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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:02:45 UTC
Update Date2022-03-07 02:56:59 UTC
HMDB IDHMDB0041367
Secondary Accession Numbers
  • HMDB41367
Metabolite Identification
Common Name25-Cinnamoyl-vulgaroside
Description25-Cinnamoyl-vulgaroside belongs to the class of organic compounds known as cheilanthane sesterterpenoids. These are sesterterpnoids with a structure based on the cheilanthane backbone. Cheilanthane is a tricyclic compound consisting of a tetradecahydrophenanthrene ring system that carries two methyl groups at the 1-position, one methyl group at the 4a-,7-, and 8a-positions, as well as a 3-methylpentyl group at the 8-position. Based on a literature review a small amount of articles have been published on 25-Cinnamoyl-vulgaroside.
Structure
Thumb
Synonyms
ValueSource
3-{1-hydroxy-2-[2-hydroxy-2-(hydroxymethyl)-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-1-yl]ethyl}-5-oxo-2,5-dihydrofuran-2-yl (2E)-3-phenylprop-2-enoic acidHMDB
Chemical FormulaC34H46O7
Average Molecular Weight566.7248
Monoisotopic Molecular Weight566.324353826
IUPAC Name3-{1-hydroxy-2-[2-hydroxy-2-(hydroxymethyl)-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-1-yl]ethyl}-5-oxo-2,5-dihydrofuran-2-yl (2E)-3-phenylprop-2-enoate
Traditional Name3-{1-hydroxy-2-[2-hydroxy-2-(hydroxymethyl)-4b,8,8,10a-tetramethyl-decahydrophenanthren-1-yl]ethyl}-5-oxo-2H-furan-2-yl (2E)-3-phenylprop-2-enoate
CAS Registry Number172616-90-9
SMILES
CC1(C)CCCC2(C)C1CCC1(C)C(CC(O)C3=CC(=O)OC3OC(=O)\C=C\C3=CC=CC=C3)C(O)(CO)CCC21
InChI Identifier
InChI=1S/C34H46O7/c1-31(2)15-8-16-32(3)25(31)13-17-33(4)26(32)14-18-34(39,21-35)27(33)20-24(36)23-19-29(38)41-30(23)40-28(37)12-11-22-9-6-5-7-10-22/h5-7,9-12,19,24-27,30,35-36,39H,8,13-18,20-21H2,1-4H3/b12-11+
InChI KeySXPHINZZVYORPV-VAWYXSNFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cheilanthane sesterterpenoids. These are sesterterpnoids with a structure based on the cheilanthane backbone. Cheilanthane is a tricyclic compound consisting of a tetradecahydrophenanthrene ring system that carries two methyl groups at the 1-position, one methyl group at the 4a-,7-, and 8a-positions, as well as a 3-methylpentyl group at the 8-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentCheilanthane sesterterpenoids
Alternative Parents
Substituents
  • Cheilanthane sesterterpenoid
  • 18-hydroxysteroid
  • 13-hydroxysteroid
  • Hydroxysteroid
  • 16-hydroxysteroid
  • 17-hydroxysteroid
  • Steroid
  • Hydrophenanthrene
  • Phenanthrene
  • Cinnamic acid or derivatives
  • Cinnamic acid ester
  • Styrene
  • Acylal
  • Fatty acid ester
  • Benzenoid
  • Fatty acyl
  • Monocyclic benzene moiety
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Cyclic alcohol
  • Dihydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Acetal
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 Solubility0.0014 g/LALOGPS
logP4.34ALOGPS
logP5.82ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity156.74 m³·mol⁻¹ChemAxon
Polarizability62.92 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+230.94131661259
DarkChem[M-H]-221.94131661259
