ContaminantDB: Bakkenolide D

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

Record Information

Version

1.0

Creation Date

2016-05-26 00:49:02 UTC

Update Date

2016-11-09 01:18:47 UTC

Accession Number

CHEM028944

Identification

Common Name

Bakkenolide D

Class

Small Molecule

Description

Bakkenolide D is found in giant butterbur. Bakkenolide D 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
S-Fukinolide	HMDB
3-(Acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl (2E)-3-(methylsulfanyl)prop-2-enoic acid	Generator
3-(Acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl (2E)-3-(methylsulphanyl)prop-2-enoate	Generator
3-(Acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl (2E)-3-(methylsulphanyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₁H₂₈O₆S

Average Molecular Mass

408.508 g/mol

Monoisotopic Mass

408.161 g/mol

CAS Registry Number

18456-03-6

IUPAC Name

3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl (2E)-3-(methylsulfanyl)prop-2-enoate

Traditional Name

3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-4-yl (2E)-3-(methylsulfanyl)prop-2-enoate

SMILES

CS\C=C\C(=O)OC1CCC(C)C2(C)CC3(C(OC(C)=O)C12)C(=C)COC3=O

InChI Identifier

InChI=1S/C21H28O6S/c1-12-6-7-15(27-16(23)8-9-28-5)17-18(26-14(3)22)21(11-20(12,17)4)13(2)10-25-19(21)24/h8-9,12,15,17-18H,2,6-7,10-11H2,1,3-5H3/b9-8+

InChI Key

LWHLMCCRIWZBQO-CMDGGOBGSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Tricarboxylic acid or derivatives
Gamma butyrolactone
Vinylogous thioester
Acrylic acid or derivatives
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Thioenolether
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Sulfenyl compound
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	0.0024 g/L	ALOGPS
logP	3.15	ALOGPS
logP	2.96	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	105.29 m³·mol⁻¹	ChemAxon
Polarizability	42.38 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-2096000000-127a97a26a37fa000630	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	splash10-0pbc-1339400000-0aca307ad51758c001f0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udm-3987000000-be55624df7db07ed1f47	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9550000000-0622b67bb3bf0d2e4b47	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4j-8019500000-0cee82757e3ff155dfc7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9013000000-dc3736b2cbfaed31a02e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9041000000-5c074c776272a17d1d52	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000400000-75a5d8f8bd30a0b93a5e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000100000-f3dd72dbe8d14845d991	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052g-9000000000-34082956b045ac84e6be	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0026900000-3b1f7c7b9f39147cd7ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052p-0092100000-71b2e7543ee2af54d94a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03fs-6891000000-114aad8126c9fb1345c5	Spectrum