Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:00:53 UTC
Update Date2022-03-07 02:55:05 UTC
HMDB IDHMDB0036836
Secondary Accession Numbers
  • HMDB36836
Metabolite Identification
Common NameCascarillin
DescriptionCascarillin belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. Based on a literature review a significant number of articles have been published on Cascarillin.
Structure
Data?1563862935
Synonyms
ValueSource
4-Formyl-4-[2-(furan-3-yl)-2-hydroxyethyl]-7,8-dihydroxy-3,8,8a-trimethyl-decahydronaphthalen-2-yl acetic acidHMDB
Chemical FormulaC22H32O7
Average Molecular Weight408.4853
Monoisotopic Molecular Weight408.214803378
IUPAC Name4-formyl-4-[2-(furan-3-yl)-2-hydroxyethyl]-7,8-dihydroxy-3,8,8a-trimethyl-decahydronaphthalen-2-yl acetate
Traditional Name4-formyl-4-[2-(furan-3-yl)-2-hydroxyethyl]-7,8-dihydroxy-3,8,8a-trimethyl-hexahydro-1H-naphthalen-2-yl acetate
CAS Registry Number10118-56-6
SMILES
CC1C(CC2(C)C(CCC(O)C2(C)O)C1(CC(O)C1=COC=C1)C=O)OC(C)=O
InChI Identifier
InChI=1S/C22H32O7/c1-13-17(29-14(2)24)10-20(3)18(5-6-19(26)21(20,4)27)22(13,12-23)9-16(25)15-7-8-28-11-15/h7-8,11-13,16-19,25-27H,5-6,9-10H2,1-4H3
InChI KeyZOWKQQIGQBVKSV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentColensane and clerodane diterpenoids
Alternative Parents
Substituents
  • Clerodane diterpenoid
  • Cyclic alcohol
  • Furan
  • Tertiary alcohol
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Aldehyde
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point203.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility96.99 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP1.31ALOGPS
logP0.91ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)13.37ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.2 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity104.53 m³·mol⁻¹ChemAxon
Polarizability42.87 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.6631661259
DarkChem[M-H]-185.16331661259
DeepCCS[M+H]+196.39330932474
DeepCCS[M-H]-194.03530932474
DeepCCS[M-2H]-228.22930932474
DeepCCS[M+Na]+204.10730932474
AllCCS[M+H]+197.632859911
AllCCS[M+H-H2O]+195.232859911
AllCCS[M+NH4]+199.932859911
AllCCS[M+Na]+200.532859911
AllCCS[M-H]-199.832859911
AllCCS[M+Na-2H]-200.732859911
AllCCS[M+HCOO]-201.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CascarillinCC1C(CC2(C)C(CCC(O)C2(C)O)C1(CC(O)C1=COC=C1)C=O)OC(C)=O3807.8Standard polar33892256
CascarillinCC1C(CC2(C)C(CCC(O)C2(C)O)C1(CC(O)C1=COC=C1)C=O)OC(C)=O2660.5Standard non polar33892256
CascarillinCC1C(CC2(C)C(CCC(O)C2(C)O)C1(CC(O)C1=COC=C1)C=O)OC(C)=O3083.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cascarillin,1TMS,isomer #1CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C)C2(C)O)C(C=O)(CC(O)C2=COC=C2)C1C3025.8Semi standard non polar33892256
Cascarillin,1TMS,isomer #2CC(=O)OC1CC2(C)C(CCC(O)C2(C)O[Si](C)(C)C)C(C=O)(CC(O)C2=COC=C2)C1C3024.7Semi standard non polar33892256
Cascarillin,1TMS,isomer #3CC(=O)OC1CC2(C)C(CCC(O)C2(C)O)C(C=O)(CC(O[Si](C)(C)C)C2=COC=C2)C1C3080.9Semi standard non polar33892256
Cascarillin,2TMS,isomer #1CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C)C2(C)O[Si](C)(C)C)C(C=O)(CC(O)C2=COC=C2)C1C2998.8Semi standard non polar33892256
Cascarillin,2TMS,isomer #2CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C)C2(C)O)C(C=O)(CC(O[Si](C)(C)C)C2=COC=C2)C1C2971.4Semi standard non polar33892256
Cascarillin,2TMS,isomer #3CC(=O)OC1CC2(C)C(CCC(O)C2(C)O[Si](C)(C)C)C(C=O)(CC(O[Si](C)(C)C)C2=COC=C2)C1C2985.3Semi standard non polar33892256
Cascarillin,3TMS,isomer #1CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C)C2(C)O[Si](C)(C)C)C(C=O)(CC(O[Si](C)(C)C)C2=COC=C2)C1C2961.0Semi standard non polar33892256
Cascarillin,1TBDMS,isomer #1CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C(C)(C)C)C2(C)O)C(C=O)(CC(O)C2=COC=C2)C1C3270.2Semi standard non polar33892256
Cascarillin,1TBDMS,isomer #2CC(=O)OC1CC2(C)C(CCC(O)C2(C)O[Si](C)(C)C(C)(C)C)C(C=O)(CC(O)C2=COC=C2)C1C3269.5Semi standard non polar33892256
Cascarillin,1TBDMS,isomer #3CC(=O)OC1CC2(C)C(CCC(O)C2(C)O)C(C=O)(CC(O[Si](C)(C)C(C)(C)C)C2=COC=C2)C1C3317.7Semi standard non polar33892256
Cascarillin,2TBDMS,isomer #1CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C(C)(C)C)C2(C)O[Si](C)(C)C(C)(C)C)C(C=O)(CC(O)C2=COC=C2)C1C3475.5Semi standard non polar33892256
Cascarillin,2TBDMS,isomer #2CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C(C)(C)C)C2(C)O)C(C=O)(CC(O[Si](C)(C)C(C)(C)C)C2=COC=C2)C1C3453.1Semi standard non polar33892256
Cascarillin,2TBDMS,isomer #3CC(=O)OC1CC2(C)C(CCC(O)C2(C)O[Si](C)(C)C(C)(C)C)C(C=O)(CC(O[Si](C)(C)C(C)(C)C)C2=COC=C2)C1C3453.1Semi standard non polar33892256
Cascarillin,3TBDMS,isomer #1CC(=O)OC1CC2(C)C(CCC(O[Si](C)(C)C(C)(C)C)C2(C)O[Si](C)(C)C(C)(C)C)C(C=O)(CC(O[Si](C)(C)C(C)(C)C)C2=COC=C2)C1C3669.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cascarillin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-1009000000-86634464ced29d7ac6512017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cascarillin GC-MS (3 TMS) - 70eV, Positivesplash10-0cdi-5320198000-26e269a772d7d764854f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cascarillin 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 - Cascarillin 10V, Positive-QTOFsplash10-052g-0009200000-be2a1bd9ad5ea310e8bb2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cascarillin 20V, Positive-QTOFsplash10-0002-3019000000-7d538a6af9f4798fb3e32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cascarillin 40V, Positive-QTOFsplash10-0002-9045000000-dae0120e98244640a0a92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cascarillin 10V, Negative-QTOFsplash10-0a4i-2009600000-fe11de18189371daa65d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cascarillin 20V, Negative-QTOFsplash10-014i-8019100000-72e5d67a776c02f33e642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cascarillin 40V, Negative-QTOFsplash10-066u-9026000000-dd273a6bb27cabeeffc32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cascarillin 10V, Positive-QTOFsplash10-0089-1019100000-fc4aafaaa0804dbffa4e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cascarillin 20V, Positive-QTOFsplash10-02mr-2019000000-56a2e86b7ba8027777382021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cascarillin 40V, Positive-QTOFsplash10-0ku6-9504000000-f374e0b86aae155767552021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cascarillin 10V, Negative-QTOFsplash10-0a4i-2003900000-f69f2d45ab1c6ec32c012021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cascarillin 20V, Negative-QTOFsplash10-066u-9024000000-27fd02f480488c05f9e22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cascarillin 40V, Negative-QTOFsplash10-014i-4093000000-06ed3cc4320904ca40742021-09-23Wishart 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 IDFDB015787
KNApSAcK IDC00003412
Chemspider ID4264331
KEGG Compound IDC09071
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5088211
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1857441
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.