Ecdysone (CHEM026319)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:55:20 UTC
Update Date2016-11-09 01:18:15 UTC
Accession NumberCHEM026319
Identification
Common NameEcdysone
ClassSmall Molecule
DescriptionA 6-oxo steroid that is 5beta-cholest-7-en-6-one substituted by hydroxy groups at positions 2, 3, 14, 22 and 25 respectively (the 2beta, 3beta, 22R stereoisomer). It is a steroid prohormone of the major insect moulting hormone 20-hydroxyecdysone.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(22R)-2beta,3beta,14,22,25-Pentahydroxy-5beta-cholest-7-en-6-oneChEBI
(22R)-2beta,3beta,14alpha,22,25-Pentahydroxy-5beta-cholest-7-en-6-oneChEBI
(22R)-2b,3b,14,22,25-Pentahydroxy-5b-cholest-7-en-6-oneGenerator
(22R)-2Β,3β,14,22,25-pentahydroxy-5β-cholest-7-en-6-oneGenerator
(22R)-2b,3b,14a,22,25-Pentahydroxy-5b-cholest-7-en-6-oneGenerator
(22R)-2Β,3β,14α,22,25-pentahydroxy-5β-cholest-7-en-6-oneGenerator
Molting hormoneMeSH
Chemical FormulaC27H44O6
Average Molecular Mass464.635 g/mol
Monoisotopic Mass464.314 g/mol
CAS Registry NumberNot Available
IUPAC Name(1R,2R,4S,5R,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one
Traditional Name(1R,2R,4S,5R,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one
SMILESC[C@H]([C@H](O)CCC(C)(C)O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C
InChI IdentifierInChI=1S/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,22+,23-,25+,26+,27+/m0/s1
InChI KeyUPEZCKBFRMILAV-JMZLNJERSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentPentahydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Pentahydroxy bile acid, alcohol, or derivatives
  • Cholesterol-skeleton
  • Cholesterol
  • Cholestane-skeleton
  • 25-hydroxysteroid
  • Ecdysteroid
  • 22-hydroxysteroid
  • 14-hydroxysteroid
  • 6-oxosteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 2-hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • Delta-7-steroid
  • Cyclohexenone
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP1.96ALOGPS
logP1.69ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)13.51ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity127.42 m³·mol⁻¹ChemAxon
Polarizability52.93 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0001900000-3fc22d82269db6bf63b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0204900000-7f5cfefde6160b9090b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5329500000-cd2ad6c11bca386db234Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-0000900000-0eae1d10c0ef88f5a770Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0001900000-aae15501ba4e631b82fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-2009500000-dac976c4083b1f3946b8Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDFDB007162
Phenol Explorer IDNot Available
KNApSAcK IDC00003651
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEcdysone
Chemspider IDNot Available
ChEBI ID16688
PubChem Compound ID19212
Kegg Compound IDC00477
YMDB IDNot Available
ECMDB IDM2MDB005434
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19342482
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22310011
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22828514
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23017214
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23072462