Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:44:41 UTC
Update Date2022-03-07 02:54:58 UTC
HMDB IDHMDB0036587
Secondary Accession Numbers
  • HMDB36587
Metabolite Identification
Common NameQuassin
DescriptionQuassin 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. Based on a literature review a small amount of articles have been published on Quassin.
Structure
Data?1563862893
Synonyms
ValueSource
Nigakilactone DHMDB
QuassinMeSH
Chemical FormulaC22H28O6
Average Molecular Weight388.4541
Monoisotopic Molecular Weight388.188588628
IUPAC Name4,15-dimethoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-4,14-diene-3,11,16-trione
Traditional Namequassin
CAS Registry Number76-78-8
SMILES
COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(=O)C(C34C)C2(C)C1=O
InChI Identifier
InChI=1S/C22H28O6/c1-10-7-14(26-5)20(25)22(4)12(10)8-15-21(3)13(9-16(23)28-15)11(2)18(27-6)17(24)19(21)22/h7,10,12-13,15,19H,8-9H2,1-6H3
InChI KeyIOSXSVZRTUWBHC-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 Parents
Substituents
  • C-20 quassinoid skeleton
  • Quassinoid
  • Naphthopyran
  • Naphthalene
  • Delta valerolactone
  • Cyclohexenone
  • Delta_valerolactone
  • Pyran
  • Oxane
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point221 - 222 °CNot Available
Boiling Point586.30 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility566.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.220 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.043 g/LALOGPS
logP2.73ALOGPS
logP2.24ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)18.08ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity104.2 m³·mol⁻¹ChemAxon
Polarizability41 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]+192.02431661259
DarkChem[M-H]-186.72131661259
DeepCCS[M-2H]-228.90730932474
DeepCCS[M+Na]+204.43230932474
AllCCS[M+H]+190.732859911
AllCCS[M+H-H2O]+188.232859911
AllCCS[M+NH4]+193.032859911
AllCCS[M+Na]+193.732859911
AllCCS[M-H]-197.932859911
AllCCS[M+Na-2H]-198.432859911
AllCCS[M+HCOO]-199.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
QuassinCOC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(=O)C(C34C)C2(C)C1=O3953.9Standard polar33892256
QuassinCOC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(=O)C(C34C)C2(C)C1=O2706.1Standard non polar33892256
QuassinCOC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(=O)C(C34C)C2(C)C1=O3037.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Quassin,1TMS,isomer #1COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(O[Si](C)(C)C)=C(C2(C)C1=O)C34C2949.0Semi standard non polar33892256
Quassin,1TMS,isomer #1COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(O[Si](C)(C)C)=C(C2(C)C1=O)C34C2761.5Standard non polar33892256
Quassin,1TBDMS,isomer #1COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C(C2(C)C1=O)C34C3161.1Semi standard non polar33892256
Quassin,1TBDMS,isomer #1COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C(C2(C)C1=O)C34C2979.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Quassin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0odj-0209000000-e284c8786161fb2c03792017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quassin 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 - Quassin 10V, Positive-QTOFsplash10-000i-0009000000-7e540d032cd53e8bed922015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quassin 20V, Positive-QTOFsplash10-0072-0019000000-17bae020877053ca31602015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quassin 40V, Positive-QTOFsplash10-0udi-9453000000-d49be7bcb435b4da00852015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quassin 10V, Negative-QTOFsplash10-000i-0009000000-9ac13bf543d17c7a8ccd2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quassin 20V, Negative-QTOFsplash10-000l-0009000000-ac85f55d6c57b2e682002015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quassin 40V, Negative-QTOFsplash10-002f-3019000000-c8ca587aaf4c7a6021552015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quassin 10V, Positive-QTOFsplash10-000l-0009000000-7da52e89cb542bda89c42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quassin 20V, Positive-QTOFsplash10-03dr-0029000000-a48b2bc4a57e0ce121302021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quassin 40V, Positive-QTOFsplash10-00n0-3897000000-6f3942b0306db2d2d1252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quassin 10V, Negative-QTOFsplash10-000i-0009000000-7f16ac45973a6479b3e52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quassin 20V, Negative-QTOFsplash10-000i-0009000000-f8847d5c1dba461f6dac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quassin 40V, Negative-QTOFsplash10-0avr-0029000000-d98d24d4098095349f752021-09-23Wishart 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 IDFDB015499
KNApSAcK IDC00003726
Chemspider ID4824
KEGG Compound IDC08778
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQuassin
METLIN IDNot Available
PubChem Compound4998
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1368861
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.