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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:56 UTC
Update Date2022-03-07 02:52:11 UTC
HMDB IDHMDB0029525
Secondary Accession Numbers
  • HMDB29525
Metabolite Identification
Common Name7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone
Description7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone, also known as tylophorin or 2,3,6,7-tetramethoxyphenanthro(9,10:6,7')indolizidine, belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. Based on a literature review very few articles have been published on 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone.
Structure
Data?1582753431
Synonyms
ValueSource
(+)-TylophorineHMDB
2,3,6,7-Tetramethoxyphenanthro(9,10:6,7')indolizidineHMDB
2,3,6,7-Tetramethoxyphenanthro[9,10:6',7']indolizidineHMDB
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone, 9ciHMDB
TylophorinHMDB
TylophorineHMDB
Tylophorine (8ci)HMDB
Chemical FormulaC21H26O4
Average Molecular Weight342.4287
Monoisotopic Molecular Weight342.18310932
IUPAC Name7-(4-hydroxy-3-methoxyphenyl)-5-methoxy-1-phenylheptan-3-one
Traditional Name7-(4-hydroxy-3-methoxyphenyl)-5-methoxy-1-phenylheptan-3-one
CAS Registry Number83161-95-9
SMILES
COC(CCC1=CC(OC)=C(O)C=C1)CC(=O)CCC1=CC=CC=C1
InChI Identifier
InChI=1S/C21H26O4/c1-24-19(12-9-17-10-13-20(23)21(14-17)25-2)15-18(22)11-8-16-6-4-3-5-7-16/h3-7,10,13-14,19,23H,8-9,11-12,15H2,1-2H3
InChI KeyXYIISUAVSYEQLI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassLinear diarylheptanoids
Direct ParentLinear diarylheptanoids
Alternative Parents
Substituents
  • Linear 1,7-diphenylheptane skeleton
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ketone
  • Dialkyl ether
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.25 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0051 g/LALOGPS
logP4.11ALOGPS
logP4.5ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)10.28ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity98.75 m³·mol⁻¹ChemAxon
Polarizability38.52 ųChemAxon
Number of Rings2ChemAxon
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]+184.33631661259
DarkChem[M-H]-181.23231661259
DeepCCS[M+H]+183.61430932474
DeepCCS[M-H]-181.25630932474
DeepCCS[M-2H]-215.13630932474
DeepCCS[M+Na]+190.49430932474
AllCCS[M+H]+187.932859911
AllCCS[M+H-H2O]+184.632859911
AllCCS[M+NH4]+190.932859911
AllCCS[M+Na]+191.832859911
AllCCS[M-H]-188.432859911
AllCCS[M+Na-2H]-189.032859911
AllCCS[M+HCOO]-189.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanoneCOC(CCC1=CC(OC)=C(O)C=C1)CC(=O)CCC1=CC=CC=C13937.0Standard polar33892256
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanoneCOC(CCC1=CC(OC)=C(O)C=C1)CC(=O)CCC1=CC=CC=C12588.4Standard non polar33892256
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanoneCOC(CCC1=CC(OC)=C(O)C=C1)CC(=O)CCC1=CC=CC=C12773.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone,1TMS,isomer #1COC1=CC(CCC(CC(=O)CCC2=CC=CC=C2)OC)=CC=C1O[Si](C)(C)C2800.8Semi standard non polar33892256
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone,1TMS,isomer #2COC1=CC(CCC(CC(=CCC2=CC=CC=C2)O[Si](C)(C)C)OC)=CC=C1O2865.4Semi standard non polar33892256
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone,1TMS,isomer #3COC1=CC(CCC(C=C(CCC2=CC=CC=C2)O[Si](C)(C)C)OC)=CC=C1O2837.2Semi standard non polar33892256
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone,2TMS,isomer #1COC1=CC(CCC(CC(=CCC2=CC=CC=C2)O[Si](C)(C)C)OC)=CC=C1O[Si](C)(C)C2914.7Semi standard non polar33892256
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone,2TMS,isomer #1COC1=CC(CCC(CC(=CCC2=CC=CC=C2)O[Si](C)(C)C)OC)=CC=C1O[Si](C)(C)C2652.1Standard non polar33892256
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone,2TMS,isomer #2COC1=CC(CCC(C=C(CCC2=CC=CC=C2)O[Si](C)(C)C)OC)=CC=C1O[Si](C)(C)C2872.9Semi standard non polar33892256
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone,2TMS,isomer #2COC1=CC(CCC(C=C(CCC2=CC=CC=C2)O[Si](C)(C)C)OC)=CC=C1O[Si](C)(C)C2592.5Standard non polar33892256
