ChemFOnt: Showing chemical card for trans,cis-Lauro-2,6-dienoyl-CoA (CFc000006763)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:50 UTC

Chemfont ID

CFc000006763

Molecule Identification

Common Name

trans,cis-Lauro-2,6-dienoyl-CoA

Definition

Trans,cis-Lauro-2,6-dienoyl-CoA is a co-enzyme A intermediate that participates in fatty acid metabolism, especially long chain fatty acid biosynthesis. trans,cis-Lauro-2,6-dienoyl-CoA is converted from cis,cis-3,6-Dodecadienoyl-CoA via the enzyme known as dodecenoyl-CoA delta-isomerase [EC:5.3.3.8] and vice-versa. Fatty acid degradation is the process in which fatty acids are broken down, resulting in release of energy. It includes three major steps: Activation and transport into mitochondria, β-oxidation and movement through the electron transport chain. Fatty acids are transported across the outer mitochondrial membrane by carnitine-palmitoyl transferase I (CPT-I), and then couriered across the inner mitochondrial membrane by carnitine (PMID:11413487 ). Once inside the mitochondrial matrix, fatty acyl-carnitine reacts with coenzyme A to release the fatty acid and produce acetyl-CoA. CPT-I is believed to be the rate limiting step in fatty acid oxidation. Once inside the mitochondrial matrix, fatty acids undergo β-oxidation (PMID: 25703630 ). During this process, two-carbon molecules (in the form of acetyl-CoA) are repeatedly cleaved from the fatty acid. Acetyl-CoA can then enter the TCA cycle, which produces NADH and FADH. NADH and FADH are subsequently used in the electron transport chain to produce ATP, the energy currency of the cell.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₃₃H₅₄N₇O₁₇P₃S

Average Molecular Weight

945.805

Monoisotopic Molecular Weight

945.250973563

IUPAC Name

{[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(dodeca-2,5-dienoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,3R,5R)-5-(6-aminopurin-9-yl)-2-[({[(3R)-3-[(2-{[2-(dodeca-2,5-dienoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxyphosphonic acid

CAS Registry Number

None

SMILES

[H][C@](O)(C(=O)NCCC(=O)NCCSC(=O)C=CCC=CCCCCCC)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@]([H])(C(O)[C@@]1([H])OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C33H54N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-24(42)61-17-16-35-23(41)14-15-36-31(45)28(44)33(2,3)19-54-60(51,52)57-59(49,50)53-18-22-27(56-58(46,47)48)26(43)32(55-22)40-21-39-25-29(34)37-20-38-30(25)40/h9-10,12-13,20-22,26-28,32,43-44H,4-8,11,14-19H2,1-3H3,(H,35,41)(H,36,45)(H,49,50)(H,51,52)(H2,34,37,38)(H2,46,47,48)/t22-,26?,27+,28+,32-/m1/s1

InChI Key

ZSJRXHRCABOSNC-CQGYPEFWSA-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 diphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside 3',5'-bisphosphate
Ribonucleoside 3'-phosphate
Pentose-5-phosphate
Pentose phosphate
N-glycosyl compound
Glycosyl compound
Beta amino acid or derivatives
Pentose monosaccharide
Organic pyrophosphate
Monosaccharide phosphate
6-aminopurine
Purine
Imidazopyrimidine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
Alkyl phosphate
Pyrimidine
Phosphoric acid ester
Organic phosphoric acid derivative
N-substituted imidazole
N-acyl-amine
Monosaccharide
Fatty amide
Heteroaromatic compound
Tetrahydrofuran
Imidazole
Azole
Carbothioic s-ester
Thiocarboxylic acid ester
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Sulfenyl compound
Thiocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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: HMDB0011123)
Membrane (HMDB: HMDB0011123)

Source

Exogenous

Exogenous (HMDB: HMDB0011123)

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: HMDB0011123)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.75 g/L	ALOGPS
logP	1.51	ALOGPS
logP	-2.4	ChemAxon
logS	-2.7	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	28	ChemAxon
Refractivity	220.45 m³·mol⁻¹	ChemAxon
Polarizability	88.95 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

FDB027905

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for trans,cis-Lauro-2,6-dienoyl-CoA (CFc000006763)

MOL for CFc000006763 (trans,cis-Lauro-2,6-dienoyl-CoA)

3D MOL for CFc000006763 (trans,cis-Lauro-2,6-dienoyl-CoA)

3D SDF for CFc000006763 (trans,cis-Lauro-2,6-dienoyl-CoA)

3D-SDF for CFc000006763 (trans,cis-Lauro-2,6-dienoyl-CoA)

PDB for CFc000006763 (trans,cis-Lauro-2,6-dienoyl-CoA)

3D PDB for CFc000006763 (trans,cis-Lauro-2,6-dienoyl-CoA)

SMILES for CFc000006763 (trans,cis-Lauro-2,6-dienoyl-CoA)

INCHI for CFc000006763 (trans,cis-Lauro-2,6-dienoyl-CoA)

Structure for CFc000006763 (trans,cis-Lauro-2,6-dienoyl-CoA)

3D Structure for CFc000006763 (trans,cis-Lauro-2,6-dienoyl-CoA)