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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:40:56 UTC
Update Date2022-03-07 02:53:54 UTC
HMDB IDHMDB0033907
Secondary Accession Numbers
  • HMDB33907
Metabolite Identification
Common NameHomodolicholide
DescriptionHomodolicholide belongs to the class of organic compounds known as brassinolides and derivatives. These are cholestane based steroid lactones containing benzo[c]indeno[5,4-e]oxepin-3-one. Based on a literature review a small amount of articles have been published on Homodolicholide.
Structure
Data?1563862479
Synonyms
ValueSource
28-HomodolicholideHMDB
2a,3a,22R,23R-Tetrahydroxy-b-homo-7-oxa-5a-stigmast-24(28)-en-6-oneHMDB
Chemical FormulaC29H48O6
Average Molecular Weight492.6878
Monoisotopic Molecular Weight492.345089268
IUPAC Name15-[(5E)-3,4-dihydroxy-5-(propan-2-yl)hept-5-en-2-yl]-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one
Traditional Name15-[(5E)-3,4-dihydroxy-5-isopropylhept-5-en-2-yl]-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one
CAS Registry Number86630-40-2
SMILES
C\C=C(/C(C)C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C
InChI Identifier
InChI=1S/C29H48O6/c1-7-17(15(2)3)26(33)25(32)16(4)19-8-9-20-18-14-35-27(34)22-12-23(30)24(31)13-29(22,6)21(18)10-11-28(19,20)5/h7,15-16,18-26,30-33H,8-14H2,1-6H3/b17-7+
InChI KeyLRRBQWHWKJDDAW-REZTVBANSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as brassinolides and derivatives. These are cholestane based steroid lactones containing benzo[c]indeno[5,4-e]oxepin-3-one.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentBrassinolides and derivatives
Alternative Parents
Substituents
  • Brassinolide-skeleton
  • Caprolactone
  • Oxepane
  • Cyclic alcohol
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • 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 Point227 - 228 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP3.36ALOGPS
logP3.25ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)13.3ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity135.78 m³·mol⁻¹ChemAxon
Polarizability56.41 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+214.82331661259
DarkChem[M-H]-209.3631661259
DeepCCS[M-2H]-251.6830932474
DeepCCS[M+Na]+226.90730932474
AllCCS[M+H]+220.032859911
AllCCS[M+H-H2O]+218.432859911
AllCCS[M+NH4]+221.532859911
AllCCS[M+Na]+221.932859911
AllCCS[M-H]-215.732859911
AllCCS[M+Na-2H]-218.432859911
AllCCS[M+HCOO]-221.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HomodolicholideC\C=C(/C(C)C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C3256.1Standard polar33892256
HomodolicholideC\C=C(/C(C)C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C3398.2Standard non polar33892256
HomodolicholideC\C=C(/C(C)C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C3909.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Homodolicholide,1TMS,isomer #1C/C=C(\C(C)C)C(O[Si](C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C4013.1Semi standard non polar33892256
Homodolicholide,1TMS,isomer #2C/C=C(\C(C)C)C(O)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C3993.3Semi standard non polar33892256
Homodolicholide,1TMS,isomer #3C/C=C(\C(C)C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O)CC4(C)C3CCC12C4042.2Semi standard non polar33892256
Homodolicholide,1TMS,isomer #4C/C=C(\C(C)C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C)CC4(C)C3CCC12C4039.1Semi standard non polar33892256
Homodolicholide,2TMS,isomer #1C/C=C(\C(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C3901.4Semi standard non polar33892256
Homodolicholide,2TMS,isomer #2C/C=C(\C(C)C)C(O[Si](C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O)CC4(C)C3CCC12C3938.1Semi standard non polar33892256
Homodolicholide,2TMS,isomer #3C/C=C(\C(C)C)C(O[Si](C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C)CC4(C)C3CCC12C3922.8Semi standard non polar33892256
Homodolicholide,2TMS,isomer #4C/C=C(\C(C)C)C(O)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O)CC4(C)C3CCC12C3887.4Semi standard non polar33892256
Homodolicholide,2TMS,isomer #5C/C=C(\C(C)C)C(O)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C)CC4(C)C3CCC12C3875.8Semi standard non polar33892256
Homodolicholide,2TMS,isomer #6C/C=C(\C(C)C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O[Si](C)(C)C)CC4(C)C3CCC12C4020.5Semi standard non polar33892256
Homodolicholide,3TMS,isomer #1C/C=C(\C(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O)CC4(C)C3CCC12C3781.4Semi standard non polar33892256
Homodolicholide,3TMS,isomer #2C/C=C(\C(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C)CC4(C)C3CCC12C3772.9Semi standard non polar33892256
