ContaminantDB: Crispolide

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

Record Information

Version

1.0

Creation Date

2016-05-26 01:50:33 UTC

Update Date

2016-11-09 01:19:03 UTC

Accession Number

CHEM030357

Identification

Common Name

Crispolide

Class

Small Molecule

Description

Crispolide is found in herbs and spices. Crispolide is a constituent of Tanacetum vulgare var. crispum.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1b-Hydroperoxy-5b-hydroxy-4,14-cyclo-9,11-germacradien-12,6a-olide	HMDB

Chemical Formula

C₁₅H₂₀O₅

Average Molecular Mass

280.316 g/mol

Monoisotopic Mass

280.131 g/mol

CAS Registry Number

83217-86-1

IUPAC Name

(2S,3S,7S,11R)-11-hydroperoxy-2-hydroxy-1-methyl-6-methylidene-4-oxatricyclo[8.3.1.0^{3,7}]tetradec-9-en-5-one

Traditional Name

(2S,3S,7S,11R)-11-hydroperoxy-2-hydroxy-1-methyl-6-methylidene-4-oxatricyclo[8.3.1.0^{3,7}]tetradec-9-en-5-one

SMILES

CC12CC[C@@H](OO)C(C1)=CC[C@@H]1[C@H](OC(=O)C1=C)[C@@H]2O

InChI Identifier

InChI=1S/C15H20O5/c1-8-10-4-3-9-7-15(2,6-5-11(9)20-18)13(16)12(10)19-14(8)17/h3,10-13,16,18H,1,4-7H2,2H3/b9-3+/t10-,11+,12-,13-,15?/m0/s1

InChI Key

JXXWNBNYEWOORY-BASWEGAOSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Hydroperoxide
Secondary alcohol
Carboxylic acid derivative
Peroxol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Alkyl hydroperoxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
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	4.14 g/L	ALOGPS
logP	1.21	ALOGPS
logP	1.76	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.4 m³·mol⁻¹	ChemAxon
Polarizability	28.77 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	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zg0-1940000000-e030fc44b3940015343a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0079-6869000000-00cea548e2553bbd24c5	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	splash10-001i-0090000000-ff4cd129993fc0e1342b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06sr-0290000000-c7473c8da004393f2239	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-3940000000-7f232a2cb895b35704c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-992a143d3eb7244d48b3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ti-0090000000-2e6408dd809d549b8bf4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zfs-9060000000-efe75263a4b311ebb0b5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-2cb14853e10b3483a75b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0090000000-3487fc3ae6103a394c4a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-1960000000-bb191514460e9a8bec1a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-043a95ec3a9c60d0d2b5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-0090000000-610032dcf8bf88ba5792	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00l7-0190000000-fd68ff99a61f624b358e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum