ChemFOnt: Showing chemical card for 2-trans,4-trans-Octadienoyl-CoA (CFc000001546)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:12 UTC

Chemfont ID

CFc000001546

Molecule Identification

Common Name

2-trans,4-trans-Octadienoyl-CoA

Definition

2-trans,4-trans-Octadienoyl-CoA is an intermediate within the mitochondrial metabolism pathway responsible for the beta-oxidation of unsaturated fatty acids with double bonds extending from odd-numbered carbon atoms. (PMID: 1495956 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
S-[2E,4E]-Octadienoate	HMDB
S-[2E,4E]-Octadienoate CoA	HMDB
S-[2E,4E]-Octadienoate coenzyme A	HMDB
S-[2E,4E]-Octadienoic acid	HMDB
4-({[({[(2R,3S,4R,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-[(2E,4E)-octa-2,4-dienoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidate	Generator, HMDB
4-({[({[(2R,3S,4R,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-[(2E,4E)-octa-2,4-dienoylsulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidate	Generator, HMDB
4-({[({[(2R,3S,4R,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-[(2E,4E)-octa-2,4-dienoylsulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid	Generator, HMDB

Chemical Formula

C₂₉H₄₆N₇O₁₇P₃S

Average Molecular Weight

889.699

Monoisotopic Molecular Weight

889.188373307

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2E,4E)-octa-2,4-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2E,4E)-octa-2,4-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

74418-29-4

SMILES

CCC\C=C\C=C\C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(=O)O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C29H46N7O17P3S/c1-4-5-6-7-8-9-20(38)57-13-12-31-19(37)10-11-32-27(41)24(40)29(2,3)15-50-56(47,48)53-55(45,46)49-14-18-23(52-54(42,43)44)22(39)28(51-18)36-17-35-21-25(30)33-16-34-26(21)36/h6-9,16-18,22-24,28,39-40H,4-5,10-15H2,1-3H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/b7-6+,9-8+/t18-,22-,23-,24?,28-/m1/s1

InChI Key

HOQIPZYVEOMJGX-LEIHBCTOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a medium-chain 2-enoyl chain of 5 to 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Medium-chain 2-enoyl CoAs

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002289)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002289)

Source

Endogenous

Endogenous (HMDB: HMDB0002289)

Animal

Animal (HMDB: HMDB0002289)

Exogenous

Food

Food (HMDB: HMDB0002289)

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)

Exogenous (HMDB: HMDB0002289)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002289)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002289)

Lipid metabolism pathway (HMDB: HMDB0002289)

Cellular process

Cell signaling (HMDB: HMDB0002289)

Biochemical process

Lipid transport (HMDB: HMDB0002289)

Role

Biological role

Energy source (HMDB: HMDB0002289)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002289)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.45 g/L	ALOGPS
logP	0.61	ALOGPS
logP	-4.2	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	202.05 m³·mol⁻¹	ChemAxon
Polarizability	82.56 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

HMDB0002289

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022951

KNApSAcK ID

Not Available

Chemspider ID

13628330

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6596

PubChem Compound

21252282

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2-trans,4-trans-Octadienoyl-CoA (CFc000001546)

MOL for CFc000001546 (2-trans,4-trans-Octadienoyl-CoA)

3D MOL for CFc000001546 (2-trans,4-trans-Octadienoyl-CoA)

3D SDF for CFc000001546 (2-trans,4-trans-Octadienoyl-CoA)

3D-SDF for CFc000001546 (2-trans,4-trans-Octadienoyl-CoA)

PDB for CFc000001546 (2-trans,4-trans-Octadienoyl-CoA)

3D PDB for CFc000001546 (2-trans,4-trans-Octadienoyl-CoA)

SMILES for CFc000001546 (2-trans,4-trans-Octadienoyl-CoA)

INCHI for CFc000001546 (2-trans,4-trans-Octadienoyl-CoA)

Structure for CFc000001546 (2-trans,4-trans-Octadienoyl-CoA)

3D Structure for CFc000001546 (2-trans,4-trans-Octadienoyl-CoA)