ChemFOnt: Showing chemical card for Undecanoyl-CoA (CFc000008204)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:52 UTC

Chemfont ID

CFc000008204

Molecule Identification

Common Name

Undecanoyl-CoA

Definition

Undecanoyl CoA is an acyl-CoA with the C-11 Acyl chain. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid, inside living cells. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. This is then used in the citric acid cycle to start a chain of reactions, eventually forming many adenosine triphosphates. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. First, the fatty acid displaces the diphosphate group of ATP, then coenzyme A (HSCoA) displaces the AMP group to form an Acyl-CoA. The acyladenylate product of the first step has a large free energy of hydrolysis and conserves the free energy of the cleaved phosphoanhydride bond in ATP. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Consequently, the overall reaction Fatty acid + CoA + ATP <=> Acyl-CoA + AMP + PPi has a free energy change near zero. Subsequent hydrolysis of the product PPi (by the enzyme inorganic pyrophosphatase) is highly exergonic, and this reaction makes the formation of acyl-CoA spontaneous and irreversible. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. Because there is no transport protein for CoA adducts, acyl groups must enter the mitochondria via a shuttle system involving the small molecule carnitine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Methyloctanoyl CoA, 21	HMDB
2-Methyloctanoyl coenzyme A, 21	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-(undecanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidate	Generator
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-(undecanoylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidate	Generator
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-(undecanoylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid	Generator

Chemical Formula

C₃₂H₅₆N₇O₁₇P₃S

Average Molecular Weight

935.81

Monoisotopic Molecular Weight

935.266623627

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-(undecanoylsulfanyl)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-(undecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

None

SMILES

CCCCCCCCCCC(=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/C32H56N7O17P3S/c1-4-5-6-7-8-9-10-11-12-23(41)60-16-15-34-22(40)13-14-35-30(44)27(43)32(2,3)18-53-59(50,51)56-58(48,49)52-17-21-26(55-57(45,46)47)25(42)31(54-21)39-20-38-24-28(33)36-19-37-29(24)39/h19-21,25-27,31,42-43H,4-18H2,1-3H3,(H,34,40)(H,35,44)(H,48,49)(H,50,51)(H2,33,36,37)(H2,45,46,47)/t21-,25-,26-,27?,31-/m1/s1

InChI Key

IZWCGXGZGYKDHR-WMMBNDHFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

2,3,4-saturated 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

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0013114)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013114)

Source

Endogenous

Endogenous (HMDB: HMDB0013114)

Animal

Animal (HMDB: HMDB0013114)

Exogenous

Food

Food (HMDB: HMDB0013114)

Exogenous (HMDB: HMDB0013114)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0013114)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0013114)

Lipid metabolism pathway (HMDB: HMDB0013114)

Cellular process

Cell signaling (HMDB: HMDB0013114)

Biochemical process

Lipid transport (HMDB: HMDB0013114)

Role

Biological role

Energy source (HMDB: HMDB0013114)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013114)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.84 g/L	ALOGPS
logP	1.12	ALOGPS
logP	-1.6	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	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	29	ChemAxon
Refractivity	213.64 m³·mol⁻¹	ChemAxon
Polarizability	89.35 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

HMDB0013114

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029290

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

53481608

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Undecanoyl-CoA (CFc000008204)

MOL for CFc000008204 (Undecanoyl-CoA)

3D MOL for CFc000008204 (Undecanoyl-CoA)

3D SDF for CFc000008204 (Undecanoyl-CoA)

3D-SDF for CFc000008204 (Undecanoyl-CoA)

PDB for CFc000008204 (Undecanoyl-CoA)

3D PDB for CFc000008204 (Undecanoyl-CoA)

SMILES for CFc000008204 (Undecanoyl-CoA)

INCHI for CFc000008204 (Undecanoyl-CoA)

Structure for CFc000008204 (Undecanoyl-CoA)

3D Structure for CFc000008204 (Undecanoyl-CoA)