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone,1TBDMS,isomer #1COC1=CC(CCC(CC(=O)CCC2=CC=CC=C2)OC)=CC=C1O[Si](C)(C)C(C)(C)C3038.7Semi standard non polar33892256
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone,1TBDMS,isomer #2COC1=CC(CCC(CC(=CCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)OC)=CC=C1O3123.3Semi standard non polar33892256
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone,1TBDMS,isomer #3COC1=CC(CCC(C=C(CCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)OC)=CC=C1O3090.0Semi standard non polar33892256
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone,2TBDMS,isomer #1COC1=CC(CCC(CC(=CCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)OC)=CC=C1O[Si](C)(C)C(C)(C)C3360.9Semi standard non polar33892256
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone,2TBDMS,isomer #1COC1=CC(CCC(CC(=CCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)OC)=CC=C1O[Si](C)(C)C(C)(C)C3071.4Standard non polar33892256
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone,2TBDMS,isomer #2COC1=CC(CCC(C=C(CCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)OC)=CC=C1O[Si](C)(C)C(C)(C)C3324.0Semi standard non polar33892256
7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone,2TBDMS,isomer #2COC1=CC(CCC(C=C(CCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)OC)=CC=C1O[Si](C)(C)C(C)(C)C2992.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5i-1920000000-df09303d9e2186d5e1ad2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone GC-MS (1 TMS) - 70eV, Positivesplash10-009m-9837000000-6cf1fd5d3db0686a68b12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone 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 - 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone 10V, Positive-QTOFsplash10-0006-0319000000-e16fae94d47076b02d622015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone 20V, Positive-QTOFsplash10-001l-1922000000-2146ca40a9d2ce4ec35e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone 40V, Positive-QTOFsplash10-0bu9-3900000000-51b231f318e5e9bc79912015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone 10V, Negative-QTOFsplash10-0006-0119000000-2bdbdf7919ff5dc720152015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone 20V, Negative-QTOFsplash10-0007-1946000000-38abe83a339e5f88c1c62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone 40V, Negative-QTOFsplash10-0002-3940000000-88da8ecbfd89e52d3e8b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone 10V, Positive-QTOFsplash10-0006-1398000000-b36436d603e8d8a0cde32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone 20V, Positive-QTOFsplash10-0a4l-3962000000-c1f752461564f3154b332021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone 40V, Positive-QTOFsplash10-0a6u-3920000000-28921a584e30f4b5ce5f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone 10V, Negative-QTOFsplash10-0006-0109000000-c5f40e2f82b81a1639712021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone 20V, Negative-QTOFsplash10-0abd-0947000000-2a795246211015568c8e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-(4-Hydroxy-3-methoxyphenyl)-5-methoxy-1-phenyl-3-heptanone 40V, Negative-QTOFsplash10-0fgd-3971000000-b5b695a50cb40b355f0f2021-09-25Wishart 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 IDFDB000665
KNApSAcK IDNot Available
Chemspider ID4477747
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5319454
PDB IDNot Available
ChEBI ID66032
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1810191
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lee YZ, Huang CW, Yang CW, Hsu HY, Kang IJ, Chao YS, Chen IS, Chang HY, Lee SJ: Isolation and biological activities of phenanthroindolizidine and septicine alkaloids from the Formosan Tylophora ovata. Planta Med. 2011 Nov;77(17):1932-8. doi: 10.1055/s-0030-1271199. Epub 2011 Jul 4. [PubMed:21728149 ]
  2. Stoye A, Opatz T: Racemization-free synthesis of (S)-(+)-tylophorine from L-proline by radical cyclization. Org Lett. 2010 May 7;12(9):2140-1. doi: 10.1021/ol100652b. [PubMed:20377275 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .