ChemFOnt: Showing chemical card for 3-Oxooctadecanoyl-CoA (CFc000002773)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:44 UTC

Chemfont ID

CFc000002773

Molecule Identification

Common Name

3-Oxooctadecanoyl-CoA

Definition

3-Oxooctadecanoyl-CoA is a metabolite intermediate in the microsomal fatty acid chain elongation system. Microsomal electron-transport components NADPH-cytochrome P450 reductase (EC 1.6.2.4) and cytochrome b5 (EC 1.6.2.2) participate in the conversion from 3-Oxooctadecanoyl-CoA to beta-hydroxystearoyl-CoA, the first reductive step of the microsomal chain elongating system initiated by NADPH. (PMID: 6404652 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Ketostearoyl-CoA	HMDB
3-Ketostearoyl-coenzyme A	HMDB
3-Oxostearoyl-CoA	HMDB
3-Oxostearoyl-coenzyme A	HMDB
beta-Ketostearoyl-CoA	HMDB
beta-Ketostearoyl-coenzyme A	HMDB

Chemical Formula

C₃₉H₆₆N₇O₁₈P₃S

Average Molecular Weight

1045.964

Monoisotopic Molecular Weight

1045.339788569

IUPAC Name

(2R)-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-[(3-oxooctadecanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanecarboximidate

Traditional Name

(2R)-4-[({[(2R,3S,4R,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-[(3-oxooctadecanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanecarboximidate

CAS Registry Number

86370-20-9

SMILES

[H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)CC(=O)CCCCCCCCCCCCCCC)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)[C@]1([H])OP(O)(O)=O

InChI Identifier

InChI=1S/C39H68N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(47)22-30(49)68-21-20-41-29(48)18-19-42-37(52)34(51)39(2,3)24-61-67(58,59)64-66(56,57)60-23-28-33(63-65(53,54)55)32(50)38(62-28)46-26-45-31-35(40)43-25-44-36(31)46/h25-26,28,32-34,38,50-51H,4-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55)/p-2/t28-,32-,33-,34+,38-/m1/s1

InChI Key

LGOGWHDPDVAUNY-LFZQUHGESA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated long aliphatic chain of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Long-chain 3-oxoacyl 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
Alkyl phosphate
1,3-dicarbonyl compound
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Ketone
Thiocarboxylic acid ester
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organopnictogen compound
Hydrocarbon derivative
Organic oxygen compound
Primary amine
Carbonyl group
Organic nitrogen compound
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Organic anion
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: HMDB0006498)

Extracellular (HMDB: HMDB0006498)
Membrane (HMDB: HMDB0006498)

Source

Exogenous

Exogenous (HMDB: HMDB0006498)

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: HMDB0006498)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids (PathBank: SMP0087267)
Fatty Acid Oxidation (Steareate) (PathBank: SMP0121353)
Biosynthesis of Unsaturated Fatty Acids (PathBank: SMP0002324)
Biosynthesis of Unsaturated Fatty Acids (Tetracosanoyl-CoA) (PathBank: SMP0002325)
Biosynthesis of Unsaturated Fatty Acids (Docosanoyl-CoA) (PathBank: SMP0002329)
Biosynthesis of Unsaturated Fatty Acids (Icosanoyl-CoA) (PathBank: SMP0002346)
Biosynthesis of Unsaturated Fatty Acids (Stearoyl-CoA) (PathBank: SMP0002347)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.51 g/L	ALOGPS
logP	3.27	ALOGPS
logP	2.45	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.16	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	393.34 Å²	ChemAxon
Rotatable Bond Count	36	ChemAxon
Refractivity	268.69 m³·mol⁻¹	ChemAxon
Polarizability	104.03 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

FDB023942

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

22833663

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-Oxooctadecanoyl-CoA (CFc000002773)

MOL for CFc000002773 (3-Oxooctadecanoyl-CoA)

3D MOL for CFc000002773 (3-Oxooctadecanoyl-CoA)

3D SDF for CFc000002773 (3-Oxooctadecanoyl-CoA)

3D-SDF for CFc000002773 (3-Oxooctadecanoyl-CoA)

PDB for CFc000002773 (3-Oxooctadecanoyl-CoA)

3D PDB for CFc000002773 (3-Oxooctadecanoyl-CoA)

SMILES for CFc000002773 (3-Oxooctadecanoyl-CoA)

INCHI for CFc000002773 (3-Oxooctadecanoyl-CoA)

Structure for CFc000002773 (3-Oxooctadecanoyl-CoA)

3D Structure for CFc000002773 (3-Oxooctadecanoyl-CoA)