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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:17:54 UTC
Update Date2022-03-07 02:55:10 UTC
HMDB IDHMDB0037055
Secondary Accession Numbers
  • HMDB37055
Metabolite Identification
Common NameIstanbulin A
DescriptionIstanbulin 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 significant number of articles have been published on Istanbulin A.
Structure
Data?1563862970
Synonyms
ValueSource
ent-8a-Hydroxy-1-oxo-7(11)-eremophilen-12,8-olideHMDB
Istanbulin-aHMDB, MeSH
Istanbulin aMeSH
Chemical FormulaC15H20O4
Average Molecular Weight264.3169
Monoisotopic Molecular Weight264.136159128
IUPAC Name9a-hydroxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2,8-dione
Traditional Name9a-hydroxy-3,4a,5-trimethyl-4H,5H,6H,7H,8aH,9H-naphtho[2,3-b]furan-2,8-dione
CAS Registry Number35481-83-5
SMILES
CC1CCC(=O)C2CC3(O)OC(=O)C(C)=C3CC12C
InChI Identifier
InChI=1S/C15H20O4/c1-8-4-5-12(16)11-7-15(18)10(6-14(8,11)3)9(2)13(17)19-15/h8,11,18H,4-7H2,1-3H3
InChI KeyHYBIDSYXKTYHCM-UHFFFAOYSA-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
  • Eremophilanolide or secoeremophilanolide
  • Sesquiterpenoid
  • Naphthofuran
  • 2-furanone
  • Cyclic alcohol
  • Dihydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Lactone
  • Ketone
  • Hemiacetal
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • 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 Point246 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1013 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.89 g/LALOGPS
logP1.82ALOGPS
logP2.34ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)11.24ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity69.39 m³·mol⁻¹ChemAxon
Polarizability27.88 ųChemAxon
Number of Rings3ChemAxon
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]+162.56631661259
DarkChem[M-H]-155.60331661259
DeepCCS[M-2H]-193.17630932474
DeepCCS[M+Na]+168.59530932474
AllCCS[M+H]+161.132859911
AllCCS[M+H-H2O]+157.532859911
AllCCS[M+NH4]+164.432859911
AllCCS[M+Na]+165.432859911
AllCCS[M-H]-167.532859911
AllCCS[M+Na-2H]-167.432859911
AllCCS[M+HCOO]-167.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Istanbulin ACC1CCC(=O)C2CC3(O)OC(=O)C(C)=C3CC12C3381.9Standard polar33892256
Istanbulin ACC1CCC(=O)C2CC3(O)OC(=O)C(C)=C3CC12C2130.0Standard non polar33892256
Istanbulin ACC1CCC(=O)C2CC3(O)OC(=O)C(C)=C3CC12C2301.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Istanbulin A,1TMS,isomer #1CC1=C2CC3(C)C(C)CCC(=O)C3CC2(O[Si](C)(C)C)OC1=O2294.3Semi standard non polar33892256
Istanbulin A,1TMS,isomer #2CC1=C2CC3(C)C(=C(O[Si](C)(C)C)CCC3C)CC2(O)OC1=O2292.3Semi standard non polar33892256
Istanbulin A,1TMS,isomer #3CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C)C3CC2(O)OC1=O2250.9Semi standard non polar33892256
Istanbulin A,2TMS,isomer #1CC1=C2CC3(C)C(=C(O[Si](C)(C)C)CCC3C)CC2(O[Si](C)(C)C)OC1=O2386.2Semi standard non polar33892256
Istanbulin A,2TMS,isomer #1CC1=C2CC3(C)C(=C(O[Si](C)(C)C)CCC3C)CC2(O[Si](C)(C)C)OC1=O2257.7Standard non polar33892256
Istanbulin A,2TMS,isomer #2CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C)C3CC2(O[Si](C)(C)C)OC1=O2364.9Semi standard non polar33892256
Istanbulin A,2TMS,isomer #2CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C)C3CC2(O[Si](C)(C)C)OC1=O2172.6Standard non polar33892256
Istanbulin A,1TBDMS,isomer #1CC1=C2CC3(C)C(C)CCC(=O)C3CC2(O[Si](C)(C)C(C)(C)C)OC1=O2524.1Semi standard non polar33892256
Istanbulin A,1TBDMS,isomer #2CC1=C2CC3(C)C(=C(O[Si](C)(C)C(C)(C)C)CCC3C)CC2(O)OC1=O2512.5Semi standard non polar33892256
Istanbulin A,1TBDMS,isomer #3CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C(C)(C)C)C3CC2(O)OC1=O2470.2Semi standard non polar33892256
Istanbulin A,2TBDMS,isomer #1CC1=C2CC3(C)C(=C(O[Si](C)(C)C(C)(C)C)CCC3C)CC2(O[Si](C)(C)C(C)(C)C)OC1=O2836.5Semi standard non polar33892256
Istanbulin A,2TBDMS,isomer #1CC1=C2CC3(C)C(=C(O[Si](C)(C)C(C)(C)C)CCC3C)CC2(O[Si](C)(C)C(C)(C)C)OC1=O2785.6Standard non polar33892256
Istanbulin A,2TBDMS,isomer #2CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C(C)(C)C)C3CC2(O[Si](C)(C)C(C)(C)C)OC1=O2804.7Semi standard non polar33892256
Istanbulin A,2TBDMS,isomer #2CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C(C)(C)C)C3CC2(O[Si](C)(C)C(C)(C)C)OC1=O2568.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Istanbulin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1960000000-61907d8d15b1cbc582d52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Istanbulin A GC-MS (1 TMS) - 70eV, Positivesplash10-009i-8594000000-e3d285e622927e7448422017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Istanbulin 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 - Istanbulin A 10V, Positive-QTOFsplash10-014i-0390000000-4bbdc72d7be928afeddd2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Istanbulin A 20V, Positive-QTOFsplash10-00ke-2960000000-2441ad518e158dd2ba9f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Istanbulin A 40V, Positive-QTOFsplash10-0k97-9300000000-ea930d4bee3a287122932015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Istanbulin A 10V, Negative-QTOFsplash10-03di-0090000000-ca8ed823a3d7b408e00c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Istanbulin A 20V, Negative-QTOFsplash10-0900-0090000000-2beb80d806f8e4bfb86b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Istanbulin A 40V, Negative-QTOFsplash10-00l6-5690000000-c385f2ffc88d585224782015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Istanbulin A 10V, Negative-QTOFsplash10-03di-0090000000-16d43704d08f3756e03a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Istanbulin A 20V, Negative-QTOFsplash10-03di-0090000000-cf4dd69ba3cf077e83ed2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Istanbulin A 40V, Negative-QTOFsplash10-03ki-2890000000-0da57c6995395368a5c22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Istanbulin A 10V, Positive-QTOFsplash10-014i-0090000000-8d9e65027e815d92f3412021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Istanbulin A 20V, Positive-QTOFsplash10-014i-0290000000-dc1ee00146a9b0d0427c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Istanbulin A 40V, Positive-QTOFsplash10-00si-3920000000-48bfbf4c83ccd0e454ab2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB016038
KNApSAcK IDC00017304
Chemspider ID35014361
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12304519
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1858991
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.