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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-02-24 01:29:45 UTC
Update Date2023-02-21 17:30:41 UTC
HMDB IDHMDB0062202
Secondary Accession Numbers
  • HMDB62202
Metabolite Identification
Common Name(3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoA
Description(3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoA, also known as 3(S)-hydroxy-all-cis-8,11,14,17-eicosatetraenoyl-CoA, 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. (3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoA is considered to be a practically insoluble (in water) and relatively neutral molecule.
Structure
Data?1677000641
Synonyms
ValueSource
(3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoAHMDB
(3S,8Z,11Z,14Z,17Z)-3-Hydroxyeicosatetraenoyl-CoAGenerator, HMDB
(3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetra-8,11,14,17-enoyl-CoAHMDB
(3S,8Z,11Z,14Z,17Z)-3-Hydroxyeicosatetra-8,11,14,17-enoyl-CoAGenerator, HMDB
3S-Hydroxyicosatetra-8Z,11Z,14Z,17Z-enoyl-CoAHMDB
3S-Hydroxyeicosatetra-8Z,11Z,14Z,17Z-enoyl-CoAGenerator, HMDB
3(S)-Hydroxy-all-cis-8,11,14,17-icosatetraenoyl-CoAHMDB
3(S)-Hydroxy-all-cis-8,11,14,17-eicosatetraenoyl-CoAGenerator, HMDB
(3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-coenzyme AGenerator, HMDB
(3S,8Z,11Z,14Z,17Z)-3-Hydroxyeicosatetraenoyl-coenzyme AGenerator, HMDB
(3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetra-8,11,14,17-enoyl-coenzyme AGenerator, HMDB
(3S,8Z,11Z,14Z,17Z)-3-Hydroxyeicosatetra-8,11,14,17-enoyl-coenzyme AGenerator, HMDB
3S-Hydroxyicosatetra-8Z,11Z,14Z,17Z-enoyl-coenzyme AGenerator, HMDB
3S-Hydroxyeicosatetra-8Z,11Z,14Z,17Z-enoyl-coenzyme AGenerator, HMDB
3(S)-Hydroxy-all-cis-8,11,14,17-icosatetraenoyl-coenzyme AGenerator, HMDB
3(S)-Hydroxy-all-cis-8,11,14,17-eicosatetraenoyl-coenzyme AGenerator, HMDB
Chemical FormulaC41H66N7O18P3S
Average Molecular Weight1069.99
Monoisotopic Molecular Weight1069.339790481
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-({2-[(2-{[(3S,8Z,11Z,14Z,17Z)-3-hydroxyicosa-8,11,14,17-tetraenoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]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((3R)-3-hydroxy-3-({2-[(2-{[(3S,8Z,11Z,14Z,17Z)-3-hydroxyicosa-8,11,14,17-tetraenoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/CCCC[C@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](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/C41H66N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-29(49)24-32(51)70-23-22-43-31(50)20-21-44-39(54)36(53)41(2,3)26-63-69(60,61)66-68(58,59)62-25-30-35(65-67(55,56)57)34(52)40(64-30)48-28-47-33-37(42)45-27-46-38(33)48/h5-6,8-9,11-12,14-15,27-30,34-36,40,49,52-53H,4,7,10,13,16-26H2,1-3H3,(H,43,50)(H,44,54)(H,58,59)(H,60,61)(H2,42,45,46)(H2,55,56,57)/b6-5-,9-8-,12-11-,15-14-/t29-,30+,34+,35+,36-,40+/m0/s1
InChI KeyPCGPHLMAAZKQFQ-LXHLOETDSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.67ALOGPS
logP-0.3ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area383.86 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity261.03 m³·mol⁻¹ChemAxon
Polarizability104.2 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+H]+276.93830932474
DeepCCS[M-H]-274.06930932474
DeepCCS[M-2H]-311.35730932474
DeepCCS[M+Na]+285.59530932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoA 10V, Positive-QTOFsplash10-000i-5901120200-3e789e10129748e852b22019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoA 20V, Positive-QTOFsplash10-000i-0913140000-fd9f88cc8744d80958ec2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoA 40V, Positive-QTOFsplash10-000i-1900010000-95034291253f0735ba342019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoA 10V, Negative-QTOFsplash10-0ge9-9633240510-5c3c819471aa2c8ba75f2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoA 20V, Negative-QTOFsplash10-001i-5911310100-d6677bbb46fbdc90c08e2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoA 40V, Negative-QTOFsplash10-057i-5900100000-4c5047b0439deb8dc9f62019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoA 10V, Negative-QTOFsplash10-014i-9000000000-d7c2f9b69fdd5b1c12e12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoA 20V, Negative-QTOFsplash10-0ldi-9200101230-4d88e70eb3440cc3a0652021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoA 40V, Negative-QTOFsplash10-00or-9201301402-8170982294d244dc45e62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoA 10V, Positive-QTOFsplash10-0fk9-9100000001-cf0c0f8ff7590326230f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoA 20V, Positive-QTOFsplash10-001r-9500000033-b7f550d14e24d7defbb32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3S,8Z,11Z,14Z,17Z)-3-Hydroxyicosatetraenoyl-CoA 40V, Positive-QTOFsplash10-03di-0200490000-e300b658c67a30b4c5322021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 CompoundNot Available
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 ReferencesNot Available