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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:07 UTC
Update Date2019-01-11 19:40:04 UTC
HMDB IDHMDB0030323
Secondary Accession Numbers
  • HMDB30323
Metabolite Identification
Common NamePaxilline
DescriptionTremorgenic agent from Penicillium paxilli, Acremonium lorii, Emericella foveolata, Emericella desertorum and Emericella striata Paxilline is a potassium channel blocker. Paxilline is a toxic, tremorgenic indole alkaloid produced by Penicillium paxilli
Structure
Data?1547235604
SynonymsNot Available
Chemical FormulaC27H33NO4
Average Molecular Weight435.5552
Monoisotopic Molecular Weight435.240958549
IUPAC Name(1S,2R,5S,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one
Traditional Namepaxilline
CAS Registry Number57186-25-1
SMILES
[H][C@]12CC3=C(NC4=CC=CC=C34)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H](C(=O)C=C3[C@]1(O)CC2)C(C)(C)O
InChI Identifier
InChI=1S/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3/t15-,21-,23-,25+,26+,27+/m0/s1
InChI KeyACNHBCIZLNNLRS-UBGQALKQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as naphthopyrans. These are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNot Available
Direct ParentNaphthopyrans
Alternative Parents
Substituents
  • Naphthopyran
  • Naphthalene
  • Indole or derivatives
  • Indole
  • Dihydropyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Tertiary alcohol
  • Pyrrole
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Azacycle
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point252 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0014 g/LALOGPS
logP4.38ALOGPS
logP3.62ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)13.56ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity123.22 m³·mol⁻¹ChemAxon
Polarizability50.07 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9645500000-b712ecd3bb25e698284eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0m90-9011570000-915adc6c191ba0623cd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0001900000-8605cb3753956fb199daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0202900000-50009a61ed6eb59db7beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-7609100000-5673b5a2dfedddad8880View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1000900000-9d1902d4d59212d80917View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-3003900000-65a27849e60aa5a8e142View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-2219000000-c067ab4edf80e9e85544View in MoNA
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
FoodDB IDFDB002165
KNApSAcK IDC00023582
Chemspider ID4535
KEGG Compound IDC13782
BioCyc IDCPD-16744
BiGG IDNot Available
Wikipedia LinkPaxilline
METLIN IDNot Available
PubChem Compound105008
PDB IDNot Available
ChEBI 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.. .