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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:51:16 UTC
Update Date2022-03-07 02:55:01 UTC
HMDB IDHMDB0036688
Secondary Accession Numbers
  • HMDB36688
Metabolite Identification
Common NameCostunolide
DescriptionCostunolide 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. Based on a literature review a small amount of articles have been published on Costunolide.
Structure
Data?1563862909
Synonyms
ValueSource
CostunlideHMDB
CostunolidHMDB
Costus lactoneHMDB
IsocostunolideMeSH
CostunolideMeSH
Chemical FormulaC15H20O2
Average Molecular Weight232.3181
Monoisotopic Molecular Weight232.146329884
IUPAC Name6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one
Traditional Name6,10-dimethyl-3-methylidene-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one
CAS Registry Number553-21-9
SMILES
C\C1=C\CC\C(C)=C/C2OC(=O)C(=C)C2CC1
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point106 - 107 °CNot Available
Boiling Point205.00 to 211.00 °C. @ 13.00 mm HgThe Good Scents Company Information System
Water Solubility9.38 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.049 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+157.01931661259
DarkChem[M-H]-150.5731661259
DeepCCS[M+H]+161.46130932474
DeepCCS[M-H]-159.10330932474
DeepCCS[M-2H]-192.02730932474
DeepCCS[M+Na]+167.55430932474
AllCCS[M+H]+154.532859911
AllCCS[M+H-H2O]+150.532859911
AllCCS[M+NH4]+158.232859911
AllCCS[M+Na]+159.332859911
AllCCS[M-H]-159.932859911
AllCCS[M+Na-2H]-160.132859911
AllCCS[M+HCOO]-160.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CostunolideC\C1=C\CC\C(C)=C/C2OC(=O)C(=C)C2CC12485.0Standard polar33892256
CostunolideC\C1=C\CC\C(C)=C/C2OC(=O)C(=C)C2CC11854.9Standard non polar33892256
CostunolideC\C1=C\CC\C(C)=C/C2OC(=O)C(=C)C2CC11998.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Costunolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-4920000000-4e64fd5fdc43499db09c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Costunolide 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 - Costunolide 10V, Positive-QTOFsplash10-001i-0390000000-90b5c48b328b46f822042016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Costunolide 20V, Positive-QTOFsplash10-01qi-1930000000-6cfdc6b5c84eab2f9f7d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Costunolide 40V, Positive-QTOFsplash10-0mi6-9710000000-ddda69ef8cc562458ad92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Costunolide 10V, Negative-QTOFsplash10-001i-0290000000-07ab038b28845f8d64a12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Costunolide 20V, Negative-QTOFsplash10-001r-0790000000-f2b3e216b0db2d7a4dca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Costunolide 40V, Negative-QTOFsplash10-000i-5900000000-157775eb321e2f75fa2d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Costunolide 10V, Negative-QTOFsplash10-001i-0090000000-403b175a8d75af9b9dc42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Costunolide 20V, Negative-QTOFsplash10-001i-0390000000-16fbf014b5978f284c852021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Costunolide 40V, Negative-QTOFsplash10-01b9-9500000000-2ce7ff1d0912ac2d90ee2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Costunolide 10V, Positive-QTOFsplash10-001i-0190000000-c5e9a61d3011edbf30f32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Costunolide 20V, Positive-QTOFsplash10-001r-0980000000-0a8be66862e84091d6a42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Costunolide 40V, Positive-QTOFsplash10-0a4i-0900000000-9eaa625d0c4efee677912021-09-25Wishart 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 IDFDB015618
KNApSAcK IDC00003240
Chemspider ID4519051
KEGG Compound IDC09382
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCostunolide
METLIN IDNot Available
PubChem Compound5367559
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1016401
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lee MG, Lee KT, Chi SG, Park JH: Costunolide induces apoptosis by ROS-mediated mitochondrial permeability transition and cytochrome C release. Biol Pharm Bull. 2001 Mar;24(3):303-6. [PubMed:11256490 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.