Record Information
Version1.0
Creation date2010-04-08 22:11:57 UTC
Update date2018-05-29 01:20:27 UTC
Primary IDFDB015618
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCostunolide
DescriptionConstituent of costus root (Saussurea lappa). Costunolide is found in tarragon, sweet bay, and herbs and spices.
CAS Number553-21-9
Structure
Thumb
Synonyms
SynonymSource
CostunlideHMDB
CostunolidHMDB
Costus lactoneHMDB
IsocostunolideMeSH
CostunolideMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.097 g/LALOGPS
logP4.22ALOGPS
logP3.82ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity69.95 m³·mol⁻¹ChemAxon
Polarizability26.38 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H20O2
IUPAC name6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one
InChI IdentifierInChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5-,11-9-
InChI KeyHRYLQFBHBWLLLL-GYIATTAWSA-N
Isomeric SMILESC\C1=C\CC\C(C)=C/C2OC(=O)C(=C)C2CC1
Average Molecular Weight232.3181
Monoisotopic Molecular Weight232.146329884
Classification
Description belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGermacranolides and derivatives
Alternative Parents
Substituents
  • Germacranolide
  • Germacrane sesquiterpenoid
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 77.55%; H 8.68%; O 13.77%DFC
Melting PointMp 106-107°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +128 (c, 0.45 in CHCl3)DFC
Spectroscopic UV Data[neutral] lmax 204 (e 18800) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-4920000000-4e64fd5fdc43499db09cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0390000000-90b5c48b328b46f82204View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qi-1930000000-6cfdc6b5c84eab2f9f7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0mi6-9710000000-ddda69ef8cc562458ad9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0290000000-07ab038b28845f8d64a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-0790000000-f2b3e216b0db2d7a4dcaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-5900000000-157775eb321e2f75fa2dView in MoNA
ChemSpider ID4519051
ChEMBL IDNot Available
KEGG Compound IDC09382
Pubchem Compound ID5367559
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36688
CRC / DFC (Dictionary of Food Compounds) IDKDX18-U:KDX19-V
EAFUS IDNot Available
Dr. Duke IDCOSTUNOLIDE
BIGG IDNot Available
KNApSAcK IDC00003240
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti angiogenic48422 An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.DUKE
anti mutagenicDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
dermatitigenicDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
schistosomicideDUKE
trematodicideDUKE
VEGF inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.