21:0/i-21:0) (PathBank: SMP0051347)
Cardiolipin Biosynthesis CL(i-12:0/i-15:0/i-21:0/i-21:0) (PathBank: SMP0052316)
Cardiolipin Biosynthesis CL(i-12:0/i-16:0/i-21:0/i-21:0) (PathBank: SMP0052639)
Cardiolipin Biosynthesis CL(i-12:0/i-21:0/i-21:0/i-21:0) (PathBank: SMP0054255)
Cardiolipin Biosynthesis CL(i-13:0/i-14:0/i-21:0/i-21:0) (PathBank: SMP0057823)
Cardiolipin Biosynthesis CL(i-13:0/i-21:0/i-21:0/i-21:0) (PathBank: SMP0060127)
Cardiolipin Biosynthesis CL(i-14:0/a-13:0/i-21:0/i-21:0) (PathBank: SMP0061116)
Cardiolipin Biosynthesis CL(i-14:0/a-15:0/i-21:0/i-21:0) (PathBank: SMP0061440)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00066 g/L	ALOGPS
logP	7.53	ALOGPS
logP	13.69	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-0.032	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	263.27 Å²	ChemAxon
Rotatable Bond Count	50	ChemAxon
Refractivity	286.12 m³·mol⁻¹	ChemAxon
Polarizability	125.65 Å³	ChemAxon
Number of Rings	2	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

HMDB0116327

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

74878040

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131822983

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for CDP-DG(i-21:0/i-21:0) (CFc000096736)

MOL for CFc000096736 (CDP-DG(i-21:0/i-21:0))

3D MOL for CFc000096736 (CDP-DG(i-21:0/i-21:0))

3D SDF for CFc000096736 (CDP-DG(i-21:0/i-21:0))

3D-SDF for CFc000096736 (CDP-DG(i-21:0/i-21:0))

PDB for CFc000096736 (CDP-DG(i-21:0/i-21:0))

3D PDB for CFc000096736 (CDP-DG(i-21:0/i-21:0))

SMILES for CFc000096736 (CDP-DG(i-21:0/i-21:0))

INCHI for CFc000096736 (CDP-DG(i-21:0/i-21:0))

Structure for CFc000096736 (CDP-DG(i-21:0/i-21:0))

3D Structure for CFc000096736 (CDP-DG(i-21:0/i-21:0))