Record Information
Version1.0
Creation date2010-04-08 22:06:54 UTC
Update date2018-05-29 00:40:40 UTC
Primary IDFDB005931
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePretazettine
DescriptionPretazettine, also known as pretazettine hydrochloride, (6abeta,8beta)-isomer, is a member of the class of compounds known as tazettine-type amaryllidaceae alkaloids. Tazettine-type amaryllidaceae alkaloids are amaryllidaceae alkaloids derived from the haemanthamine-type alkaloids, which are characterized as a linkage between C6 and C11 by an oxygen atom to form a [3,4-g]benzopyran framework. Pretazettine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Pretazettine can be found in lovage, which makes pretazettine a potential biomarker for the consumption of this food product.
CAS Number17322-84-8
Structure
Thumb
Synonyms
SynonymSource
Pretazettinebiospider
Pretazzetine hydrochloridebiospider
Tazettine, 6a-deoxy-8-hydroxy-, (6abeta,8beta)-biospider
Predicted Properties
PropertyValueSource
Water Solubility2.46 g/LALOGPS
logP0.73ALOGPS
logP1.1ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)11.54ChemAxon
pKa (Strongest Basic)7.71ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.39 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.89 m³·mol⁻¹ChemAxon
Polarizability34.52 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H21NO5
IUPAC name(1S,11R,13R,16S,18S)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-11-ol
InChI IdentifierInChI=1S/C18H21NO5/c1-19-8-16-18(4-3-10(21-2)5-15(18)19)12-7-14-13(22-9-23-14)6-11(12)17(20)24-16/h3-4,6-7,10,15-17,20H,5,8-9H2,1-2H3/t10-,15+,16+,17-,18+/m1/s1
InChI KeyKLJOYDMUWKSYBP-YNBLHMCPSA-N
Isomeric SMILESCO[C@H]1C[C@@H]2N(C)C[C@@H]3O[C@@H](O)C4=CC5=C(OCO5)C=C4[C@@]23C=C1
Average Molecular Weight331.363
Monoisotopic Molecular Weight331.141972787
Classification
Description belongs to the class of organic compounds known as tazettine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids derived from the haemanthamine-type alkaloids, which are characterized as a linkage between C6 and C11 by an oxygen atom to form a [3,4-g]benzopyran framework.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAmaryllidaceae alkaloids
Sub ClassTazettine-type amaryllidaceae alkaloids
Direct ParentTazettine-type amaryllidaceae alkaloids
Alternative Parents
Substituents
  • Tazettine alkaloid skeleton
  • Benzopyran
  • Isochromane
  • 2-benzopyran
  • Benzodioxole
  • Indole or derivatives
  • Aralkylamine
  • N-alkylpyrrolidine
  • Benzenoid
  • Pyrrolidine
  • Hemiacetal
  • Tertiary amine
  • Tertiary aliphatic amine
  • Oxacycle
  • Acetal
  • Ether
  • Dialkyl ether
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-e2435e272ca9f1a2d42fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0059000000-cafe65902dcbae1ebf7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054o-1490000000-3350b494f2ef37f52c8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0119000000-8e3643f4ca920a1640feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0059000000-11edba5eac58052a23abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03ds-2931000000-9cde7fc633100e58bb8cView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08536
Pubchem Compound ID73360
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDPRETAZETTINE
BIGG IDNot Available
KNApSAcK IDC00001580
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti proteinigenicDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
HIV-reverse-transcriptase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).