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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:52:23 UTC
Update Date2022-03-07 02:55:01 UTC
HMDB IDHMDB0036706
Secondary Accession Numbers
  • HMDB36706
Metabolite Identification
Common NameSteviol
DescriptionSteviol belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Based on a literature review a significant number of articles have been published on Steviol.
Structure
Data?1563862912
Synonyms
ValueSource
(-)-SteviolHMDB
13-Hydroxy-kaur-16-en-18-Oic acidHMDB
Hydroxydehydrostevic acidHMDB
13-Hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylateGenerator
Steviol, (+,-)-isomerMeSH
Steviol, 3H-labeledMeSH
SteviolMeSH
Chemical FormulaC20H30O3
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
IUPAC Name13-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid
Traditional Namesteviol
CAS Registry Number471-80-7
SMILES
CC12CCCC(C)(C1CCC13CC(=C)C(O)(C1)CCC23)C(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-13-11-19-9-5-14-17(2,7-4-8-18(14,3)16(21)22)15(19)6-10-20(13,23)12-19/h14-15,23H,1,4-12H2,2-3H3,(H,21,22)
InChI KeyQFVOYBUQQBFCRH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentKaurane diterpenoids
Alternative Parents
Substituents
  • Kaurane diterpenoid
  • Tertiary alcohol
  • Cyclic alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point215 °CNot Available
Boiling Point464.00 to 465.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility4.36 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.035 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP3.18ALOGPS
logP3.65ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.7ChemAxon
pKa (Strongest Basic)-0.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity88.89 m³·mol⁻¹ChemAxon
Polarizability36.34 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+174.28431661259
DarkChem[M-H]-168.67331661259
DeepCCS[M-2H]-208.6530932474
DeepCCS[M+Na]+184.21530932474
AllCCS[M+H]+179.832859911
AllCCS[M+H-H2O]+177.032859911
AllCCS[M+NH4]+182.532859911
AllCCS[M+Na]+183.232859911
AllCCS[M-H]-184.132859911
AllCCS[M+Na-2H]-184.332859911
AllCCS[M+HCOO]-184.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SteviolCC12CCCC(C)(C1CCC13CC(=C)C(O)(C1)CCC23)C(O)=O3311.8Standard polar33892256
SteviolCC12CCCC(C)(C1CCC13CC(=C)C(O)(C1)CCC23)C(O)=O2435.1Standard non polar33892256
SteviolCC12CCCC(C)(C1CCC13CC(=C)C(O)(C1)CCC23)C(O)=O2571.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Steviol,1TMS,isomer #1C=C1CC23CCC4C(C)(C(=O)O)CCCC4(C)C2CCC1(O[Si](C)(C)C)C32646.3Semi standard non polar33892256
Steviol,1TMS,isomer #2C=C1CC23CCC4C(C)(C(=O)O[Si](C)(C)C)CCCC4(C)C2CCC1(O)C32494.4Semi standard non polar33892256
Steviol,2TMS,isomer #1C=C1CC23CCC4C(C)(C(=O)O[Si](C)(C)C)CCCC4(C)C2CCC1(O[Si](C)(C)C)C32521.4Semi standard non polar33892256
Steviol,1TBDMS,isomer #1C=C1CC23CCC4C(C)(C(=O)O)CCCC4(C)C2CCC1(O[Si](C)(C)C(C)(C)C)C32910.5Semi standard non polar33892256
Steviol,1TBDMS,isomer #2C=C1CC23CCC4C(C)(C(=O)O[Si](C)(C)C(C)(C)C)CCCC4(C)C2CCC1(O)C32783.0Semi standard non polar33892256
Steviol,2TBDMS,isomer #1C=C1CC23CCC4C(C)(C(=O)O[Si](C)(C)C(C)(C)C)CCCC4(C)C2CCC1(O[Si](C)(C)C(C)(C)C)C33039.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Steviol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udl-0192000000-de1090a4ec1533cb323c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Steviol GC-MS (2 TMS) - 70eV, Positivesplash10-0092-7036900000-a2aed9f4962f4d61b3bf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Steviol 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 - Steviol 10V, Positive-QTOFsplash10-0uxr-0049000000-5ae9a49dfa780b709aaa2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Steviol 20V, Positive-QTOFsplash10-0zgi-0295000000-de545938e500f87f71372015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Steviol 40V, Positive-QTOFsplash10-0pvl-3960000000-187f3853f760d905241c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Steviol 10V, Negative-QTOFsplash10-014i-0069000000-efddc327a3da1c119a4d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Steviol 20V, Negative-QTOFsplash10-0601-0093000000-f5154216ed6952d774ec2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Steviol 40V, Negative-QTOFsplash10-0ab9-1091000000-7c1aee023932b02e7beb2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Steviol 10V, Negative-QTOFsplash10-014i-0009000000-062ad2a35e11d303cf232021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Steviol 20V, Negative-QTOFsplash10-014i-0009000000-062ad2a35e11d303cf232021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Steviol 40V, Negative-QTOFsplash10-014i-2029000000-20b48f0aaf7fb62a56c32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Steviol 10V, Positive-QTOFsplash10-00xr-0095000000-18d0bd8a33d68ee36ccb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Steviol 20V, Positive-QTOFsplash10-05xr-0092000000-6cbbad8923153dd4cebd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Steviol 40V, Positive-QTOFsplash10-067i-4961000000-5bea034cb1da2fd59ca82021-09-25Wishart 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 IDFDB015642
KNApSAcK IDC00034695
Chemspider ID277096
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSteviol
METLIN IDNot Available
PubChem Compound313280
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1014791
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.