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Showing metabocard for 8Z,11Z,14Z-eicosatrienoyl-CoA (HMDB03947)

Record Information
Version 3.5
Creation Date 2006-08-13 01:53:42 -0600
Update Date 2013-05-13 15:39:28 -0600
HMDB ID HMDB03947
Secondary Accession Numbers None
Metabolite Identification
Common Name 8Z,11Z,14Z-eicosatrienoyl-CoA
Description

8Z,11Z,14Z-eicosatrienoyl-CoA participates in the biosynthesis of unsaturated fatty acids. 8Z,11Z,14Z-eicosatrienoyl-CoA is converted from (8Z,11Z,14Z)-Icosatrienoic acid via palmitoyl-CoA hydrolase [EC:3.1.2.2].

Unsaturated fatty acids are of similar form, except that one or more alkenyl functional groups exist along the chain, with each alkene substituting a single-bonded "-CH2-CH2-" part of the chain with a double-bonded "-CH=CH-" portion (that is, a carbon double-bonded to another carbon). The differences in geometry between the various types of unsaturated fatty acids, as well as between saturated and unsaturated fatty acids, play an important role in biological processes, and in the construction of biological structures (such as cell membranes). (Wikipedia)

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Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (8Z,11Z,14Z)-Eicosatrienoyl-CoA
  2. (8Z,11Z,14Z)-Eicosatrienoyl-Coenzyme A
Chemical Formula C44H72N7O17P3S
Average Molecular Weight 1096.065
Monoisotopic Molecular Weight 1095.391824139
IUPAC Name {[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(8Z,11Z,14Z,17Z)-tricosa-8,11,14,17-tetraenoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name [(2R,3R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(8Z,11Z,14Z,17Z)-tricosa-8,11,14,17-tetraenoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxyphosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphospho
CAS Registry Number 28879-98-3
SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
InChI Identifier InChI=1S/C44H72N7O17P3S/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/h8-9,11-12,14-15,17-18,31-33,37-39,43,54-55H,4-7,10,13,16,19-30H2,1-3H3,(H,46,52)(H,47,56)(H,60,61)(H,62,63)(H2,45,48,49)(H2,57,58,59)/b9-8-,12-11-,15-14-,18-17-/t33-,37?,38+,39+,43-/m1/s1
InChI Key VPDGJOHYVQUGHC-PGGIITILSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl CoAs
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Carboxamide Group
  • Carboxylic Thioester
  • Coenzyme A
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purine Ribonucleoside 3',5' Bisphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
Direct Parent Acyl CoAs
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Lipid biosynthesis, Fatty acid transport
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -0.045 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.18 g/L ALOGPS
LogP 4.06 ALOGPS
LogP 1.17 ChemAxon
LogS -3.77 ALOGPS
pKa (strongest acidic) 0.83 ChemAxon
pKa (strongest basic) 4.95 ChemAxon
Hydrogen Acceptor Count 17 ChemAxon
Hydrogen Donor Count 9 ChemAxon
Polar Surface Area 363.63 A2 ChemAxon
Rotatable Bond Count 37 ChemAxon
Refractivity 273.32 ChemAxon
Polarizability 110.37 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023266
KNApSAcK ID Not Available
Chemspider ID 17220835 Link_out
KEGG Compound ID Not Available
BioCyc ID 5Z8Z11Z13E-15S-15-HYDROPEROXYICOS Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB03947 Link_out
Metagene Link HMDB03947 Link_out
METLIN ID Not Available
PubChem Compound 16061156 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Cytosolic acyl coenzyme A thioester hydrolase
Reactions:
    Gene Name: ACOT7
    Uniprot ID: O00154 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Acyl-coenzyme A thioesterase 2, mitochondrial
    Reactions:
      Gene Name: ACOT2
      Uniprot ID: P49753 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA