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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:00:49 UTC
Update Date2022-03-07 02:54:43 UTC
HMDB IDHMDB0035960
Secondary Accession Numbers
  • HMDB35960
Metabolite Identification
Common NameMasticadienediol
DescriptionMasticadienediol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Masticadienediol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862799
SynonymsNot Available
Chemical FormulaC30H50O2
Average Molecular Weight442.7168
Monoisotopic Molecular Weight442.381080844
IUPAC Name14-[(5Z)-7-hydroxy-6-methylhept-5-en-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol
Traditional Name14-[(5Z)-7-hydroxy-6-methylhept-5-en-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol
CAS Registry Number6138-94-9
SMILES
CC(CC\C=C(\C)CO)C1CCC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3CCC12C
InChI Identifier
InChI=1S/C30H50O2/c1-20(19-31)9-8-10-21(2)22-13-17-30(7)24-11-12-25-27(3,4)26(32)15-16-28(25,5)23(24)14-18-29(22,30)6/h9,11,21-23,25-26,31-32H,8,10,12-19H2,1-7H3/b20-9-
InChI KeyWCSYVWJCJYEXKL-UKWGHVSLSA-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
  • 26-hydroxysteroid
  • Dihydroxy bile acid, alcohol, or derivatives
  • Cholane-skeleton
  • Hydroxy bile acid, alcohol, or derivatives
  • Bile acid, alcohol, or derivatives
  • 3-hydroxy-delta-7-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • Delta-7-steroid
  • Steroid
  • Fatty alcohol
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point186 - 187 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00038 g/LALOGPS
logP7.3ALOGPS
logP6.47ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)16.64ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity136.59 m³·mol⁻¹ChemAxon
Polarizability55 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+203.31731661259
DarkChem[M-H]-198.25631661259
DeepCCS[M-2H]-242.19130932474
DeepCCS[M+Na]+217.41830932474
AllCCS[M+H]+216.032859911
AllCCS[M+H-H2O]+214.232859911
AllCCS[M+NH4]+217.732859911
AllCCS[M+Na]+218.132859911
AllCCS[M-H]-212.732859911
AllCCS[M+Na-2H]-215.132859911
AllCCS[M+HCOO]-217.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MasticadienediolCC(CC\C=C(\C)CO)C1CCC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3CCC12C3024.1Standard polar33892256
MasticadienediolCC(CC\C=C(\C)CO)C1CCC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3CCC12C3499.6Standard non polar33892256
MasticadienediolCC(CC\C=C(\C)CO)C1CCC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3CCC12C3666.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Masticadienediol,1TMS,isomer #1C/C(=C/CCC(C)C1CCC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3CCC12C)CO[Si](C)(C)C3686.8Semi standard non polar33892256
Masticadienediol,1TMS,isomer #2C/C(=C/CCC(C)C1CCC2(C)C3=CCC4C(C)(C)C(O[Si](C)(C)C)CCC4(C)C3CCC12C)CO3661.9Semi standard non polar33892256
Masticadienediol,2TMS,isomer #1C/C(=C/CCC(C)C1CCC2(C)C3=CCC4C(C)(C)C(O[Si](C)(C)C)CCC4(C)C3CCC12C)CO[Si](C)(C)C3698.9Semi standard non polar33892256
Masticadienediol,1TBDMS,isomer #1C/C(=C/CCC(C)C1CCC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3CCC12C)CO[Si](C)(C)C(C)(C)C3915.5Semi standard non polar33892256
Masticadienediol,1TBDMS,isomer #2C/C(=C/CCC(C)C1CCC2(C)C3=CCC4C(C)(C)C(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C)CO3883.8Semi standard non polar33892256
Masticadienediol,2TBDMS,isomer #1C/C(=C/CCC(C)C1CCC2(C)C3=CCC4C(C)(C)C(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C)CO[Si](C)(C)C(C)(C)C4144.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Masticadienediol GC-MS (Non-derivatized) - 70eV, Positivesplash10-01t9-1015900000-dc4bc83722e9959f6ba82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Masticadienediol GC-MS (2 TMS) - 70eV, Positivesplash10-00di-1202390000-06cee5e128df3c5d35452017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Masticadienediol 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 - Masticadienediol 10V, Positive-QTOFsplash10-004l-0001900000-df2ac2a1a8c67136f68a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masticadienediol 20V, Positive-QTOFsplash10-056r-3109700000-1e542803b5508f88804d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masticadienediol 40V, Positive-QTOFsplash10-0ukc-5339100000-7ded7b12a235d29ec73f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masticadienediol 10V, Negative-QTOFsplash10-0006-0000900000-72bd8795c5514ca5032c2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masticadienediol 20V, Negative-QTOFsplash10-006x-0001900000-ab31109c11087d843aef2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masticadienediol 40V, Negative-QTOFsplash10-054k-4009700000-0e24fc282c36ade553c02016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masticadienediol 10V, Negative-QTOFsplash10-0006-0000900000-6d6bd12b7c356ba62f302021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masticadienediol 20V, Negative-QTOFsplash10-01ox-0000900000-77d4ca51cd750e4069382021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masticadienediol 40V, Negative-QTOFsplash10-08g1-2006900000-e803b675a7709c5946252021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masticadienediol 10V, Positive-QTOFsplash10-0a4j-9802500000-0aa6f3c609c506b07cd82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masticadienediol 20V, Positive-QTOFsplash10-0aos-9124000000-aa21dd6151b242c7fcf82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masticadienediol 40V, Positive-QTOFsplash10-0ll1-9624000000-08a7f88ed4b423b358b22021-09-24Wishart 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 IDFDB014764
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751887
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.