ChemFOnt: Showing chemical card for 3-Oxooctanoyl-CoA (CFc000002002)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:46 UTC

Chemfont ID

CFc000002002

Molecule Identification

Common Name

3-Oxooctanoyl-CoA

Definition

3-Oxooctanoyl-CoA is the substrate of the acetyl-CoA C-acyltransferase/oxoacyl-CoA thiolase A (EC 2.3.1.16, SCP2/3-oxoacyl-CoA thiolase) present in peroxisomes from normal liver. Peroxisomes beta -oxidize a wide variety of substrates including straight chain fatty acids, 2-methyl-branched fatty acids, and the side chain of the bile acid intermediates di- and trihydroxycoprostanic acids. Peroxisomes contain several beta -oxidation pathways with different substrate specificities; or example, straight chain acyl-CoAs are desaturated by palmitoyl-CoA oxidase, and their enoyl-CoAs are then converted to 3-oxoacyl-CoAs by MFP-1, which forms (hydration) and dehydrogenates L-3(3S)-hydroxyacyl-CoAs; for example, straight chain acyl-CoAs are desaturated by palmitoyl-CoA oxidase (23), and their enoyl-CoAs are then converted to 3-oxoacyl-CoAs by 3-hydroxyacyl-CoA dehydrogenase (EC 1.1.1.35), which forms (hydration) and dehydrogenates L-3(3S)-hydroxyacyl-CoAs and their enoyl-CoAs are then converted to the corresponding 3-oxoacyl-CoAs by long-chain-enoyl-CoA hydratase(EC 4.2.1.74), which forms and dehydrogenates D-3(3R)-hydroxyacyl-CoAs. (PMID: 9325339 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Ketooctanoyl-CoA	HMDB
3-Ketooctanoyl-coenzyme A	HMDB
3-Oxooctanoyl coenzyme A	HMDB
3-Oxooctanoyl-coenzyme A	HMDB
S-(3-Oxooctanoate	HMDB
S-(3-Oxooctanoate) CoA	HMDB
S-(3-Oxooctanoate) coenzyme A	HMDB
S-(3-Oxooctanoic acid	HMDB

Chemical Formula

C₂₉H₄₈N₇O₁₈P₃S

Average Molecular Weight

907.714

Monoisotopic Molecular Weight

907.198937993

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-[(3-oxooctanoyl)sulfanyl]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-[(3-oxooctanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

54684-64-9

SMILES

CCCCCC(=O)CC(=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=C(N)N=CN=C12

InChI Identifier

InChI=1S/C29H48N7O18P3S/c1-4-5-6-7-17(37)12-20(39)58-11-10-31-19(38)8-9-32-27(42)24(41)29(2,3)14-51-57(48,49)54-56(46,47)50-13-18-23(53-55(43,44)45)22(40)28(52-18)36-16-35-21-25(30)33-15-34-26(21)36/h15-16,18,22-24,28,40-41H,4-14H2,1-3H3,(H,31,38)(H,32,42)(H,46,47)(H,48,49)(H2,30,33,34)(H2,43,44,45)/t18-,22-,23-,24?,28-/m1/s1

InChI Key

WPIVBCGRGVNDDT-FFJUWABQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

3-oxo-acyl 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
1,3-dicarbonyl compound
Imidolactam
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Ketone
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
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Fatty acyl CoAs (C05267 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0003941)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003941)

Source

Endogenous

Endogenous (HMDB: HMDB0003941)

Animal

Animal (HMDB: HMDB0003941)

Exogenous

Food

Food (HMDB: HMDB0003941)

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: HMDB0003941)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0003941)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0003941)
Fatty Acid Metabolism (PathBank: SMP0063589)
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids (PathBank: SMP0063640)
Fatty Acid Elongation In Mitochondria (PathBank: SMP0087294)
Fatty Acid Metabolism (PathBank: SMP0002361)
Fatty Acid Elongation In Mitochondria (PathBank: SMP0002368)
Fatty Acid Elongation (PathBank: SMP0121069)
Fatty Acid Oxidation (Octanoate) (PathBank: SMP0121351)
Fatty Acid Elongation In Mitochondria (PathBank: SMP0063612)
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids (HMDB: HMDB0003941)

Disease pathway

Very-Long-Chain Acyl-CoA Dehydrogenase Deficiency (VLCAD) (PathBank: SMP0120824)
Carnitine Palmitoyl Transferase Deficiency II (PathBank: SMP0120825)
Long-Chain-3-Hydroxyacyl-CoA Dehydrogenase Deficiency (LCHAD) (PathBank: SMP0120827)
Ethylmalonic Encephalopathy (HMDB: HMDB0003941)
Trifunctional Protein Deficiency (PathBank: SMP0120609)
Ethylmalonic Encephalopathy (PathBank: SMP0120696)
Carnitine Palmitoyl Transferase Deficiency I (PathBank: SMP0120822)
Long Chain Acyl-CoA Dehydrogenase Deficiency (LCAD) (PathBank: SMP0120604)
Medium Chain Acyl-CoA Dehydrogenase Deficiency (MCAD) (PathBank: SMP0120607)
Short-Chain Acyl-CoA Dehydrogenase Deficiency (SCAD Deficiency) (PathBank: SMP0120740)
Glutaric Aciduria Type I (PathBank: SMP0000185)

Lipid metabolism pathway (HMDB: HMDB0003941)

Cellular process

Cell signaling (HMDB: HMDB0003941)

Biochemical process

Lipid transport (HMDB: HMDB0003941)

Role

Biological role

Energy source (HMDB: HMDB0003941)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0003941)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.07 g/L	ALOGPS
logP	0.23	ALOGPS
logP	-4.7	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	380.7 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	200.53 m³·mol⁻¹	ChemAxon
Polarizability	81.88 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

HMDB0003941

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023260

KNApSAcK ID

Not Available

Chemspider ID

389506

KEGG Compound ID

C05267

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440608

PDB ID

Not Available

ChEBI ID

28264

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Thorpe, Colin. A method for the preparation of 3-ketoacyl-CoA derivatives. Analytical Biochemistry (1986), 155(2), 391-4.

Showing chemical card for 3-Oxooctanoyl-CoA (CFc000002002)

MOL for CFc000002002 (3-Oxooctanoyl-CoA)

3D MOL for CFc000002002 (3-Oxooctanoyl-CoA)

3D SDF for CFc000002002 (3-Oxooctanoyl-CoA)

3D-SDF for CFc000002002 (3-Oxooctanoyl-CoA)

PDB for CFc000002002 (3-Oxooctanoyl-CoA)

3D PDB for CFc000002002 (3-Oxooctanoyl-CoA)

SMILES for CFc000002002 (3-Oxooctanoyl-CoA)

INCHI for CFc000002002 (3-Oxooctanoyl-CoA)

Structure for CFc000002002 (3-Oxooctanoyl-CoA)

3D Structure for CFc000002002 (3-Oxooctanoyl-CoA)