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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:09 UTC
Update Date2022-03-07 02:53:26 UTC
HMDB IDHMDB0032680
Secondary Accession Numbers
  • HMDB32680
Metabolite Identification
Common NameNeoporrigenin B
DescriptionNeoporrigenin B belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Neoporrigenin B is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862292
Synonyms
ValueSource
(-)-Neoporrigenin bHMDB
3,6-Dihydroxy-(3beta,5alpha,6beta,25S)-spirostan-2-oneHMDB
Chemical FormulaC27H42O5
Average Molecular Weight446.6194
Monoisotopic Molecular Weight446.303224454
IUPAC Name16',19'-dihydroxy-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-15'-one
Traditional Name16',19'-dihydroxy-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-15'-one
CAS Registry Number196607-74-6
SMILES
CC1C2C(CC3C4CC(O)C5CC(O)C(=O)CC5(C)C4CCC23C)OC11CCC(C)CO1
InChI Identifier
InChI=1S/C27H42O5/c1-14-5-8-27(31-13-14)15(2)24-23(32-27)11-18-16-9-20(28)19-10-21(29)22(30)12-26(19,4)17(16)6-7-25(18,24)3/h14-21,23-24,28-29H,5-13H2,1-4H3
InChI KeyBTSHHJQHTVNSLW-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
  • Oxosteroid
  • 2-oxosteroid
  • Steroid
  • Ketal
  • Oxane
  • Tetrahydrofuran
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0079 g/LALOGPS
logP2.11ALOGPS
logP3.36ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)13.38ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity121.47 m³·mol⁻¹ChemAxon
Polarizability51.35 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]+203.1531661259
DarkChem[M-H]-197.44531661259
DeepCCS[M-2H]-244.83130932474
DeepCCS[M+Na]+220.05930932474
AllCCS[M+H]+212.632859911
AllCCS[M+H-H2O]+210.632859911
AllCCS[M+NH4]+214.332859911
AllCCS[M+Na]+214.832859911
AllCCS[M-H]-209.932859911
AllCCS[M+Na-2H]-211.632859911
AllCCS[M+HCOO]-213.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Neoporrigenin BCC1C2C(CC3C4CC(O)C5CC(O)C(=O)CC5(C)C4CCC23C)OC11CCC(C)CO12947.5Standard polar33892256
Neoporrigenin BCC1C2C(CC3C4CC(O)C5CC(O)C(=O)CC5(C)C4CCC23C)OC11CCC(C)CO13283.6Standard non polar33892256
Neoporrigenin BCC1C2C(CC3C4CC(O)C5CC(O)C(=O)CC5(C)C4CCC23C)OC11CCC(C)CO13634.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Neoporrigenin B,1TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)C5CC(O)C(=O)CC5(C)C4CCC3(C)C1C2C3693.0Semi standard non polar33892256
Neoporrigenin B,1TMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O[Si](C)(C)C)C(=O)CC5(C)C4CCC3(C)C1C2C3689.4Semi standard non polar33892256
Neoporrigenin B,1TMS,isomer #3CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O)=C(O[Si](C)(C)C)CC5(C)C4CCC3(C)C1C2C3671.2Semi standard non polar33892256
Neoporrigenin B,1TMS,isomer #4CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O)C(O[Si](C)(C)C)=CC5(C)C4CCC3(C)C1C2C3653.4Semi standard non polar33892256
Neoporrigenin B,2TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)C5CC(O[Si](C)(C)C)C(=O)CC5(C)C4CCC3(C)C1C2C3627.5Semi standard non polar33892256
Neoporrigenin B,2TMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)C5CC(O)=C(O[Si](C)(C)C)CC5(C)C4CCC3(C)C1C2C3598.2Semi standard non polar33892256
Neoporrigenin B,2TMS,isomer #3CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)C5CC(O)C(O[Si](C)(C)C)=CC5(C)C4CCC3(C)C1C2C3561.3Semi standard non polar33892256
Neoporrigenin B,2TMS,isomer #4CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)CC5(C)C4CCC3(C)C1C2C3668.1Semi standard non polar33892256
Neoporrigenin B,2TMS,isomer #5CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC5(C)C4CCC3(C)C1C2C3583.9Semi standard non polar33892256
Neoporrigenin B,3TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)C5CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)CC5(C)C4CCC3(C)C1C2C3620.3Semi standard non polar33892256
Neoporrigenin B,3TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)C5CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)CC5(C)C4CCC3(C)C1C2C3438.0Standard non polar33892256
Neoporrigenin B,3TMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)C5CC(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC5(C)C4CCC3(C)C1C2C3518.3Semi standard non polar33892256