Homodolicholide,3TMS,isomer #3C/C=C(\C(C)C)C(O[Si](C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O[Si](C)(C)C)CC4(C)C3CCC12C3853.7Semi standard non polar33892256
Homodolicholide,3TMS,isomer #4C/C=C(\C(C)C)C(O)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O[Si](C)(C)C)CC4(C)C3CCC12C3819.5Semi standard non polar33892256
Homodolicholide,4TMS,isomer #1C/C=C(\C(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O[Si](C)(C)C)CC4(C)C3CCC12C3703.1Semi standard non polar33892256
Homodolicholide,1TBDMS,isomer #1C/C=C(\C(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C4242.4Semi standard non polar33892256
Homodolicholide,1TBDMS,isomer #2C/C=C(\C(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C4231.2Semi standard non polar33892256
Homodolicholide,1TBDMS,isomer #3C/C=C(\C(C)C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C(C)(C)C)C(O)CC4(C)C3CCC12C4264.7Semi standard non polar33892256
Homodolicholide,1TBDMS,isomer #4C/C=C(\C(C)C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C(C)(C)C)CC4(C)C3CCC12C4267.5Semi standard non polar33892256
Homodolicholide,2TBDMS,isomer #1C/C=C(\C(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C4365.5Semi standard non polar33892256
Homodolicholide,2TBDMS,isomer #2C/C=C(\C(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C(C)(C)C)C(O)CC4(C)C3CCC12C4385.4Semi standard non polar33892256
Homodolicholide,2TBDMS,isomer #3C/C=C(\C(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C(C)(C)C)CC4(C)C3CCC12C4374.0Semi standard non polar33892256
Homodolicholide,2TBDMS,isomer #4C/C=C(\C(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C(C)(C)C)C(O)CC4(C)C3CCC12C4352.4Semi standard non polar33892256
Homodolicholide,2TBDMS,isomer #5C/C=C(\C(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C(C)(C)C)CC4(C)C3CCC12C4336.1Semi standard non polar33892256
Homodolicholide,2TBDMS,isomer #6C/C=C(\C(C)C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC4(C)C3CCC12C4466.7Semi standard non polar33892256
Homodolicholide,3TBDMS,isomer #1C/C=C(\C(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C(C)(C)C)C(O)CC4(C)C3CCC12C4453.8Semi standard non polar33892256
Homodolicholide,3TBDMS,isomer #2C/C=C(\C(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C(C)(C)C)CC4(C)C3CCC12C4449.4Semi standard non polar33892256
Homodolicholide,3TBDMS,isomer #3C/C=C(\C(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC4(C)C3CCC12C4506.8Semi standard non polar33892256
Homodolicholide,3TBDMS,isomer #4C/C=C(\C(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC4(C)C3CCC12C4472.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Homodolicholide GC-MS (Non-derivatized) - 70eV, Positivesplash10-00b9-1416900000-16963be285e394e968fc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homodolicholide GC-MS (2 TMS) - 70eV, Positivesplash10-00di-2211439000-7ab1e8d03d8a018d05802017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homodolicholide 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 - Homodolicholide 10V, Positive-QTOFsplash10-002f-0102900000-ec215e68bbbed33ded112016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homodolicholide 20V, Positive-QTOFsplash10-03di-5809600000-b455ff51508939a22f512016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homodolicholide 40V, Positive-QTOFsplash10-03di-6904100000-3cb5a54c467d0f6711ff2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homodolicholide 10V, Negative-QTOFsplash10-0006-0000900000-85e746d73620376620882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homodolicholide 20V, Negative-QTOFsplash10-001i-6204900000-485fab7493388383a0ae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homodolicholide 40V, Negative-QTOFsplash10-001i-9302200000-cafbb2cbc138a12c23e12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homodolicholide 10V, Positive-QTOFsplash10-014j-0003900000-fb5dd67b9a58e5b730732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homodolicholide 20V, Positive-QTOFsplash10-002e-3309200000-f8c518ec2e63140478ab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homodolicholide 40V, Positive-QTOFsplash10-052g-9422000000-406faaa4e8df218a7a6f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homodolicholide 10V, Negative-QTOFsplash10-0006-0001900000-8af49296a318cd1d717b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homodolicholide 20V, Negative-QTOFsplash10-01po-9405400000-5e353019918c2ff4bebd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homodolicholide 40V, Negative-QTOFsplash10-052n-1005900000-78954c278fc399792a232021-09-23Wishart 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 IDFDB012103
KNApSAcK IDC00013480
Chemspider ID35013676
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15340661
PDB IDNot Available
ChEBI ID168025
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.