12alpha-Hydroxy-13,18-dehydroparain (CHEM032884)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:46:17 UTC
Update Date2016-11-09 01:20:48 UTC
Accession NumberCHEM032884
Identification
Common Name12alpha-Hydroxy-13,18-dehydroparain
ClassSmall Molecule
Description12alpha-Hydroxy-13,18-dehydroparain is a constituent of Quassia amara (Surinam quassia).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
12a-Hydroxy-13,18-dehydroparainGenerator
12Α-hydroxy-13,18-dehydroparainGenerator
12a-Hydroxy-13,18-dehyroparainHMDB
Chemical FormulaC21H28O6
Average Molecular Mass376.443 g/mol
Monoisotopic Mass376.189 g/mol
CAS Registry NumberNot Available
IUPAC Name15,16-dihydroxy-4-methoxy-2,6,17-trimethyl-14-methylidene-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-ene-3,11-dione
Traditional Name15,16-dihydroxy-4-methoxy-2,6,17-trimethyl-14-methylidene-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-ene-3,11-dione
SMILESCOC1=CC(C)C2CC3OC(=O)CC4C(=C)C(O)C(O)C(C34C)C2(C)C1=O
InChI IdentifierInChI=1S/C21H28O6/c1-9-6-13(26-5)19(25)21(4)11(9)7-14-20(3)12(8-15(22)27-14)10(2)16(23)17(24)18(20)21/h6,9,11-12,14,16-18,23-24H,2,7-8H2,1,3-5H3
InChI KeyCKRHSGZMMGXRKZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentQuassinoids
Alternative Parents
Substituents
  • C-20 quassinoid skeleton
  • Quassinoid
  • Naphthopyran
  • Naphthalene
  • Delta valerolactone
  • Delta_valerolactone
  • Cyclohexenone
  • Oxane
  • Pyran
  • Cyclic alcohol
  • Lactone
  • Ketone
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility1.43 g/LALOGPS
logP1.01ALOGPS
logP1.03ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)13.41ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity98.57 m³·mol⁻¹ChemAxon
Polarizability39.19 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-1219000000-553731e4c541d2274bbfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a6r-5501950000-f8b9dbd0ecf42321e684Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0019000000-f5ed17c486dacc3a2ad4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0691-0029000000-013f896fed10cebcc930Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9743000000-fc765d08ddfbda7e1551Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-e25e3b2edd7a6f58ad2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-0009000000-ce4e42cb61a82b572d3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-4119000000-752413c0e95a1fe26fb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-c368f44a479308dabd96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00mn-0039000000-e278d7439c74db7a2720Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ti-2896000000-14dfea04b01bc7454b26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-5787d9cbf10c62f3d8eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0009000000-794e4923c6d4fede4f9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avm-1029000000-7f026e748ebbd6613469Spectrum
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 IDHMDB0039557
FooDB IDFDB019178
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014820
ChEBI ID175842
PubChem Compound ID73081379
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM