ChemFOnt: Showing chemical card for Palmitelaidoyl-CoA (CFc000002073)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:52 UTC

Chemfont ID

CFc000002073

Molecule Identification

Common Name

Palmitelaidoyl-CoA

Definition

Palmitelaidoyl-CoA is a monounsaturated fatty acid, the product of palmitoyl-CoA from a reaction catalyzed by stearoyl-CoA desaturase (EC 1.14.99.5, SCD) in the endoplasmic reticulum, an enzyme that catalyzes the delta9-cis desaturation of saturated fatty acyl-CoAs. These monounsaturated fatty acids are used as substrates for the synthesis of triglycerides, wax esters, cholesteryl esters, and membrane phospholipids. The saturated to monounsaturated fatty acid ratio affects membrane phospholipid composition and alteration in this ratio has been implicated in a variety of disease states including cardiovascular disease, obesity, diabetes, neurological disease, skin disorders, and cancer. Thus, the expression of SCD is of physiological importance in normal and disease states. Unsaturated fatty acids are the most abundant form of stored fat in the human body and are vital for all living organisms. In addition to their role as an energy source, they are integral constituents of cell membranes, playing a role in membrane fluidity, cell signalling, and membrane integrity. Numerous beneficial physiologic effects have been attributed to unsaturated fatty acids, including protection from obesity, diabetes, cancer, and atherosclerosis. Palmitelaidoyl-CoA has been shown to inhibit oxidative phosphorylation in human cells which has implications for long-chain fatty acid disorders (PMID: 12538075 , 16020546 , 16651524 , 7662716 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-S-9-Hexadecenoate	HMDB
(e)-S-9-Hexadecenoate CoA	HMDB
(e)-S-9-Hexadecenoate coenzyme A	HMDB
(e)-S-9-Hexadecenoic acid	HMDB
Palmitelaidylcoenzyme A	HMDB
S-(9E)-9-Hexadecenoate	HMDB
S-(9E)-9-Hexadecenoate CoA	HMDB
S-(9E)-9-Hexadecenoate coenzyme A	HMDB
S-(9E)-9-Hexadecenoic acid	HMDB
trans-9-Hexadecenoylcoenzyme A	HMDB

Chemical Formula

C₃₇H₆₄N₇O₁₇P₃S

Average Molecular Weight

1003.927

Monoisotopic Molecular Weight

1003.329223883

IUPAC Name

4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-[2-({2-[(9E)-hexadec-9-enoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidic acid

Traditional Name

4-[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-N-[2-({2-[(9E)-hexadec-9-enoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidic acid

CAS Registry Number

62358-02-5

SMILES

[H]\C(CCCCCC)=C(\[H])CCCCCCCC(=O)SCCN=C(O)CCN=C(O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12

InChI Identifier

InChI=1S/C37H64N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h9-10,24-26,30-32,36,47-48H,4-8,11-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/b10-9+

InChI Key

QBYOCCWNZAOZTL-MDZDMXLPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a 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 fatty 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
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

Extracellular (HMDB: HMDB0004149)
Membrane (HMDB: HMDB0004149)

Source

Exogenous

Exogenous (HMDB: HMDB0004149)

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: HMDB0004149)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.54 g/L	ALOGPS
logP	2.65	ALOGPS
logP	0.5	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	6.43	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	33	ChemAxon
Refractivity	238.81 m³·mol⁻¹	ChemAxon
Polarizability	99.52 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

FDB023962

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

6115728

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Studies on long chain cis- and trans-acyl-CoA esters and acyl-CoA dehydrogenase from rat heart mitochondria. Korsrud, G. O.; Conacher, H. B. S.; Jarvis, G. A.; Beare-Rogers, J. L. Health Prot. Branch, Health Welfare Canada, Ottawa, ON, Can.

Showing chemical card for Palmitelaidoyl-CoA (CFc000002073)

MOL for CFc000002073 (Palmitelaidoyl-CoA)

3D MOL for CFc000002073 (Palmitelaidoyl-CoA)

3D SDF for CFc000002073 (Palmitelaidoyl-CoA)

3D-SDF for CFc000002073 (Palmitelaidoyl-CoA)

PDB for CFc000002073 (Palmitelaidoyl-CoA)

3D PDB for CFc000002073 (Palmitelaidoyl-CoA)

SMILES for CFc000002073 (Palmitelaidoyl-CoA)

INCHI for CFc000002073 (Palmitelaidoyl-CoA)

Structure for CFc000002073 (Palmitelaidoyl-CoA)

3D Structure for CFc000002073 (Palmitelaidoyl-CoA)