ContaminantDB: Petasitin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 01:13:48 UTC

Update Date

2016-11-09 01:18:54 UTC

Accession Number

CHEM029537

Identification

Common Name

Petasitin

Class

Small Molecule

Description

Petasitin is found in giant butterbur. Petasitin is a constituent of Petasites japonicus (sweet coltsfoot)

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
7-(2-Hydroxypropan-2-yl)-1,8a-dimethyl-6-oxo-1,2,3,4,6,8a-hexahydronaphthalen-2-yl (2E)-2-methylbut-2-enoic acid	HMDB

Chemical Formula

C₂₀H₂₈O₄

Average Molecular Mass

332.434 g/mol

Monoisotopic Mass

332.199 g/mol

CAS Registry Number

19887-90-2

IUPAC Name

7-(2-hydroxypropan-2-yl)-1,8a-dimethyl-6-oxo-1,2,3,4,6,8a-hexahydronaphthalen-2-yl (2E)-2-methylbut-2-enoate

Traditional Name

7-(2-hydroxypropan-2-yl)-1,8a-dimethyl-6-oxo-1,2,3,4-tetrahydronaphthalen-2-yl (2E)-2-methylbut-2-enoate

SMILES

C\C=C(/C)C(=O)OC1CCC2=CC(=O)C(=CC2(C)C1C)C(C)(C)O

InChI Identifier

InChI=1S/C20H28O4/c1-7-12(2)18(22)24-17-9-8-14-10-16(21)15(19(4,5)23)11-20(14,6)13(17)3/h7,10-11,13,17,23H,8-9H2,1-6H3/b12-7+

InChI Key

ITHGBLBTVGSKLJ-KPKJPENVSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Fatty acid ester
Fatty acyl
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	3.6	ALOGPS
logP	3.74	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	14.52	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	96.3 m³·mol⁻¹	ChemAxon
Polarizability	37.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0536-7944000000-2a155bcef2145a436dd4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-053i-9064000000-507f55b081d186bd0552	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-2049000000-5882858a1005a4df6bce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9282000000-eabbbecfe23d836066f9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zgi-9220000000-0bee1985f7fe2d65685c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1029000000-cbb56a2173c042197650	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-008a-7298000000-7b1169506b9cdeb2bfe8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0535-9670000000-ff59e995c757e71d8fb1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0090000000-2efbb229ce06583ab870	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0090000000-a4ee3cfe858c27569e47	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0c29-6970000000-a10a44debef498846c8c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001j-6019000000-21d17dd462966b91c6c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001j-9083000000-f43ebe52aafa312e9bc8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-9000000000-57bfae6a6fc4e1faa376	Spectrum