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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:25 UTC
Update Date2022-03-07 02:52:24 UTC
HMDB IDHMDB0030047
Secondary Accession Numbers
  • HMDB30047
Metabolite Identification
Common NameNeotigogenin
DescriptionNeogrifolin belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Neogrifolin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563861929
Synonyms
ValueSource
5-Methyl-6-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-1,3-benzenediolHMDB
e,e,5-Methyl-4-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-1,3-benzenediolHMDB
4-Farnesyl-5-methylresorcinolMeSH
4-trans,trans-Farnesyl-5-methylresorcinolMeSH
(25S)-5alpha-Spirostan-3beta-olHMDB
(3beta,5alpha,25S)-Spirostan-3-olHMDB
25S-TigogeninHMDB
Chemical FormulaC27H44O3
Average Molecular Weight416.6365
Monoisotopic Molecular Weight416.329045274
IUPAC Name(1'R,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'S,16'S,18'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-ol
Traditional Name(1'R,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'S,16'S,18'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-ol
CAS Registry Number470-01-9
SMILES
[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@H](C)CO1)O2
InChI Identifier
InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1
InChI KeyGMBQZIIUCVWOCD-PUHUBZITSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • Resorcinol
  • M-cresol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point202 - 203 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.3e-05 g/LALOGPS
logP4.52ALOGPS
logP5.33ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity119.42 m³·mol⁻¹ChemAxon
Polarizability50.87 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-222.03530932474
DeepCCS[M+Na]+196.40630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Neotigogenin[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@H](C)CO1)O22681.0Standard polar33892256
Neotigogenin[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@H](C)CO1)O23236.6Standard non polar33892256
Neotigogenin[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@H](C)CO1)O23397.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Neotigogenin,1TMS,isomer #1C[C@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[Si](C)(C)C)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C3297.8Semi standard non polar33892256
Neotigogenin,1TBDMS,isomer #1C[C@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C3586.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Neotigogenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pbi-2129100000-ce00917c9402bf19f2cb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neotigogenin GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-4217900000-31efb237b024e3b8920a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neotigogenin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neotigogenin 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 - Neotigogenin 10V, Positive-QTOFsplash10-014j-5039500000-2dc535b52346682944292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neotigogenin 20V, Positive-QTOFsplash10-0avi-5094100000-73cb8de52ed2c81a60082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neotigogenin 40V, Positive-QTOFsplash10-0pvi-9055000000-cd920b055b8c4a5478c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neotigogenin 10V, Negative-QTOFsplash10-014i-5003900000-c46f2a81526a3824ec012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neotigogenin 20V, Negative-QTOFsplash10-014j-2019200000-3a3da9fcf5a22a3b29932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neotigogenin 40V, Negative-QTOFsplash10-0gb9-9025000000-662616db765aefc27d752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neotigogenin 10V, Positive-QTOFsplash10-014i-0043900000-2b302fdea4f63c5306c12021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neotigogenin 20V, Positive-QTOFsplash10-0ar0-1193300000-17ee1df0d3203669d2c32021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neotigogenin 40V, Positive-QTOFsplash10-00b9-2590000000-9a82cac1ff37947e3a4a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neotigogenin 10V, Negative-QTOFsplash10-014i-0000900000-67ea14fb7a26b9b2d9292021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neotigogenin 20V, Negative-QTOFsplash10-014i-0001900000-ff4f5d155a47a38a5c072021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neotigogenin 40V, Negative-QTOFsplash10-02ta-0229700000-519f15705a81d147ae882021-09-25Wishart 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 IDFDB001359
KNApSAcK IDC00023938
Chemspider ID8050115
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9874426
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.