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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:31 UTC
Update Date2022-03-07 02:52:39 UTC
HMDB IDHMDB0030702
Secondary Accession Numbers
  • HMDB30702
Metabolite Identification
Common NameNeochlorogenin
DescriptionNeochlorogenin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Neochlorogenin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862024
Synonyms
ValueSource
(25S)-5alpha-Spirostan-3beta,6alpha-diolHMDB
ChlorogeninHMDB
Chemical FormulaC27H44O4
Average Molecular Weight432.6359
Monoisotopic Molecular Weight432.323959896
IUPAC Name5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16',19'-diol
Traditional Name5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16',19'-diol
CAS Registry Number511-91-1
SMILES
CC1C2C(CC3C4CC(O)C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CO1
InChI Identifier
InChI=1S/C27H44O4/c1-15-5-10-27(30-14-15)16(2)24-23(31-27)13-20-18-12-22(29)21-11-17(28)6-8-25(21,3)19(18)7-9-26(20,24)4/h15-24,28-29H,5-14H2,1-4H3
InChI KeyPZNPHSFXILSZTM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Spirostane skeleton
  • 3-hydroxysteroid
  • 6-hydroxysteroid
  • Hydroxysteroid
  • Steroid
  • Ketal
  • Oxane
  • Cyclic alcohol
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point262 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0024 g/LALOGPS
logP3.09ALOGPS
logP4.02ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)14.75ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity121.01 m³·mol⁻¹ChemAxon
Polarizability51.58 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+199.95431661259
DarkChem[M-H]-194.27431661259
DeepCCS[M-2H]-239.03230932474
DeepCCS[M+Na]+214.38530932474
AllCCS[M+H]+211.632859911
AllCCS[M+H-H2O]+209.632859911
AllCCS[M+NH4]+213.432859911
AllCCS[M+Na]+213.932859911
AllCCS[M-H]-207.332859911
AllCCS[M+Na-2H]-209.032859911
AllCCS[M+HCOO]-211.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NeochlorogeninCC1C2C(CC3C4CC(O)C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CO12810.8Standard polar33892256
NeochlorogeninCC1C2C(CC3C4CC(O)C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CO13228.3Standard non polar33892256
NeochlorogeninCC1C2C(CC3C4CC(O)C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CO13554.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Neochlorogenin,1TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)C5CC(O)CCC5(C)C4CCC3(C)C1C2C3469.7Semi standard non polar33892256
Neochlorogenin,1TMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C3519.2Semi standard non polar33892256
Neochlorogenin,2TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)C5CC(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C3453.7Semi standard non polar33892256
Neochlorogenin,1TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O)CCC5(C)C4CCC3(C)C1C2C3702.0Semi standard non polar33892256
Neochlorogenin,1TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C3752.9Semi standard non polar33892256
Neochlorogenin,2TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C3928.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Neochlorogenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-2349700000-faadb22e01b5b5b29e5a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neochlorogenin GC-MS (2 TMS) - 70eV, Positivesplash10-03di-4211690000-e07544629ae1491e35e22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neochlorogenin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neochlorogenin 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 - Neochlorogenin 10V, Positive-QTOFsplash10-014i-3025900000-ab789d16673aa4f9ee9c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neochlorogenin 20V, Positive-QTOFsplash10-00xr-4093300000-eae6c00ee5628b0bf6632015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neochlorogenin 40V, Positive-QTOFsplash10-066r-9056000000-bdc39a646b70aefcb2e92015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neochlorogenin 10V, Negative-QTOFsplash10-00lr-3001900000-c36743b21dd26006f1cc2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neochlorogenin 20V, Negative-QTOFsplash10-02u0-2009600000-c873ef3f6fd04e0485d52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neochlorogenin 40V, Negative-QTOFsplash10-014i-9006000000-51f04387d1f8e706bd902015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neochlorogenin 10V, Positive-QTOFsplash10-001i-0000900000-ebeb2136bc0d03c132292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neochlorogenin 20V, Positive-QTOFsplash10-00m0-0295700000-aa5ec1535a8186e030cd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neochlorogenin 40V, Positive-QTOFsplash10-00kb-3930000000-888c16d9f8bab1f7e6892021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neochlorogenin 10V, Negative-QTOFsplash10-001i-0000900000-f99193fc2ae16b7de32c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neochlorogenin 20V, Negative-QTOFsplash10-001i-0000900000-f99193fc2ae16b7de32c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neochlorogenin 40V, Negative-QTOFsplash10-00lr-0102900000-9661b709fc5af94ced872021-09-24Wishart 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 IDFDB002623
KNApSAcK IDNot Available
Chemspider ID510158
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound586922
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.