Neoporrigenin B,3TMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)C5CC(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC5(C)C4CCC3(C)C1C2C3371.4Standard non polar33892256
Neoporrigenin B,1TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O)C(=O)CC5(C)C4CCC3(C)C1C2C3906.7Semi standard non polar33892256
Neoporrigenin B,1TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O[Si](C)(C)C(C)(C)C)C(=O)CC5(C)C4CCC3(C)C1C2C3908.0Semi standard non polar33892256
Neoporrigenin B,1TBDMS,isomer #3CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O)=C(O[Si](C)(C)C(C)(C)C)CC5(C)C4CCC3(C)C1C2C3917.9Semi standard non polar33892256
Neoporrigenin B,1TBDMS,isomer #4CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O)C(O[Si](C)(C)C(C)(C)C)=CC5(C)C4CCC3(C)C1C2C3883.5Semi standard non polar33892256
Neoporrigenin B,2TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O[Si](C)(C)C(C)(C)C)C(=O)CC5(C)C4CCC3(C)C1C2C4071.9Semi standard non polar33892256
Neoporrigenin B,2TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O)=C(O[Si](C)(C)C(C)(C)C)CC5(C)C4CCC3(C)C1C2C4067.3Semi standard non polar33892256
Neoporrigenin B,2TBDMS,isomer #3CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O)C(O[Si](C)(C)C(C)(C)C)=CC5(C)C4CCC3(C)C1C2C4024.9Semi standard non polar33892256
Neoporrigenin B,2TBDMS,isomer #4CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC5(C)C4CCC3(C)C1C2C4117.4Semi standard non polar33892256
Neoporrigenin B,2TBDMS,isomer #5CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC5(C)C4CCC3(C)C1C2C4034.1Semi standard non polar33892256
Neoporrigenin B,3TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC5(C)C4CCC3(C)C1C2C4261.7Semi standard non polar33892256
Neoporrigenin B,3TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC5(C)C4CCC3(C)C1C2C3971.7Standard non polar33892256
Neoporrigenin B,3TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC5(C)C4CCC3(C)C1C2C4172.4Semi standard non polar33892256
Neoporrigenin B,3TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC5(C)C4CCC3(C)C1C2C3952.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Neoporrigenin B GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2135900000-9f5cac4bb1e075aaf43d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoporrigenin B GC-MS (2 TMS) - 70eV, Positivesplash10-004i-4120790000-5cb269e8ab3575fcb55f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoporrigenin B GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoporrigenin B 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 - Neoporrigenin B 10V, Positive-QTOFsplash10-004j-4003900000-21f0a777a451936017282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoporrigenin B 20V, Positive-QTOFsplash10-000i-7097600000-4f04f7af4f1619cf24ef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoporrigenin B 40V, Positive-QTOFsplash10-014i-9033000000-8eb4c54eb89c410029cf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoporrigenin B 10V, Negative-QTOFsplash10-0002-4001900000-01eb314ca1bc5f53ccc72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoporrigenin B 20V, Negative-QTOFsplash10-0032-2008900000-e8760f1f4da238cfc8162016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoporrigenin B 40V, Negative-QTOFsplash10-014i-9006000000-0b3aaa0b1794038e8da72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoporrigenin B 10V, Positive-QTOFsplash10-0002-0001900000-6d5857f03066792f93d02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoporrigenin B 20V, Positive-QTOFsplash10-002b-0024900000-3f14c589c58be08dbcc02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoporrigenin B 40V, Positive-QTOFsplash10-056r-1958000000-3330f306813c2456e62f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoporrigenin B 10V, Negative-QTOFsplash10-0002-0000900000-cab8b24b67725b2134432021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoporrigenin B 20V, Negative-QTOFsplash10-0002-0000900000-7fd33831b2f9c20ba0512021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoporrigenin B 40V, Negative-QTOFsplash10-009e-0004900000-dd5220395ae0d43b95682021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB010635
KNApSAcK IDNot Available
Chemspider ID26503842
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53463026
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.