Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:24:16 UTC
Update Date2022-03-07 02:54:51 UTC
HMDB IDHMDB0036284
Secondary Accession Numbers
  • HMDB36284
Metabolite Identification
Common NameCampesteryl caffeate
DescriptionCampesteryl caffeate belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group. Campesteryl caffeate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862850
Synonyms
ValueSource
Campesteryl caffeic acidGenerator
14-(5,6-Dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acidGenerator
Chemical FormulaC37H54O4
Average Molecular Weight562.8223
Monoisotopic Molecular Weight562.402210216
IUPAC Name14-(5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Traditional Name14-(5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate
CAS Registry Number75873-74-4
SMILES
CC(C)C(C)CCC(C)C1CCC2C3CC=C4CC(CCC4(C)C3CCC12C)OC(=O)\C=C/C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C37H54O4/c1-23(2)24(3)7-8-25(4)30-13-14-31-29-12-11-27-22-28(17-19-36(27,5)32(29)18-20-37(30,31)6)41-35(40)16-10-26-9-15-33(38)34(39)21-26/h9-11,15-16,21,23-25,28-32,38-39H,7-8,12-14,17-20,22H2,1-6H3/b16-10-
InChI KeyZXDDRZYEBDQKAY-YBEGLDIGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homopolycyclic 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.8e-05 g/LALOGPS
logP7.93ALOGPS
logP9.83ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity168.69 m³·mol⁻¹ChemAxon
Polarizability66.84 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-263.84430932474
DeepCCS[M+Na]+240.20730932474
AllCCS[M+H]+244.132859911
AllCCS[M+H-H2O]+243.032859911
AllCCS[M+NH4]+245.132859911
AllCCS[M+Na]+245.432859911
AllCCS[M-H]-226.332859911
AllCCS[M+Na-2H]-229.832859911
AllCCS[M+HCOO]-233.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Campesteryl caffeateCC(C)C(C)CCC(C)C1CCC2C3CC=C4CC(CCC4(C)C3CCC12C)OC(=O)\C=C/C1=CC(O)=C(O)C=C14672.2Standard polar33892256
Campesteryl caffeateCC(C)C(C)CCC(C)C1CCC2C3CC=C4CC(CCC4(C)C3CCC12C)OC(=O)\C=C/C1=CC(O)=C(O)C=C14262.0Standard non polar33892256
Campesteryl caffeateCC(C)C(C)CCC(C)C1CCC2C3CC=C4CC(CCC4(C)C3CCC12C)OC(=O)\C=C/C1=CC(O)=C(O)C=C14718.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Campesteryl caffeate,1TMS,isomer #1CC(C)C(C)CCC(C)C1CCC2C3CC=C4CC(OC(=O)/C=C\C5=CC=C(O)C(O[Si](C)(C)C)=C5)CCC4(C)C3CCC12C4689.5Semi standard non polar33892256
Campesteryl caffeate,1TMS,isomer #2CC(C)C(C)CCC(C)C1CCC2C3CC=C4CC(OC(=O)/C=C\C5=CC=C(O[Si](C)(C)C)C(O)=C5)CCC4(C)C3CCC12C4699.0Semi standard non polar33892256
Campesteryl caffeate,2TMS,isomer #1CC(C)C(C)CCC(C)C1CCC2C3CC=C4CC(OC(=O)/C=C\C5=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C5)CCC4(C)C3CCC12C4691.5Semi standard non polar33892256
Campesteryl caffeate,1TBDMS,isomer #1CC(C)C(C)CCC(C)C1CCC2C3CC=C4CC(OC(=O)/C=C\C5=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C5)CCC4(C)C3CCC12C4922.4Semi standard non polar33892256
Campesteryl caffeate,1TBDMS,isomer #2CC(C)C(C)CCC(C)C1CCC2C3CC=C4CC(OC(=O)/C=C\C5=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C5)CCC4(C)C3CCC12C4923.2Semi standard non polar33892256
Campesteryl caffeate,2TBDMS,isomer #1CC(C)C(C)CCC(C)C1CCC2C3CC=C4CC(OC(=O)/C=C\C5=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C5)CCC4(C)C3CCC12C5124.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Campesteryl caffeate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0015-3319170000-2945d1f575f4e706ca262017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Campesteryl caffeate GC-MS (1 TMS) - 70eV, Positivesplash10-0aou-4029027000-a9fa95a80c03c8e482432017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Campesteryl caffeate GC-MS ("Campesteryl caffeate,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Campesteryl caffeate GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Campesteryl caffeate GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Campesteryl caffeate GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Campesteryl caffeate GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Campesteryl caffeate GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campesteryl caffeate 10V, Positive-QTOFsplash10-03di-1603490000-640f12246e357116ab052016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campesteryl caffeate 20V, Positive-QTOFsplash10-03dr-4917410000-ce3f105f4a60d3a181972016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campesteryl caffeate 40V, Positive-QTOFsplash10-05n0-5329000000-c1e54ee6dd46380d3df52016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campesteryl caffeate 10V, Negative-QTOFsplash10-03di-0204090000-2be3d71fc190c2755e672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campesteryl caffeate 20V, Negative-QTOFsplash10-01ot-0709130000-12e1253744e19dd0a07b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campesteryl caffeate 40V, Negative-QTOFsplash10-01qa-2409000000-65a053075c70bcd3f8222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campesteryl caffeate 10V, Positive-QTOFsplash10-03di-0112590000-82803eec9ff7df60736e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campesteryl caffeate 20V, Positive-QTOFsplash10-08fr-3142390000-e8eb2c30f65929c4cd122021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campesteryl caffeate 40V, Positive-QTOFsplash10-08gu-4921100000-900ccd0e20accfd9c69f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campesteryl caffeate 10V, Negative-QTOFsplash10-03di-0000090000-b61d1d88f65f652860912021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campesteryl caffeate 20V, Negative-QTOFsplash10-03di-0903080000-173814564b3f5fc2eb152021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campesteryl caffeate 40V, Negative-QTOFsplash10-0019-1900110000-8854af825b61a58e3df72021-09-25Wishart 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 IDFDB015150
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751941
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.