DeepCCS[M-2H]-258.18930932474
DeepCCS[M+Na]+233.61230932474
AllCCS[M+H]+235.032859911
AllCCS[M+H-H2O]+233.832859911
AllCCS[M+NH4]+236.132859911
AllCCS[M+Na]+236.432859911
AllCCS[M-H]-224.232859911
AllCCS[M+Na-2H]-227.132859911
AllCCS[M+HCOO]-230.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
25-Cinnamoyl-vulgarosideCC1(C)CCCC2(C)C1CCC1(C)C(CC(O)C3=CC(=O)OC3OC(=O)\C=C\C3=CC=CC=C3)C(O)(CO)CCC214302.1Standard polar33892256
25-Cinnamoyl-vulgarosideCC1(C)CCCC2(C)C1CCC1(C)C(CC(O)C3=CC(=O)OC3OC(=O)\C=C\C3=CC=CC=C3)C(O)(CO)CCC214373.4Standard non polar33892256
25-Cinnamoyl-vulgarosideCC1(C)CCCC2(C)C1CCC1(C)C(CC(O)C3=CC(=O)OC3OC(=O)\C=C\C3=CC=CC=C3)C(O)(CO)CCC214982.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
25-Cinnamoyl-vulgaroside,1TMS,isomer #1CC1(C)CCCC2(C)C1CCC1(C)C(CC(O[Si](C)(C)C)C3=CC(=O)OC3OC(=O)/C=C/C3=CC=CC=C3)C(O)(CO)CCC214682.2Semi standard non polar33892256
25-Cinnamoyl-vulgaroside,1TMS,isomer #2CC1(C)CCCC2(C)C1CCC1(C)C(CC(O)C3=CC(=O)OC3OC(=O)/C=C/C3=CC=CC=C3)C(CO)(O[Si](C)(C)C)CCC214636.2Semi standard non polar33892256
25-Cinnamoyl-vulgaroside,1TMS,isomer #3CC1(C)CCCC2(C)C1CCC1(C)C(CC(O)C3=CC(=O)OC3OC(=O)/C=C/C3=CC=CC=C3)C(O)(CO[Si](C)(C)C)CCC214638.9Semi standard non polar33892256
25-Cinnamoyl-vulgaroside,2TMS,isomer #1CC1(C)CCCC2(C)C1CCC1(C)C(CC(O[Si](C)(C)C)C3=CC(=O)OC3OC(=O)/C=C/C3=CC=CC=C3)C(CO)(O[Si](C)(C)C)CCC214566.1Semi standard non polar33892256
25-Cinnamoyl-vulgaroside,2TMS,isomer #2CC1(C)CCCC2(C)C1CCC1(C)C(CC(O[Si](C)(C)C)C3=CC(=O)OC3OC(=O)/C=C/C3=CC=CC=C3)C(O)(CO[Si](C)(C)C)CCC214561.3Semi standard non polar33892256
25-Cinnamoyl-vulgaroside,2TMS,isomer #3CC1(C)CCCC2(C)C1CCC1(C)C(CC(O)C3=CC(=O)OC3OC(=O)/C=C/C3=CC=CC=C3)C(CO[Si](C)(C)C)(O[Si](C)(C)C)CCC214551.4Semi standard non polar33892256
25-Cinnamoyl-vulgaroside,3TMS,isomer #1CC1(C)CCCC2(C)C1CCC1(C)C(CC(O[Si](C)(C)C)C3=CC(=O)OC3OC(=O)/C=C/C3=CC=CC=C3)C(CO[Si](C)(C)C)(O[Si](C)(C)C)CCC214484.4Semi standard non polar33892256
25-Cinnamoyl-vulgaroside,1TBDMS,isomer #1CC1(C)CCCC2(C)C1CCC1(C)C(CC(O[Si](C)(C)C(C)(C)C)C3=CC(=O)OC3OC(=O)/C=C/C3=CC=CC=C3)C(O)(CO)CCC214905.6Semi standard non polar33892256
25-Cinnamoyl-vulgaroside,1TBDMS,isomer #2CC1(C)CCCC2(C)C1CCC1(C)C(CC(O)C3=CC(=O)OC3OC(=O)/C=C/C3=CC=CC=C3)C(CO)(O[Si](C)(C)C(C)(C)C)CCC214854.1Semi standard non polar33892256
25-Cinnamoyl-vulgaroside,1TBDMS,isomer #3CC1(C)CCCC2(C)C1CCC1(C)C(CC(O)C3=CC(=O)OC3OC(=O)/C=C/C3=CC=CC=C3)C(O)(CO[Si](C)(C)C(C)(C)C)CCC214856.7Semi standard non polar33892256
25-Cinnamoyl-vulgaroside,2TBDMS,isomer #1CC1(C)CCCC2(C)C1CCC1(C)C(CC(O[Si](C)(C)C(C)(C)C)C3=CC(=O)OC3OC(=O)/C=C/C3=CC=CC=C3)C(CO)(O[Si](C)(C)C(C)(C)C)CCC214995.6Semi standard non polar33892256
25-Cinnamoyl-vulgaroside,2TBDMS,isomer #2CC1(C)CCCC2(C)C1CCC1(C)C(CC(O[Si](C)(C)C(C)(C)C)C3=CC(=O)OC3OC(=O)/C=C/C3=CC=CC=C3)C(O)(CO[Si](C)(C)C(C)(C)C)CCC214993.0Semi standard non polar33892256
25-Cinnamoyl-vulgaroside,2TBDMS,isomer #3CC1(C)CCCC2(C)C1CCC1(C)C(CC(O)C3=CC(=O)OC3OC(=O)/C=C/C3=CC=CC=C3)C(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)CCC214980.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 25-Cinnamoyl-vulgaroside GC-MS (Non-derivatized) - 70eV, Positivesplash10-001r-0622190000-1fea89fa870efd1d53292017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Cinnamoyl-vulgaroside GC-MS (1 TMS) - 70eV, Positivesplash10-05gi-2830219000-b3d289a752edad64cf682017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Cinnamoyl-vulgaroside GC-MS ("25-Cinnamoyl-vulgaroside,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Cinnamoyl-vulgaroside GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Cinnamoyl-vulgaroside GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Cinnamoyl-vulgaroside GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Cinnamoyl-vulgaroside GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Cinnamoyl-vulgaroside GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Cinnamoyl-vulgaroside GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Cinnamoyl-vulgaroside GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Cinnamoyl-vulgaroside GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Cinnamoyl-vulgaroside GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Cinnamoyl-vulgaroside GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Cinnamoyl-vulgaroside GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Cinnamoyl-vulgaroside GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Cinnamoyl-vulgaroside 10V, Positive-QTOFsplash10-00ls-1501390000-c0d996156f467393f52b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Cinnamoyl-vulgaroside 20V, Positive-QTOFsplash10-001i-0912430000-930c2fccfc8d50c0311c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Cinnamoyl-vulgaroside 40V, Positive-QTOFsplash10-0uys-4947610000-ab6528ee2c4ba85b6e462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Cinnamoyl-vulgaroside 10V, Negative-QTOFsplash10-004i-0900160000-33d47e05d3f2bdb6ee032017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Cinnamoyl-vulgaroside 20V, Negative-QTOFsplash10-004r-5749730000-1aa7a7e77db6a6344ff82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Cinnamoyl-vulgaroside 40V, Negative-QTOFsplash10-056u-5906200000-b54c4761cc871fc3d3592017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Cinnamoyl-vulgaroside 10V, Negative-QTOFsplash10-014i-0200590000-da930405bde3bc5f5ae02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Cinnamoyl-vulgaroside 20V, Negative-QTOFsplash10-014i-0501190000-9ebaead4d187b1d562b12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Cinnamoyl-vulgaroside 40V, Negative-QTOFsplash10-0fb9-9710110000-d8c9b4d73857b318bc5f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Cinnamoyl-vulgaroside 10V, Positive-QTOFsplash10-014i-0400490000-6a05c75d5e34c12cc5d62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Cinnamoyl-vulgaroside 20V, Positive-QTOFsplash10-0ue9-0900010000-00fd7c688402f2f414c52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Cinnamoyl-vulgaroside 40V, Positive-QTOFsplash10-0udi-3900110000-20b66abbafc183743c672021-09-25Wishart 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 IDFDB021292
KNApSAcK IDNot Available
Chemspider ID35015161
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131753123
PDB IDNot Available
ChEBI ID176068
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.