ChemFOnt: Showing chemical card for Tetracosahexaenoyl CoA (CFc000002682)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:37 UTC

Chemfont ID

CFc000002682

Molecule Identification

Common Name

Tetracosahexaenoyl CoA

Definition

(6Z,9Z,12Z,15Z,18Z,21Z)-Tetracosahexaenoyl-CoA is is an intermediate in biosynthesis of unsaturated fatty acids. Tetracosahexaenoyl CoA is the second to last step in the synthesis of docosahexaenoic acid (DHA) and is converted from (9Z,12Z,15Z,18Z,21Z)-Tetracosaheptaenoyl-CoA via the enzyme fatty acid desaturase 2 (EC 1.14.19.-). It is then converted to (4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoyl-CoA via the enzyme enoyl-CoA hydratase (EC 4.2.1.17).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄₅H₇₀N₇O₁₇P₃S

Average Molecular Weight

1106.06

Monoisotopic Molecular Weight

1105.376174075

IUPAC Name

(2R)-4-({[({[(2R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-(tetracosa-6,9,12,15,18,21-hexaenoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid

Traditional Name

(2R)-4-[({[(2R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-(2-{[2-(tetracosa-6,9,12,15,18,21-hexaenoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid

CAS Registry Number

None

SMILES

[H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)CCCCC=CCC=CCC=CCC=CCC=CCC=CCC)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@@]([H])(O)C1([H])OP(O)(O)=O

InChI Identifier

InChI=1S/C45H70N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-36(54)73-29-28-47-35(53)26-27-48-43(57)40(56)45(2,3)31-66-72(63,64)69-71(61,62)65-30-34-39(68-70(58,59)60)38(55)44(67-34)52-33-51-37-41(46)49-32-50-42(37)52/h5-6,8-9,11-12,14-15,17-18,20-21,32-34,38-40,44,55-56H,4,7,10,13,16,19,22-31H2,1-3H3,(H,47,53)(H,48,57)(H,61,62)(H,63,64)(H2,46,49,50)(H2,58,59,60)/t34-,38+,39?,40+,44-/m1/s1

InChI Key

KRIFZIRXAAITHR-LIEWTTMESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Very long-chain fatty acyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside diphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside 3',5'-bisphosphate
Ribonucleoside 3'-phosphate
Pentose-5-phosphate
Pentose phosphate
N-glycosyl compound
Glycosyl compound
Beta amino acid or derivatives
Pentose monosaccharide
Organic pyrophosphate
Monosaccharide phosphate
6-aminopurine
Purine
Imidazopyrimidine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
Alkyl phosphate
Pyrimidine
Phosphoric acid ester
Organic phosphoric acid derivative
N-substituted imidazole
N-acyl-amine
Monosaccharide
Fatty amide
Heteroaromatic compound
Tetrahydrofuran
Imidazole
Azole
Carbothioic s-ester
Thiocarboxylic acid ester
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Sulfenyl compound
Thiocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Peroxisome (HMDB: HMDB0006243)

Source

Exogenous

Exogenous (HMDB: HMDB0006243)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0006243)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.047 g/L	ALOGPS
logP	4.44	ALOGPS
logP	2.25	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	6.44	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	370.61 Å²	ChemAxon
Rotatable Bond Count	36	ChemAxon
Refractivity	281.2 m³·mol⁻¹	ChemAxon
Polarizability	110.45 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023856

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Tetracosahexaenoyl CoA (CFc000002682)

MOL for CFc000002682 (Tetracosahexaenoyl CoA)

3D MOL for CFc000002682 (Tetracosahexaenoyl CoA)

3D SDF for CFc000002682 (Tetracosahexaenoyl CoA)

3D-SDF for CFc000002682 (Tetracosahexaenoyl CoA)

PDB for CFc000002682 (Tetracosahexaenoyl CoA)

3D PDB for CFc000002682 (Tetracosahexaenoyl CoA)

SMILES for CFc000002682 (Tetracosahexaenoyl CoA)

INCHI for CFc000002682 (Tetracosahexaenoyl CoA)

Structure for CFc000002682 (Tetracosahexaenoyl CoA)

3D Structure for CFc000002682 (Tetracosahexaenoyl CoA)