Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 03:12:12 UTC
Update Date2022-03-07 03:17:56 UTC
HMDB IDHMDB0062537
Secondary Accession Numbers
  • HMDB62537
Metabolite Identification
Common NameTricosanoyl-CoA
DescriptionTricosanoyl-coa, also known as C23-CoA(4-) or tricosanoyl-coenzyme A(4-) is an acyl-CoA or acyl-coenzyme A. More specifically, it is a tricosanoic acid thioester of coenzyme A. Tricosanoyl-coa is an acyl-CoA with 23 fatty acid group as the acyl moiety attached to coenzyme A. Coenzyme A was discovered in 1946 by Fritz Lipmann (Journal of Biological Chemistry (1946) 162 (3): 743–744) and its structure was determined in the early 1950s at the Lister Institute in London. Coenzyme A is a complex, thiol-containing molecule that is naturally synthesized from pantothenate (vitamin B5), which is found in various foods such as meat, vegetables, cereal grains, legumes, eggs, and milk. More specifically, coenzyme A (CoASH or CoA) consists of a beta-mercaptoethylamine group linked to the vitamin pantothenic acid (B5) through an amide linkage and 3'-phosphorylated ADP. Coenzyme A is synthesized in a five-step process that requires four molecules of ATP, pantothenate and cysteine. It is believed that there are more than 1100 types of acyl-CoA’s in the human body, which also corresponds to the number of acylcarnitines in the human body. Acyl-CoAs exists in all living species, ranging from bacteria to plants to humans. The general role of acyl-CoA’s is to assist in transferring fatty acids from the cytoplasm to mitochondria. This process facilitates the production of fatty acids in cells, which are essential in cell membrane structure. Acyl-CoA's are also susceptible to beta oxidation, forming, ultimately, acetyl-CoA. Acetyl-CoA can enter the citric acid cycle, eventually forming several equivalents of ATP. In this way, fats are converted to ATP -- or biochemical energy. Acyl-CoAs can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain acyl-CoAs; 2) medium-chain acyl-CoAs; 3) long-chain acyl-CoAs; and 4) very long-chain acyl-CoAs; 5) hydroxy acyl-CoAs; 6) branched chain acyl-CoAs; 7) unsaturated acyl-CoAs; 8) dicarboxylic acyl-CoAs and 9) miscellaneous acyl-CoAs. Short-chain acyl-CoAs have acyl-groups with two to four carbons (C2-C4), medium-chain acyl-CoAs have acyl-groups with five to eleven carbons (C5-C11), long-chain acyl-CoAs have acyl-groups with twelve to twenty carbons (C12-C20) while very long-chain acyl-CoAs have acyl groups with more than 20 carbons. Tricosanoyl-coa is therefore classified as a very long chain acyl-CoA. The oxidative degradation of fatty acids is a two-step process, catalyzed by acyl-CoA synthetase/synthase. Fatty acids are first converted to their acyl phosphate, the precursor to acyl-CoA. The latter conversion is mediated by acyl-CoA synthase. Three types of acyl-CoA synthases are employed, depending on the chain length of the fatty acid. Tricosanoyl-coa, being a very long chain acyl-CoA is a substrate for very long chain acyl-CoA synthase. The second step of fatty acid degradation is beta oxidation. Beta oxidation occurs in mitochondria and, in the case of very long chain acyl-CoAs, the peroxisome. After its formation in the cytosol, Tricosanoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of Tricosanoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts Tricosanoyl-CoA into Tricosanoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, Tricosanoylcarnitine is converted back to Tricosanoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of Tricosanoyl-CoA occurs in four steps. First, since Tricosanoyl-CoA is a very long chain acyl-CoA it is the substrate for a very long chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of Tricosanoyl-CoA, creating a double bond between the alpha and beta carbons. FAD is the hydrogen acceptor, yielding FADH2. Second, Enoyl-CoA hydrase catalyzes the addition of water across the newly formed double bond to make an alcohol. Third, 3-hydroxyacyl-CoA dehydrogenase oxidizes the alcohol group to a ketone and NADH is produced from NAD+. Finally, Thiolase cleaves between the alpha carbon and ketone to release one molecule of acetyl-CoA and a new acyl-CoA which is now 2 carbons shorter. This four-step process repeats until Tricosanoyl-CoA has had all its carbons removed from the chain, leaving only acetyl-CoA. Beta oxidation, as well as alpha-oxidation, also occurs in the peroxisome. The peroxisome handles beta oxidation of fatty acids that have more than 20 carbons in their chain because the peroxisome contains very-long-chain Acyl-CoA synthetases and dehydrogenases. The heart primarily metabolizes fat for energy and Acyl-CoA metabolism has been identified as a critical molecule in early-stage heart muscle pump failure. Cellular acyl-CoA content also correlates with insulin resistance, suggesting that it can mediate lipotoxicity in non-adipose tissues. Acyl-CoA: diacylglycerol acyltransferase (DGAT) plays an important role in energy metabolism on account of key enzyme in triglyceride biosynthesis. The study of acyl-CoAs is an active area of research and it is likely that many novel acyl-CoAs will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered for these molecules.
