Crispane (CHEM032046)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:06:19 UTC
Update Date2016-11-09 01:19:23 UTC
Accession NumberCHEM032046
Identification
Common NameCrispane
ClassSmall Molecule
DescriptionCrispane is found in herbs and spices. Crispane is isolated from Lasianthaea fruticosa and parsley Petroselinum crispum [DFC] (Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Lasidiol angelateHMDB
(1S,2S,4AS,8as)-1-hydroxy-4,4a-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoic acidGenerator
Chemical FormulaC20H32O3
Average Molecular Mass320.466 g/mol
Monoisotopic Mass320.235 g/mol
CAS Registry Number79803-28-4
IUPAC Name(1S,2S,4aS,8aS)-1-hydroxy-4,4a-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate
Traditional Name(1S,2S,4aS,8aS)-1-hydroxy-1-isopropyl-4,4a-dimethyl-2,5,6,7,8,8a-hexahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate
SMILESC\C=C(\C)C(=O)O[C@H]1C=C(C)[C@@]2(C)CCCC[C@]2([H])[C@@]1(O)C(C)C
InChI IdentifierInChI=1S/C20H32O3/c1-7-14(4)18(21)23-17-12-15(5)19(6)11-9-8-10-16(19)20(17,22)13(2)3/h7,12-13,16-17,22H,8-11H2,1-6H3/b14-7-/t16-,17-,19+,20-/m0/s1
InChI KeyNXPBEWQMSGGADR-XUDYDAPFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
  • P-menthane monoterpenoid
  • Fatty acid ester
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.027 g/LALOGPS
logP5.11ALOGPS
logP5ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)13.36ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.24 m³·mol⁻¹ChemAxon
Polarizability37.59 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0apl-9661000000-40798404c21d20d6c988Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-003i-9223000000-cbc19ddf0aa671e2e368Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-4069000000-086da4dc42f6dfa48abcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05cr-9341000000-ad40b508cb017475ad4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9300000000-0ee2672415ed82dd8444Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2019000000-e083695596a980227af4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-9276000000-134891071ed41a12727cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-9320000000-df24fb905c0d22cf11d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0069000000-dd3af3f1297a91da5f87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aba-9220000000-a000e9bcb045081e5577Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-9100000000-c2e115c8e3326772edc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1029000000-639bcfdbab273bfa3250Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-9071000000-56446b88a10ea7a11c0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05i0-2390000000-43b28025e17d012b9d5aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0038694
FooDB IDFDB018099
Phenol Explorer IDNot Available
KNApSAcK IDC00031523
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30777287
ChEBI ID175103
PubChem Compound ID131752434
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Appendino G, Jakupovic J, Bossio E: Structural revision of the parsley sesquiterpenes crispanone and crispane. Phytochemistry. 1998 Nov 20;49(6):1719-1722.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. 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.
4. 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.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
7. The lipid handbook with CD-ROM