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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:18:08 UTC
Update Date2022-03-07 02:55:10 UTC
HMDB IDHMDB0037059
Secondary Accession Numbers
  • HMDB37059
Metabolite Identification
Common Name1alpha-Hydroxyarbusculin A
Description1alpha-Hydroxyarbusculin A belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Based on a literature review a small amount of articles have been published on 1alpha-Hydroxyarbusculin A.
Structure
Data?1563862970
Synonyms
ValueSource
1a-Hydroxyarbusculin aGenerator
1Α-hydroxyarbusculin aGenerator
1beta-Hydroxyarbusculin aHMDB
[3AS-(3aalpha,5abeta,6beta,9alpha,9aalpha,9bbeta)]-decahydro-6,9-dihydroxy-5a,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2(3H)-oneHMDB
Chemical FormulaC15H22O4
Average Molecular Weight266.3328
Monoisotopic Molecular Weight266.151809192
IUPAC Name6,9-dihydroxy-5a,9-dimethyl-3-methylidene-dodecahydronaphtho[1,2-b]furan-2-one
Traditional Name6,9-dihydroxy-5a,9-dimethyl-3-methylidene-octahydronaphtho[1,2-b]furan-2-one
CAS Registry Number50301-94-5
SMILES
CC1(O)CCC(O)C2(C)CCC3C(OC(=O)C3=C)C12
InChI Identifier
InChI=1S/C15H22O4/c1-8-9-4-6-14(2)10(16)5-7-15(3,18)12(14)11(9)19-13(8)17/h9-12,16,18H,1,4-7H2,2-3H3
InChI KeyLVABKRFKENTQBT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentEudesmanolides, secoeudesmanolides, and derivatives
Alternative Parents
Substituents
  • Eudesmanolide
  • Sesquiterpenoid
  • Naphthofuran
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tertiary alcohol
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • 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 Point194 - 196 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4602 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.68 g/LALOGPS
logP0.98ALOGPS
logP1.2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)14.38ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity69.52 m³·mol⁻¹ChemAxon
Polarizability28.76 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]+161.07131661259
DarkChem[M-H]-156.51931661259
DeepCCS[M-2H]-199.66130932474
DeepCCS[M+Na]+175.22630932474
AllCCS[M+H]+163.132859911
AllCCS[M+H-H2O]+159.632859911
AllCCS[M+NH4]+166.432859911
AllCCS[M+Na]+167.332859911
AllCCS[M-H]-167.532859911
AllCCS[M+Na-2H]-167.532859911
AllCCS[M+HCOO]-167.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1alpha-Hydroxyarbusculin ACC1(O)CCC(O)C2(C)CCC3C(OC(=O)C3=C)C123367.0Standard polar33892256
1alpha-Hydroxyarbusculin ACC1(O)CCC(O)C2(C)CCC3C(OC(=O)C3=C)C122193.4Standard non polar33892256
1alpha-Hydroxyarbusculin ACC1(O)CCC(O)C2(C)CCC3C(OC(=O)C3=C)C122397.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1alpha-Hydroxyarbusculin A,1TMS,isomer #1C=C1C(=O)OC2C1CCC1(C)C(O)CCC(C)(O[Si](C)(C)C)C212306.0Semi standard non polar33892256
1alpha-Hydroxyarbusculin A,1TMS,isomer #2C=C1C(=O)OC2C1CCC1(C)C(O[Si](C)(C)C)CCC(C)(O)C212317.0Semi standard non polar33892256
1alpha-Hydroxyarbusculin A,2TMS,isomer #1C=C1C(=O)OC2C1CCC1(C)C(O[Si](C)(C)C)CCC(C)(O[Si](C)(C)C)C212358.1Semi standard non polar33892256
1alpha-Hydroxyarbusculin A,1TBDMS,isomer #1C=C1C(=O)OC2C1CCC1(C)C(O)CCC(C)(O[Si](C)(C)C(C)(C)C)C212547.2Semi standard non polar33892256
1alpha-Hydroxyarbusculin A,1TBDMS,isomer #2C=C1C(=O)OC2C1CCC1(C)C(O[Si](C)(C)C(C)(C)C)CCC(C)(O)C212551.1Semi standard non polar33892256
1alpha-Hydroxyarbusculin A,2TBDMS,isomer #1C=C1C(=O)OC2C1CCC1(C)C(O[Si](C)(C)C(C)(C)C)CCC(C)(O[Si](C)(C)C(C)(C)C)C212803.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1alpha-Hydroxyarbusculin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pdj-6790000000-35e83f4787788e5fc54b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1alpha-Hydroxyarbusculin A GC-MS (2 TMS) - 70eV, Positivesplash10-0092-3149000000-348c8fa6ca0fc4c62e5b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1alpha-Hydroxyarbusculin 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 - 1alpha-Hydroxyarbusculin A 10V, Positive-QTOFsplash10-00kb-0190000000-c4950747fd8d4a11cae42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1alpha-Hydroxyarbusculin A 20V, Positive-QTOFsplash10-0032-0790000000-02e8098eca7f8ba4b1d72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1alpha-Hydroxyarbusculin A 40V, Positive-QTOFsplash10-0f7o-9820000000-48982c141ae5cc18cf642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1alpha-Hydroxyarbusculin A 10V, Negative-QTOFsplash10-014i-0090000000-ceb1483d126a8d10f1752016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1alpha-Hydroxyarbusculin A 20V, Negative-QTOFsplash10-00r2-0190000000-ca90e05e632fc12484762016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1alpha-Hydroxyarbusculin A 40V, Negative-QTOFsplash10-0udj-9640000000-4a9e7ba8051436fd30d62016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1alpha-Hydroxyarbusculin A 10V, Negative-QTOFsplash10-014i-0090000000-c6cc318d73093d1123732021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1alpha-Hydroxyarbusculin A 20V, Negative-QTOFsplash10-014i-0190000000-1cee06f3cbcf6c001b912021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1alpha-Hydroxyarbusculin A 40V, Negative-QTOFsplash10-03di-4920000000-aafeb32f74732e424ca52021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1alpha-Hydroxyarbusculin A 10V, Positive-QTOFsplash10-014i-0090000000-8b4925e62538a47e11052021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1alpha-Hydroxyarbusculin A 20V, Positive-QTOFsplash10-014i-0490000000-6740fed5dc794fad2e692021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1alpha-Hydroxyarbusculin A 40V, Positive-QTOFsplash10-01b9-3910000000-b8f677e6c9eabb005a2c2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 IDFDB016042
KNApSAcK IDC00013003
Chemspider ID35014363
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74426514
PDB IDNot Available
ChEBI ID174512
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1859031
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.