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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:44:44 UTC
Update Date2022-03-07 02:53:56 UTC
HMDB IDHMDB0033972
Secondary Accession Numbers
  • HMDB33972
Metabolite Identification
Common NameAsacoumarin A
DescriptionAsacoumarin A belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a small amount of articles have been published on Asacoumarin A.
Structure
Data?1563862489
SynonymsNot Available
Chemical FormulaC24H30O5
Average Molecular Weight398.492
Monoisotopic Molecular Weight398.20932407
IUPAC Name7-{[(2E,6Z)-5,8-dihydroxy-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy}-2H-chromen-2-one
Traditional Name7-{[(2E,6Z)-5,8-dihydroxy-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy}chromen-2-one
CAS Registry Number122617-02-1
SMILES
CC(C)=CCC(O)C(\C)=C/C(O)C\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C1
InChI Identifier
InChI=1S/C24H30O5/c1-16(2)5-9-22(26)18(4)14-20(25)13-17(3)11-12-28-21-8-6-19-7-10-24(27)29-23(19)15-21/h5-8,10-11,14-15,20,22,25-26H,9,12-13H2,1-4H3/b17-11+,18-14-
InChI KeyNFXNEAJDYTXPLG-FPMGOWAVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Sesquiterpenoid
  • Farsesane sesquiterpenoid
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Fatty alcohol
  • Pyranone
  • Alkyl aryl ether
  • Benzenoid
  • Fatty acyl
  • Pyran
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.089 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0042 g/LALOGPS
logP3.93ALOGPS
logP3.84ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)14.36ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity117.77 m³·mol⁻¹ChemAxon
Polarizability44.72 ųChemAxon
Number of Rings2ChemAxon
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]+194.72131661259
DarkChem[M-H]-197.56831661259
DeepCCS[M+H]+202.4830932474
DeepCCS[M-H]-200.12230932474
DeepCCS[M-2H]-233.75630932474
DeepCCS[M+Na]+208.98530932474
AllCCS[M+H]+202.432859911
AllCCS[M+H-H2O]+200.032859911
AllCCS[M+NH4]+204.732859911
AllCCS[M+Na]+205.432859911
AllCCS[M-H]-201.132859911
AllCCS[M+Na-2H]-201.732859911
AllCCS[M+HCOO]-202.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Asacoumarin ACC(C)=CCC(O)C(\C)=C/C(O)C\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C14275.3Standard polar33892256
Asacoumarin ACC(C)=CCC(O)C(\C)=C/C(O)C\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C13187.0Standard non polar33892256
Asacoumarin ACC(C)=CCC(O)C(\C)=C/C(O)C\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C13427.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Asacoumarin A,1TMS,isomer #1CC(C)=CCC(O[Si](C)(C)C)/C(C)=C\C(O)C/C(C)=C/COC1=CC=C2C=CC(=O)OC2=C13386.4Semi standard non polar33892256
Asacoumarin A,1TMS,isomer #2CC(C)=CCC(O)/C(C)=C\C(C/C(C)=C/COC1=CC=C2C=CC(=O)OC2=C1)O[Si](C)(C)C3358.0Semi standard non polar33892256
Asacoumarin A,2TMS,isomer #1CC(C)=CCC(O[Si](C)(C)C)/C(C)=C\C(C/C(C)=C/COC1=CC=C2C=CC(=O)OC2=C1)O[Si](C)(C)C3319.3Semi standard non polar33892256
Asacoumarin A,1TBDMS,isomer #1CC(C)=CCC(O[Si](C)(C)C(C)(C)C)/C(C)=C\C(O)C/C(C)=C/COC1=CC=C2C=CC(=O)OC2=C13602.8Semi standard non polar33892256
Asacoumarin A,1TBDMS,isomer #2CC(C)=CCC(O)/C(C)=C\C(C/C(C)=C/COC1=CC=C2C=CC(=O)OC2=C1)O[Si](C)(C)C(C)(C)C3583.4Semi standard non polar33892256
Asacoumarin A,2TBDMS,isomer #1CC(C)=CCC(O[Si](C)(C)C(C)(C)C)/C(C)=C\C(C/C(C)=C/COC1=CC=C2C=CC(=O)OC2=C1)O[Si](C)(C)C(C)(C)C3735.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Asacoumarin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ls-8889000000-b4dc1bc07d2d87b62aad2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Asacoumarin A GC-MS (2 TMS) - 70eV, Positivesplash10-00b9-9232650000-80b1202b61b58d7732952017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Asacoumarin A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Asacoumarin A 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 - Asacoumarin A 10V, Positive-QTOFsplash10-01q9-0229000000-98a7c3168513c33209a02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asacoumarin A 20V, Positive-QTOFsplash10-03yr-1985000000-90727c14b874730cdc4e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asacoumarin A 40V, Positive-QTOFsplash10-0400-6930000000-45e41672deee17938f882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asacoumarin A 10V, Negative-QTOFsplash10-0002-0309000000-e3e6565f40a095a1aeef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asacoumarin A 20V, Negative-QTOFsplash10-03di-0913000000-8e90fa7200fca0dc7c0c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asacoumarin A 40V, Negative-QTOFsplash10-02t9-1900000000-34673a10e8028f8c7c3d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asacoumarin A 10V, Negative-QTOFsplash10-03dj-0409000000-6451e2be12d4baa73dcd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asacoumarin A 20V, Negative-QTOFsplash10-03di-0901000000-ec0cb9251228784f9c692021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asacoumarin A 40V, Negative-QTOFsplash10-0159-0900000000-2230d03754e361bd99432021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asacoumarin A 10V, Positive-QTOFsplash10-03di-0339000000-50247d122c277c3c68b02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asacoumarin A 20V, Positive-QTOFsplash10-03di-4937000000-ce747849468e7924d4532021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asacoumarin A 40V, Positive-QTOFsplash10-03dl-8943000000-0a203c1095e840d5af152021-09-24Wishart 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 IDFDB012203
KNApSAcK IDC00053921
Chemspider ID35013681
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751507
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1839541
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.