Structure
Data?1563866326
Synonyms
ValueSource
4-({[({[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-(tricosanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidateGenerator
4-({[({[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-(tricosanoylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidateGenerator
4-({[({[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-(tricosanoylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acidGenerator
C23-CoA(4-)HMDB
Tricosanoyl-coenzyme A(4-)HMDB
Chemical FormulaC44H80N7O17P3S
Average Molecular Weight1104.14
Monoisotopic Molecular Weight1103.454426312
IUPAC Name4-({[({[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-(tricosanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid
Traditional Name4-[({[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-(tricosanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCCC(=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/C44H80N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-35(53)72-28-27-46-34(52)25-26-47-42(56)39(55)44(2,3)30-65-71(62,63)68-70(60,61)64-29-33-38(67-69(57,58)59)37(54)43(66-33)51-32-50-36-40(45)48-31-49-41(36)51/h31-33,37-39,43,54-55H,4-30H2,1-3H3,(H,46,52)(H,47,56)(H,60,61)(H,62,63)(H2,45,48,49)(H2,57,58,59)
InChI KeyGBAQBZWAXMYXRJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as very long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentVery long-chain fatty acyl 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
  • 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
  • Monosaccharide
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Carbothioic s-ester
  • Thiocarboxylic acid ester
  • Secondary alcohol
  • Amino acid or derivatives
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • 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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.03 g/lALOGPS
LogP4.74ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP4.39ALOGPS
logP3.97ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)6.43ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area370.61 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity269.9 m³·mol⁻¹ChemAxon
Polarizability115.82 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-301.71130932474
DeepCCS[M+Na]+275.48730932474
AllCCS[M+H]+314.132859911
AllCCS[M+H-H2O]+314.632859911
AllCCS[M+NH4]+313.632859911
AllCCS[M+Na]+313.532859911
AllCCS[M-H]-297.932859911
AllCCS[M+Na-2H]-303.432859911
AllCCS[M+HCOO]-309.332859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoyl-CoA 10V, Positive-QTOFsplash10-000i-4801910200-9c8c1ff733ef80ae11b12019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoyl-CoA 20V, Positive-QTOFsplash10-01p9-1902820000-54bd0581817213f99b732019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoyl-CoA 40V, Positive-QTOFsplash10-000i-2900400000-c3126313ca86ef600b212019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoyl-CoA 10V, Negative-QTOFsplash10-001r-5904141400-9b570bd9d9b1e55e85f22019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoyl-CoA 20V, Negative-QTOFsplash10-001i-4901120100-df35c3b6ce45e1d505422019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoyl-CoA 40V, Negative-QTOFsplash10-057i-5900000000-765e0cde68126b7cd1942019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoyl-CoA 10V, Positive-QTOFsplash10-0udi-0900000000-1b618dfa905a1a66694a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoyl-CoA 20V, Positive-QTOFsplash10-0fvr-9100100413-a87ed07d3cebdea7c8802021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoyl-CoA 40V, Positive-QTOFsplash10-0002-0000290000-f7f88d316e671414e4de2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoyl-CoA 10V, Negative-QTOFsplash10-0udi-0900000000-3a90f84ce9673f1af6df2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoyl-CoA 20V, Negative-QTOFsplash10-0ufr-7902305310-ddaf62e5b2854f75c82b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoyl-CoA 40V, Negative-QTOFsplash10-004i-9102300100-76332bd3acd3ab4353a12021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound75250440
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.