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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:26:28 UTC
Update Date2022-03-07 02:55:39 UTC
HMDB IDHMDB0038158
Secondary Accession Numbers
  • HMDB38158
Metabolite Identification
Common NameJangomolide
DescriptionJangomolide, also known as acidissimin?, belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. Jangomolide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863149
Synonyms
ValueSource
Acidissimin?HMDB
Chemical FormulaC26H28O8
Average Molecular Weight468.4957
Monoisotopic Molecular Weight468.178417872
IUPAC Name(2S,7R,13R,14R,16S,19R,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-6,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docos-3-ene-5,12,17-trione
Traditional Name(2S,7R,13R,14R,16S,19R,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-6,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docos-3-ene-5,12,17-trione
CAS Registry Number93767-25-0
SMILES
[H][C@]12OC(C)(C)C3CC(=O)[C@]4(C)C(CC[C@@]5(C)[C@@H](OC(=O)[C@H]6O[C@@]456)C4=COC=C4)[C@]13C=CC(=O)O2
InChI Identifier
InChI=1S/C26H28O8/c1-22(2)15-11-16(27)24(4)14(25(15)9-6-17(28)31-21(25)34-22)5-8-23(3)18(13-7-10-30-12-13)32-20(29)19-26(23,24)33-19/h6-7,9-10,12,14-15,18-19,21H,5,8,11H2,1-4H3/t14?,15?,18-,19+,21-,23-,24-,25-,26+/m0/s1
InChI KeyZYPFSBYGJYBBBK-GLEICTKYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentSteroid lactones
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point282 - 288 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.049 g/LALOGPS
logP3.6ALOGPS
logP3.4ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)17.28ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area104.57 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity115.48 m³·mol⁻¹ChemAxon
Polarizability46.76 ųChemAxon
Number of Rings7ChemAxon
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]+205.69331661259
DarkChem[M-H]-198.49231661259
DeepCCS[M-2H]-246.39930932474
DeepCCS[M+Na]+220.58730932474
AllCCS[M+H]+208.032859911
AllCCS[M+H-H2O]+206.032859911
AllCCS[M+NH4]+210.032859911
AllCCS[M+Na]+210.532859911
AllCCS[M-H]-213.332859911
AllCCS[M+Na-2H]-214.132859911
AllCCS[M+HCOO]-215.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Jangomolide[H][C@]12OC(C)(C)C3CC(=O)[C@]4(C)C(CC[C@@]5(C)[C@@H](OC(=O)[C@H]6O[C@@]456)C4=COC=C4)[C@]13C=CC(=O)O24542.1Standard polar33892256
Jangomolide[H][C@]12OC(C)(C)C3CC(=O)[C@]4(C)C(CC[C@@]5(C)[C@@H](OC(=O)[C@H]6O[C@@]456)C4=COC=C4)[C@]13C=CC(=O)O23202.0Standard non polar33892256
Jangomolide[H][C@]12OC(C)(C)C3CC(=O)[C@]4(C)C(CC[C@@]5(C)[C@@H](OC(=O)[C@H]6O[C@@]456)C4=COC=C4)[C@]13C=CC(=O)O24004.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Jangomolide,1TMS,isomer #1CC1(C)O[C@@H]2OC(=O)C=C[C@]23C1C=C(O[Si](C)(C)C)[C@]1(C)C3CC[C@@]2(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@]3213506.4Semi standard non polar33892256
Jangomolide,1TMS,isomer #1CC1(C)O[C@@H]2OC(=O)C=C[C@]23C1C=C(O[Si](C)(C)C)[C@]1(C)C3CC[C@@]2(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@]3213306.8Standard non polar33892256
Jangomolide,1TBDMS,isomer #1CC1(C)O[C@@H]2OC(=O)C=C[C@]23C1C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)C3CC[C@@]2(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@]3213752.5Semi standard non polar33892256
Jangomolide,1TBDMS,isomer #1CC1(C)O[C@@H]2OC(=O)C=C[C@]23C1C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)C3CC[C@@]2(C)[C@H](C3=COC=C3)OC(=O)[C@H]3O[C@]3213517.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Jangomolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-05c6-9081700000-9451d0e57231b33220de2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Jangomolide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Jangomolide 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 - Jangomolide 10V, Positive-QTOFsplash10-014i-0000900000-394c01972bee2847662f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Jangomolide 20V, Positive-QTOFsplash10-0uxr-0021900000-16ed103be1627e601fa32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Jangomolide 40V, Positive-QTOFsplash10-0k92-9220100000-fb8f52c0a64fefda92652016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Jangomolide 10V, Negative-QTOFsplash10-00xr-0001900000-2fb85c8f2b70c01627e72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Jangomolide 20V, Negative-QTOFsplash10-00r2-1004900000-c3e7d6f4909412c61c722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Jangomolide 40V, Negative-QTOFsplash10-0fr7-6109100000-1ce39415661a81da41aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Jangomolide 10V, Negative-QTOFsplash10-014i-0000900000-2e2e8c33baf90706eda32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Jangomolide 20V, Negative-QTOFsplash10-014i-0000900000-9ae8fb3b0053440d9ef32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Jangomolide 40V, Negative-QTOFsplash10-014i-0010900000-d39d23d8db1f592fe18c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Jangomolide 10V, Positive-QTOFsplash10-014i-0000900000-4e060ec4d7c659bbb78a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Jangomolide 20V, Positive-QTOFsplash10-014i-0001900000-83bd2d7ff966b3c733832021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Jangomolide 40V, Positive-QTOFsplash10-0gw0-1252900000-2594692411ba1880d3532021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB017387
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.