Crustecdysone (CHEM024206)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:33:41 UTC
Update Date2016-11-09 01:17:51 UTC
Accession NumberCHEM024206
Identification
Common NameCrustecdysone
ClassSmall Molecule
DescriptionAn ecdysteroid that is ecdysone substituted by a hydroxy group at position 20.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
20-OH EcdysoneChEBI
beta-EcdysoneChEBI
beta-EcdysteroneChEBI
EcdysteroneChEBI
b-EcdysoneGenerator
Β-ecdysoneGenerator
b-EcdysteroneGenerator
Β-ecdysteroneGenerator
20 HydroxyecdysoneHMDB
Beta EcdysoneHMDB
CrustecdysoneChEBI
(2beta,3beta,5beta,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-onePhytoBank
(2β,3β,5β,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-onePhytoBank
(+)-20-HydroxyecdysonePhytoBank
(+)-EcdysteronePhytoBank
20-Hydroxy-alpha-ecdysonePhytoBank
20-Hydroxy-α-ecdysonePhytoBank
20-HydroxyecdysonePhytoBank
20R-HydroxyecdysonePhytoBank
2beta,3beta,14alpha,20beta,22alpha,25-Hexahydroxycholest-7-en-6-onePhytoBank
2β,3β,14α,20β,22α,25-Hexahydroxycholest-7-en-6-onePhytoBank
CommisteronePhytoBank
CrustecdysonPhytoBank
EcdystenPhytoBank
EcdysteronPhytoBank
EkdistenPhytoBank
Polypodin APhytoBank
Polypodin CPhytoBank
Polypodine APhytoBank
Polypodine CPhytoBank
beta-EcydisonePhytoBank
β-EcydisonePhytoBank
Chemical FormulaC27H44O7
Average Molecular Mass480.634 g/mol
Monoisotopic Mass480.309 g/mol
CAS Registry Number5289-74-7
IUPAC Name(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one
Traditional Name(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one
SMILESCC(C)(O)CCC(O)C(C)(O)C1CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C
InChI IdentifierInChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3
InChI KeyNKDFYOWSKOHCCO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentHydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Hexahydroxy bile acid, alcohol, or derivatives
  • Cholesterol
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • Ecdysteroid
  • 25-hydroxysteroid
  • Hydroxy bile acid, alcohol, or derivatives
  • 22-hydroxysteroid
  • 20-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • 2-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Oxosteroid
  • 6-oxosteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 14-hydroxysteroid
  • 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 Solubility0.42 g/LALOGPS
logP1.3ALOGPS
logP0.61ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)13.26ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area138.45 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity128.88 m³·mol⁻¹ChemAxon
Polarizability53.6 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0000900000-61270eb4d9884b80e40eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2104900000-692f7d34774f4473eccdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-9126800000-56abcd661a69fa5e2c03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-0000900000-5e5c27b2b419a59ebd72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1208900000-336da290c6badec732ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xv-2119200000-0bf9ed70e7072a4014efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-75b6ff99e4177dc88738Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0002900000-1923d3135a2dc1b8fd6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-2003900000-811d22e2b8b9e164dbcbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ea-0000900000-67d135935e5b3e73f5bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-9601100000-0fde0df3bd89adff2c2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4619000000-7db2496ddb29894962faSpectrum
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 IDHMDB0030180
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00003654
BiGG IDNot Available
BioCyc IDCPD-276
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link20-Hydroxyecdysone
Chemspider ID4573597
ChEBI ID16587
PubChem Compound ID5459840
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15609826
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25593010
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=8748375
4. Kaplanis JN, Thompson MJ, Dutky SR, Robbins WE: The ecdysteroids from the tobacco hornworm during pupal-adult development five days after peak titer of molting hormone activity. Steroids. 1979 Sep;34(3):333-45.
5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
6. 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.
7. 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.
8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
10. The lipid handbook with CD-ROM