Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:25:33 UTC
Update Date2022-03-07 02:56:23 UTC
HMDB IDHMDB0039886
Secondary Accession Numbers
  • HMDB39886
Metabolite Identification
Common Name16-Methyl-epi-nigakihemiacetal B
Description16-Methyl-epi-nigakihemiacetal B belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. 16-Methyl-epi-nigakihemiacetal B is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863454
SynonymsNot Available
Chemical FormulaC23H32O6
Average Molecular Weight404.4966
Monoisotopic Molecular Weight404.219888756
IUPAC Name4,11,15-trimethoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-4,14-diene-3,16-dione
Traditional Name4,11,15-trimethoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-4,14-diene-3,16-dione
CAS Registry NumberNot Available
SMILES
COC1CC2C(C)=C(OC)C(=O)C3C2(C)C(CC2C(C)C=C(OC)C(=O)C32C)O1
InChI Identifier
InChI=1S/C23H32O6/c1-11-8-15(26-5)21(25)23(4)13(11)9-16-22(3)14(10-17(27-6)29-16)12(2)19(28-7)18(24)20(22)23/h8,11,13-14,16-17,20H,9-10H2,1-7H3
InChI KeyMSXBIQMJEOYRDV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentQuassinoids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point173 - 176 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP3.05ALOGPS
logP2.67ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)18.31ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area71.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity110.34 m³·mol⁻¹ChemAxon
Polarizability44.01 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]+196.44931661259
DarkChem[M-H]-190.73931661259
DeepCCS[M-2H]-224.83430932474
DeepCCS[M+Na]+200.06230932474
AllCCS[M+H]+195.532859911
AllCCS[M+H-H2O]+193.132859911
AllCCS[M+NH4]+197.732859911
AllCCS[M+Na]+198.332859911
AllCCS[M-H]-201.632859911
AllCCS[M+Na-2H]-202.432859911
AllCCS[M+HCOO]-203.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
16-Methyl-epi-nigakihemiacetal BCOC1CC2C(C)=C(OC)C(=O)C3C2(C)C(CC2C(C)C=C(OC)C(=O)C32C)O13871.3Standard polar33892256
16-Methyl-epi-nigakihemiacetal BCOC1CC2C(C)=C(OC)C(=O)C3C2(C)C(CC2C(C)C=C(OC)C(=O)C32C)O12679.1Standard non polar33892256
16-Methyl-epi-nigakihemiacetal BCOC1CC2C(C)=C(OC)C(=O)C3C2(C)C(CC2C(C)C=C(OC)C(=O)C32C)O12916.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
16-Methyl-epi-nigakihemiacetal B,1TMS,isomer #1COC1=CC(C)C2CC3OC(OC)CC4C(C)=C(OC)C(O[Si](C)(C)C)=C(C2(C)C1=O)C34C2885.8Semi standard non polar33892256
16-Methyl-epi-nigakihemiacetal B,1TMS,isomer #1COC1=CC(C)C2CC3OC(OC)CC4C(C)=C(OC)C(O[Si](C)(C)C)=C(C2(C)C1=O)C34C2818.8Standard non polar33892256
16-Methyl-epi-nigakihemiacetal B,1TBDMS,isomer #1COC1=CC(C)C2CC3OC(OC)CC4C(C)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C(C2(C)C1=O)C34C3105.2Semi standard non polar33892256
16-Methyl-epi-nigakihemiacetal B,1TBDMS,isomer #1COC1=CC(C)C2CC3OC(OC)CC4C(C)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C(C2(C)C1=O)C34C3034.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 16-Methyl-epi-nigakihemiacetal B GC-MS (Non-derivatized) - 70eV, Positivesplash10-00g0-0219000000-c817d1306384f25518942017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Methyl-epi-nigakihemiacetal 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 - 16-Methyl-epi-nigakihemiacetal B 10V, Positive-QTOFsplash10-0a4i-0009700000-8105d6f32f5c61212a652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Methyl-epi-nigakihemiacetal B 20V, Positive-QTOFsplash10-056v-0019100000-96237818523f962e08502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Methyl-epi-nigakihemiacetal B 40V, Positive-QTOFsplash10-0gb9-4195000000-75caeec13d68b51a91d12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Methyl-epi-nigakihemiacetal B 10V, Negative-QTOFsplash10-0udi-0002900000-76f8e95edf2a60dab5932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Methyl-epi-nigakihemiacetal B 20V, Negative-QTOFsplash10-0uk9-0009400000-0db3f277ff508b0fadbd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Methyl-epi-nigakihemiacetal B 40V, Negative-QTOFsplash10-0a4i-9028000000-b1817348e9bbc5918f222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Methyl-epi-nigakihemiacetal B 10V, Negative-QTOFsplash10-0udi-0000900000-421147e2847d7801cbe42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Methyl-epi-nigakihemiacetal B 20V, Negative-QTOFsplash10-0udi-0009700000-49d35d8243989678e1892021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Methyl-epi-nigakihemiacetal B 40V, Negative-QTOFsplash10-0zfr-0009300000-5c50c986edf8165a6cf22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Methyl-epi-nigakihemiacetal B 10V, Positive-QTOFsplash10-0a4i-0001900000-b37c3423e0bf33919def2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Methyl-epi-nigakihemiacetal B 20V, Positive-QTOFsplash10-0a4i-0029400000-7ecd729cda97b871f5612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Methyl-epi-nigakihemiacetal B 40V, Positive-QTOFsplash10-0uyi-4039000000-78a5b36c73e90f2694112021-09-22Wishart 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 IDFDB019545
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound85234534
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.