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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:44:11 UTC
Update Date2022-03-07 03:18:14 UTC
HMDB IDHMDB0240249
Secondary Accession NumbersNone
Metabolite Identification
Common NameTritoqualine
DescriptionTritoqualine, also known as hypostamine or inhibostamin, belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide. In humans, tritoqualine is involved in the tritoqualine h1-antihistamine action pathway. Tritoqualine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Tritoqualine.
Structure
Data?1563892736
Synonyms
ValueSource
HypostamineKegg
35NZHMDB
554lHMDB
HypostaminHMDB
InhibostaminHMDB
L 554HMDB
LivalfaHMDB
TritocalineHMDB
4,5,6-Triethoxy-7-amino-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)phthalideHMDB
Chiesi brand OF tritoqualineHMDB
TritoqualinHMDB
TritoqualineHMDB
Chemical FormulaC26H32N2O8
Average Molecular Weight500.548
Monoisotopic Molecular Weight500.215865998
IUPAC Name7-amino-4,5,6-triethoxy-3-{4-methoxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-1,3-dihydro-2-benzofuran-1-one
Traditional Nametritoqualine
CAS Registry Number14504-73-5
SMILES
CCOC1=C(OCC)C(OCC)=C(N)C2=C1C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(OC)=C12
InChI Identifier
InChI=1S/C26H32N2O8/c1-6-31-23-17-16(18(27)24(32-7-2)25(23)33-8-3)26(29)36-21(17)19-15-13(9-10-28(19)4)11-14-20(22(15)30-5)35-12-34-14/h11,19,21H,6-10,12,27H2,1-5H3
InChI KeyIRGJVQIJENCTQF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassPhthalide isoquinolines
Sub ClassNot Available
Direct ParentPhthalide isoquinolines
Alternative Parents
Substituents
  • Phthalide isoquinoline
  • Gallic acid or derivatives
  • Benzofuranone
  • Isobenzofuranone
  • Phthalide
  • Tetrahydroisoquinoline
  • Benzodioxole
  • Isocoumaran
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • Vinylogous amide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • Lactone
  • Carboxylic acid ester
  • Azacycle
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Primary amine
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process

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
logP2.65ALOGPS
logP3.31ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)13.29ChemAxon
pKa (Strongest Basic)7.06ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area110.94 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity132.49 m³·mol⁻¹ChemAxon
Polarizability52.8 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M-H]-220.331661259
AllCCS[M+H]+216.86531661259
DeepCCS[M-2H]-241.69730932474
DeepCCS[M+Na]+217.12230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TritoqualineCCOC1=C(OCC)C(OCC)=C(N)C2=C1C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(OC)=C124880.8Standard polar33892256
TritoqualineCCOC1=C(OCC)C(OCC)=C(N)C2=C1C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(OC)=C123816.8Standard non polar33892256
TritoqualineCCOC1=C(OCC)C(OCC)=C(N)C2=C1C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(OC)=C123602.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tritoqualine,1TMS,isomer #1CCOC1=C(N[Si](C)(C)C)C2=C(C(OCC)=C1OCC)C(C1C3=C(OC)C4=C(C=C3CCN1C)OCO4)OC2=O3715.4Semi standard non polar33892256
Tritoqualine,1TMS,isomer #1CCOC1=C(N[Si](C)(C)C)C2=C(C(OCC)=C1OCC)C(C1C3=C(OC)C4=C(C=C3CCN1C)OCO4)OC2=O3481.3Standard non polar33892256
Tritoqualine,1TMS,isomer #1CCOC1=C(N[Si](C)(C)C)C2=C(C(OCC)=C1OCC)C(C1C3=C(OC)C4=C(C=C3CCN1C)OCO4)OC2=O5067.9Standard polar33892256
Tritoqualine,2TMS,isomer #1CCOC1=C(OCC)C2=C(C(=O)OC2C2C3=C(OC)C4=C(C=C3CCN2C)OCO4)C(N([Si](C)(C)C)[Si](C)(C)C)=C1OCC3735.7Semi standard non polar33892256
Tritoqualine,2TMS,isomer #1CCOC1=C(OCC)C2=C(C(=O)OC2C2C3=C(OC)C4=C(C=C3CCN2C)OCO4)C(N([Si](C)(C)C)[Si](C)(C)C)=C1OCC3615.2Standard non polar33892256
Tritoqualine,2TMS,isomer #1CCOC1=C(OCC)C2=C(C(=O)OC2C2C3=C(OC)C4=C(C=C3CCN2C)OCO4)C(N([Si](C)(C)C)[Si](C)(C)C)=C1OCC4750.1Standard polar33892256
Tritoqualine,1TBDMS,isomer #1CCOC1=C(N[Si](C)(C)C(C)(C)C)C2=C(C(OCC)=C1OCC)C(C1C3=C(OC)C4=C(C=C3CCN1C)OCO4)OC2=O3870.7Semi standard non polar33892256
Tritoqualine,1TBDMS,isomer #1CCOC1=C(N[Si](C)(C)C(C)(C)C)C2=C(C(OCC)=C1OCC)C(C1C3=C(OC)C4=C(C=C3CCN1C)OCO4)OC2=O3659.5Standard non polar33892256
Tritoqualine,1TBDMS,isomer #1CCOC1=C(N[Si](C)(C)C(C)(C)C)C2=C(C(OCC)=C1OCC)C(C1C3=C(OC)C4=C(C=C3CCN1C)OCO4)OC2=O5107.4Standard polar33892256
Tritoqualine,2TBDMS,isomer #1CCOC1=C(OCC)C2=C(C(=O)OC2C2C3=C(OC)C4=C(C=C3CCN2C)OCO4)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1OCC3994.5Semi standard non polar33892256
Tritoqualine,2TBDMS,isomer #1CCOC1=C(OCC)C2=C(C(=O)OC2C2C3=C(OC)C4=C(C=C3CCN2C)OCO4)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1OCC3963.2Standard non polar33892256
Tritoqualine,2TBDMS,isomer #1CCOC1=C(OCC)C2=C(C(=O)OC2C2C3=C(OC)C4=C(C=C3CCN2C)OCO4)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1OCC4833.8Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tritoqualine 10V, Positive-QTOFsplash10-0udi-0000970000-2073e34843dbe1f78ccf2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tritoqualine 20V, Positive-QTOFsplash10-0kn9-0170910000-e6c4f40e34955b456ff92017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tritoqualine 40V, Positive-QTOFsplash10-0f80-0090000000-7cc49a686e10da15139a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tritoqualine 10V, Negative-QTOFsplash10-0002-0000900000-290845d9729e8a80a7ce2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tritoqualine 20V, Negative-QTOFsplash10-056r-0010900000-8c440296c4d90628f8542017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tritoqualine 40V, Negative-QTOFsplash10-0007-5309800000-acf5193382ea7b5f682b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tritoqualine 10V, Negative-QTOFsplash10-0002-0000900000-4d069a52fe971059afe42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tritoqualine 20V, Negative-QTOFsplash10-0002-0000900000-fadeb483bbec9fb9d0ba2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tritoqualine 40V, Negative-QTOFsplash10-0a6u-0000900000-d7bc9e993995d947cd0e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tritoqualine 10V, Positive-QTOFsplash10-0udi-0000090000-b9e3b6ce832a852588dc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tritoqualine 20V, Positive-QTOFsplash10-0udi-0010290000-16dc28435713e30f6b642021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tritoqualine 40V, Positive-QTOFsplash10-00dl-0270900000-acd5df7fb82c342946002021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDDB13711
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID65119
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTritoqualine
METLIN IDNot Available
PubChem Compound72145
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. Umezu K, Yuasa S, Ichikawa A: Inhibitory mechanism of tritoqualine on histamine release from mast cells. Biochem Pharmacol. 1986 Sep 15;35(18):3137-42. [PubMed:2428378 ]