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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:16 UTC
Update Date2022-03-07 02:52:27 UTC
HMDB IDHMDB0030174
Secondary Accession Numbers
  • HMDB30174
Metabolite Identification
Common NameIsotetrandrine
DescriptionIsotetrandrine, also known as isosinomenine a or NSC 97338, belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. Isotetrandrine is a very strong basic compound (based on its pKa). Outside of the human body, isotetrandrine has been detected, but not quantified in, herbs and spices. This could make isotetrandrine a potential biomarker for the consumption of these foods.
Structure
Data?1563861948
Synonyms
ValueSource
(+)-IsotetrandrineHMDB
1-IsotetrandrineHMDB
6,6',7,12-Tetramethoxy-2,2'-dimethyl-berbamanHMDB
Isosinomenine aHMDB
NSC 97338HMDB
O,O'-dimethylobamegineHMDB
O,O'-dimethylstepholineHMDB
O,O-DimethylobamegineHMDB
O,O-DimethylstepholineHMDB
O-MethylberbamineHMDB
6,6',7,12-Tetramethoxy-2,2'-dimethyl-1 beta-berbamanMeSH
D-TetrandrineMeSH
HanjisongMeSH
Isotetrandrine dihydrochlorideMeSH
TetradrineMeSH
Tetrandrine, (1'beta)-isomerMeSH
TetrandrineMeSH
Tetrandrine dihydrochloride, (1beta)-isomerMeSH
Chemical FormulaC38H42N2O6
Average Molecular Weight622.7499
Monoisotopic Molecular Weight622.304287086
IUPAC Name9,20,21,25-tetramethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24(32),25,27(31),35-dodecaene
Traditional Name9,20,21,25-tetramethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24(32),25,27(31),35-dodecaene
CAS Registry Number477-57-6
SMILES
COC1=CC=C2CC3N(C)CCC4=C3C(OC3=CC5=C(CCN(C)C5CC5=CC=C(OC1=C2)C=C5)C=C3OC)=C(OC)C(OC)=C4
InChI Identifier
InChI=1S/C38H42N2O6/c1-39-15-13-25-20-32(42-4)34-22-28(25)29(39)17-23-7-10-27(11-8-23)45-33-19-24(9-12-31(33)41-3)18-30-36-26(14-16-40(30)2)21-35(43-5)37(44-6)38(36)46-34/h7-12,19-22,29-30H,13-18H2,1-6H3
InChI KeyWVTKBKWTSCPRNU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassNot Available
Sub ClassNot Available
Direct ParentLignans, neolignans and related compounds
Alternative Parents
Substituents
  • Oxyneolignan skeleton
  • Diaryl ether
  • Tetrahydroisoquinoline
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point182 - 183 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.003 g/LALOGPS
logP5.55ALOGPS
logP6.48ChemAxon
logS-5.3ALOGPS
pKa (Strongest Basic)8.52ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area61.86 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity180.11 m³·mol⁻¹ChemAxon
Polarizability68.63 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+239.27131661259
DarkChem[M-H]-232.57531661259
DeepCCS[M+H]+256.15130932474
DeepCCS[M-H]-254.11230932474
DeepCCS[M-2H]-287.35330932474
DeepCCS[M+Na]+262.65530932474
AllCCS[M+H]+246.632859911
AllCCS[M+H-H2O]+245.332859911
AllCCS[M+NH4]+247.732859911
AllCCS[M+Na]+248.032859911
AllCCS[M-H]-241.232859911
AllCCS[M+Na-2H]-243.032859911
AllCCS[M+HCOO]-245.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsotetrandrineCOC1=CC=C2CC3N(C)CCC4=C3C(OC3=CC5=C(CCN(C)C5CC5=CC=C(OC1=C2)C=C5)C=C3OC)=C(OC)C(OC)=C45711.3Standard polar33892256
IsotetrandrineCOC1=CC=C2CC3N(C)CCC4=C3C(OC3=CC5=C(CCN(C)C5CC5=CC=C(OC1=C2)C=C5)C=C3OC)=C(OC)C(OC)=C44714.0Standard non polar33892256
IsotetrandrineCOC1=CC=C2CC3N(C)CCC4=C3C(OC3=CC5=C(CCN(C)C5CC5=CC=C(OC1=C2)C=C5)C=C3OC)=C(OC)C(OC)=C44537.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isotetrandrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-0000094000-16e7e9ec7c849aa8fbde2017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Isotetrandrine 6V, Positive-QTOFsplash10-00di-0000009000-544f8625c973d44a95172021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isotetrandrine 6V, Positive-QTOFsplash10-00di-0000009000-7cd87556e84cce5732312021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isotetrandrine 10V, Positive-QTOFsplash10-00di-0000039000-76a7f64bf880d385153d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isotetrandrine 20V, Positive-QTOFsplash10-006x-0000093000-34a3976b989b8ead22062016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isotetrandrine 40V, Positive-QTOFsplash10-03gi-0000090000-fa6d47c3b396f51902412016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isotetrandrine 10V, Negative-QTOFsplash10-00di-0000009000-f6f0adfcee090fea8e0a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isotetrandrine 20V, Negative-QTOFsplash10-05fr-0000049000-5571f5eae59c0fe4abd02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isotetrandrine 40V, Negative-QTOFsplash10-00os-0000090000-c489b8ee8fa69f3ed5f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isotetrandrine 10V, Positive-QTOFsplash10-00di-0000009000-2e1e1758bf77504b12f82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isotetrandrine 20V, Positive-QTOFsplash10-00dl-0000089000-896c1e5c16b5e3465ae52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isotetrandrine 40V, Positive-QTOFsplash10-00al-1000091000-6979ac568989952592b82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isotetrandrine 10V, Negative-QTOFsplash10-00di-0000009000-4e8191be91182248f3a22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isotetrandrine 20V, Negative-QTOFsplash10-00dr-0000089000-b77b4f80f79c3c02f2922021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isotetrandrine 40V, Negative-QTOFsplash10-00pi-0000091000-62acbe5b9bef88e457172021-09-24Wishart 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 IDFDB001990
KNApSAcK IDC00025313
Chemspider ID5229
KEGG Compound IDC17060
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5422
PDB IDNot Available
ChEBI ID397244
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .