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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:02:41 UTC
Update Date2022-03-07 02:55:05 UTC
HMDB IDHMDB0036864
Secondary Accession Numbers
  • HMDB36864
Metabolite Identification
Common NameAnhydrocinnzeylanine
DescriptionAnhydrocinnzeylanine belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Anhydrocinnzeylanine is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862940
Synonyms
ValueSource
2,6,8-Trihydroxy-3,7,11-trimethyl-14-oxo-4-(propan-2-yl)-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetic acidGenerator
Chemical FormulaC22H32O7
Average Molecular Weight408.4853
Monoisotopic Molecular Weight408.214803378
IUPAC Name2,6,8-trihydroxy-3,7,11-trimethyl-14-oxo-4-(propan-2-yl)-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate
Traditional Name2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate
CAS Registry Number68799-62-2
SMILES
CC(C)C1=C(C)C2(O)C(O)(C1)C1(C)CC(=O)OC22C(OC(C)=O)C(C)CCC12O
InChI Identifier
InChI=1S/C22H32O7/c1-11(2)15-9-20(26)18(6)10-16(24)29-22(21(20,27)13(15)4)17(28-14(5)23)12(3)7-8-19(18,22)25/h11-12,17,25-27H,7-10H2,1-6H3
InChI KeyUEXGXCDLLOHGAS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point195 - 199 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.63 g/LALOGPS
logP1.21ALOGPS
logP0.88ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)11.9ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity102.35 m³·mol⁻¹ChemAxon
Polarizability42.66 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]+193.41531661259
DarkChem[M-H]-189.15131661259
DeepCCS[M-2H]-228.75530932474
DeepCCS[M+Na]+203.930932474
AllCCS[M+H]+193.032859911
AllCCS[M+H-H2O]+190.732859911
AllCCS[M+NH4]+195.132859911
AllCCS[M+Na]+195.732859911
AllCCS[M-H]-200.932859911
AllCCS[M+Na-2H]-201.632859911
AllCCS[M+HCOO]-202.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AnhydrocinnzeylanineCC(C)C1=C(C)C2(O)C(O)(C1)C1(C)CC(=O)OC22C(OC(C)=O)C(C)CCC12O4288.6Standard polar33892256
AnhydrocinnzeylanineCC(C)C1=C(C)C2(O)C(O)(C1)C1(C)CC(=O)OC22C(OC(C)=O)C(C)CCC12O2678.4Standard non polar33892256
AnhydrocinnzeylanineCC(C)C1=C(C)C2(O)C(O)(C1)C1(C)CC(=O)OC22C(OC(C)=O)C(C)CCC12O2822.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Anhydrocinnzeylanine,1TMS,isomer #1CC(=O)OC1C(C)CCC2(O)C3(C)CC(=O)OC12C1(O[Si](C)(C)C)C(C)=C(C(C)C)CC31O2905.9Semi standard non polar33892256
Anhydrocinnzeylanine,1TMS,isomer #2CC(=O)OC1C(C)CCC2(O)C3(C)CC(=O)OC12C1(O)C(C)=C(C(C)C)CC31O[Si](C)(C)C2910.4Semi standard non polar33892256
Anhydrocinnzeylanine,1TMS,isomer #3CC(=O)OC1C(C)CCC2(O[Si](C)(C)C)C3(C)CC(=O)OC12C1(O)C(C)=C(C(C)C)CC31O2900.5Semi standard non polar33892256
Anhydrocinnzeylanine,2TMS,isomer #1CC(=O)OC1C(C)CCC2(O[Si](C)(C)C)C3(C)CC(=O)OC12C1(O[Si](C)(C)C)C(C)=C(C(C)C)CC31O2917.3Semi standard non polar33892256
Anhydrocinnzeylanine,2TMS,isomer #2CC(=O)OC1C(C)CCC2(O)C3(C)CC(=O)OC12C1(O[Si](C)(C)C)C(C)=C(C(C)C)CC31O[Si](C)(C)C2922.6Semi standard non polar33892256
Anhydrocinnzeylanine,2TMS,isomer #3CC(=O)OC1C(C)CCC2(O[Si](C)(C)C)C3(C)CC(=O)OC12C1(O)C(C)=C(C(C)C)CC31O[Si](C)(C)C2912.9Semi standard non polar33892256
Anhydrocinnzeylanine,3TMS,isomer #1CC(=O)OC1C(C)CCC2(O[Si](C)(C)C)C3(C)CC(=O)OC12C1(O[Si](C)(C)C)C(C)=C(C(C)C)CC31O[Si](C)(C)C2936.2Semi standard non polar33892256
Anhydrocinnzeylanine,1TBDMS,isomer #1CC(=O)OC1C(C)CCC2(O)C3(C)CC(=O)OC12C1(O[Si](C)(C)C(C)(C)C)C(C)=C(C(C)C)CC31O3170.7Semi standard non polar33892256
Anhydrocinnzeylanine,1TBDMS,isomer #2CC(=O)OC1C(C)CCC2(O)C3(C)CC(=O)OC12C1(O)C(C)=C(C(C)C)CC31O[Si](C)(C)C(C)(C)C3170.2Semi standard non polar33892256
Anhydrocinnzeylanine,1TBDMS,isomer #3CC(=O)OC1C(C)CCC2(O[Si](C)(C)C(C)(C)C)C3(C)CC(=O)OC12C1(O)C(C)=C(C(C)C)CC31O3164.2Semi standard non polar33892256
Anhydrocinnzeylanine,2TBDMS,isomer #1CC(=O)OC1C(C)CCC2(O[Si](C)(C)C(C)(C)C)C3(C)CC(=O)OC12C1(O[Si](C)(C)C(C)(C)C)C(C)=C(C(C)C)CC31O3406.1Semi standard non polar33892256
Anhydrocinnzeylanine,2TBDMS,isomer #2CC(=O)OC1C(C)CCC2(O)C3(C)CC(=O)OC12C1(O[Si](C)(C)C(C)(C)C)C(C)=C(C(C)C)CC31O[Si](C)(C)C(C)(C)C3407.4Semi standard non polar33892256
Anhydrocinnzeylanine,2TBDMS,isomer #3CC(=O)OC1C(C)CCC2(O[Si](C)(C)C(C)(C)C)C3(C)CC(=O)OC12C1(O)C(C)=C(C(C)C)CC31O[Si](C)(C)C(C)(C)C3407.9Semi standard non polar33892256
Anhydrocinnzeylanine,3TBDMS,isomer #1CC(=O)OC1C(C)CCC2(O[Si](C)(C)C(C)(C)C)C3(C)CC(=O)OC12C1(O[Si](C)(C)C(C)(C)C)C(C)=C(C(C)C)CC31O[Si](C)(C)C(C)(C)C3635.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Anhydrocinnzeylanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2903000000-ea36a3502734354b918e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anhydrocinnzeylanine GC-MS (3 TMS) - 70eV, Positivesplash10-0a6r-9020033000-1d1a918e0ea4226b83252017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anhydrocinnzeylanine 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 - Anhydrocinnzeylanine 10V, Positive-QTOFsplash10-0a4j-0009400000-16bb49b43c93055b4edd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anhydrocinnzeylanine 20V, Positive-QTOFsplash10-014j-9007000000-76f7a61512976584c2402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anhydrocinnzeylanine 40V, Positive-QTOFsplash10-0gbc-9001000000-f08192e4f8edee2605ef2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anhydrocinnzeylanine 10V, Negative-QTOFsplash10-0a4i-3006900000-8001262475e28ed90efe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anhydrocinnzeylanine 20V, Negative-QTOFsplash10-0aos-3009100000-46159c7754d6a7ed3c0b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anhydrocinnzeylanine 40V, Negative-QTOFsplash10-0a4l-9005000000-3194eb962ad5db15958c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anhydrocinnzeylanine 10V, Negative-QTOFsplash10-0a4i-0000900000-721cae8747eb24f40fa32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anhydrocinnzeylanine 20V, Negative-QTOFsplash10-0a4i-7001900000-8e02cae75cc737ceb5552021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anhydrocinnzeylanine 40V, Negative-QTOFsplash10-0a4l-9201100000-684d36ffeb7c85eb4b452021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anhydrocinnzeylanine 10V, Positive-QTOFsplash10-0a4i-0001900000-df21b1b11a20f16d5e192021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anhydrocinnzeylanine 20V, Positive-QTOFsplash10-0a4i-1029700000-c99a55e0038f61b9d0802021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anhydrocinnzeylanine 40V, Positive-QTOFsplash10-0006-9211000000-ea9ebcb38dc13f6565652021-09-22Wishart 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 IDFDB015818
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752069
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.