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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:36:55 UTC
Update Date2022-03-07 02:54:13 UTC
HMDB IDHMDB0034712
Secondary Accession Numbers
  • HMDB34712
Metabolite Identification
Common NamePrexanthoperol
DescriptionPrexanthoperol, also known as hypargenin C, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review a small amount of articles have been published on Prexanthoperol.
Structure
Data?1563862608
Synonyms
ValueSource
Hypargenin CHMDB
Chemical FormulaC20H26O3
Average Molecular Weight314.4186
Monoisotopic Molecular Weight314.188194698
IUPAC Name6-hydroxy-1,1,4a-trimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-9,10-dione
Traditional Name6-hydroxy-7-isopropyl-1,1,4a-trimethyl-2,3,4,10a-tetrahydrophenanthrene-9,10-dione
CAS Registry Number119817-27-5
SMILES
CC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1C(=O)C2=O
InChI Identifier
InChI=1S/C20H26O3/c1-11(2)12-9-13-14(10-15(12)21)20(5)8-6-7-19(3,4)18(20)17(23)16(13)22/h9-11,18,21H,6-8H2,1-5H3
InChI KeyKVTOPOITUALWOF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Abietane diterpenoid
  • Diterpenoid
  • Hydrophenanthrene
  • Phenanthrene
  • Naphthoquinone
  • Tetralin
  • Naphthalene
  • Aryl ketone
  • Quinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Ketone
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point207 - 210 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.37 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0071 g/LALOGPS
logP4.94ALOGPS
logP5.21ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)7.97ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity91.27 m³·mol⁻¹ChemAxon
Polarizability35.92 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.11731661259
DarkChem[M-H]-173.22231661259
DeepCCS[M+H]+184.31730932474
DeepCCS[M-H]-181.95930932474
DeepCCS[M-2H]-215.80430932474
DeepCCS[M+Na]+191.05130932474
AllCCS[M+H]+174.332859911
AllCCS[M+H-H2O]+171.232859911
AllCCS[M+NH4]+177.232859911
AllCCS[M+Na]+178.032859911
AllCCS[M-H]-185.432859911
AllCCS[M+Na-2H]-185.632859911
AllCCS[M+HCOO]-186.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PrexanthoperolCC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1C(=O)C2=O3336.8Standard polar33892256
PrexanthoperolCC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1C(=O)C2=O2243.8Standard non polar33892256
PrexanthoperolCC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1C(=O)C2=O2677.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prexanthoperol,1TMS,isomer #1CC(C)C1=CC2=C(C=C1O[Si](C)(C)C)C1(C)CCCC(C)(C)C1C(=O)C2=O2761.2Semi standard non polar33892256
Prexanthoperol,1TMS,isomer #2CC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1=C(O[Si](C)(C)C)C2=O2536.8Semi standard non polar33892256
Prexanthoperol,2TMS,isomer #1CC(C)C1=CC2=C(C=C1O[Si](C)(C)C)C1(C)CCCC(C)(C)C1=C(O[Si](C)(C)C)C2=O2548.1Semi standard non polar33892256
Prexanthoperol,2TMS,isomer #1CC(C)C1=CC2=C(C=C1O[Si](C)(C)C)C1(C)CCCC(C)(C)C1=C(O[Si](C)(C)C)C2=O2622.8Standard non polar33892256
Prexanthoperol,1TBDMS,isomer #1CC(C)C1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1(C)CCCC(C)(C)C1C(=O)C2=O3006.9Semi standard non polar33892256
Prexanthoperol,1TBDMS,isomer #2CC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1=C(O[Si](C)(C)C(C)(C)C)C2=O2797.1Semi standard non polar33892256
Prexanthoperol,2TBDMS,isomer #1CC(C)C1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1(C)CCCC(C)(C)C1=C(O[Si](C)(C)C(C)(C)C)C2=O3041.5Semi standard non polar33892256
Prexanthoperol,2TBDMS,isomer #1CC(C)C1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1(C)CCCC(C)(C)C1=C(O[Si](C)(C)C(C)(C)C)C2=O3067.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prexanthoperol GC-MS (Non-derivatized) - 70eV, Positivesplash10-007a-0090000000-0b253e86d44ef0ed09272017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prexanthoperol GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-1109000000-76840f44ea0c7a63eeff2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prexanthoperol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prexanthoperol 10V, Positive-QTOFsplash10-014i-0139000000-640d61d83cc6802d76722015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prexanthoperol 20V, Positive-QTOFsplash10-01bj-3693000000-b985e9188166b85692f42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prexanthoperol 40V, Positive-QTOFsplash10-053r-9430000000-e0135fb1809b28d5ee1d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prexanthoperol 10V, Negative-QTOFsplash10-03di-0009000000-56338b9e1239fbd4e7472015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prexanthoperol 20V, Negative-QTOFsplash10-03di-0019000000-d8c509515cabc261668d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prexanthoperol 40V, Negative-QTOFsplash10-007k-0290000000-51f7c6f24a20330b92be2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prexanthoperol 10V, Positive-QTOFsplash10-014i-0019000000-ba52484b43f69f04c1572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prexanthoperol 20V, Positive-QTOFsplash10-0301-0397000000-76e460d522861191debe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prexanthoperol 40V, Positive-QTOFsplash10-00l5-5390000000-7d32c559a5b54f2bacca2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prexanthoperol 10V, Negative-QTOFsplash10-03di-0009000000-d8638daf32922c2274642021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prexanthoperol 20V, Negative-QTOFsplash10-03di-0029000000-63018d1441af1a82bc6d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prexanthoperol 40V, Negative-QTOFsplash10-0002-0190000000-7a39c02614b86257a6c42021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB014424
KNApSAcK IDC00056609
Chemspider ID546062
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound628742
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1845321
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.