ContaminantDB: alpha-Peroxyachifolide

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

Record Information

Version

1.0

Creation Date

2016-05-26 03:47:11 UTC

Update Date

2016-11-09 01:20:48 UTC

Accession Number

CHEM032903

Identification

Common Name

alpha-Peroxyachifolide

Class

Small Molecule

Description

Constituent of Achillea millefolium (yarrow). alpha-Peroxyachifolide is found in herbs and spices.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
a-Peroxyachifolide	Generator
Α-peroxyachifolide	Generator
3-Hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.0¹,¹⁰.0⁵,⁹]pentadec-14-en-2-yl (2E)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₄O₇

Average Molecular Mass

376.400 g/mol

Monoisotopic Mass

376.152 g/mol

CAS Registry Number

Not Available

IUPAC Name

3-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.0¹,¹⁰.0⁵,⁹]pentadec-14-en-2-yl (2E)-2-methylbut-2-enoate

Traditional Name

3-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.0¹,¹⁰.0⁵,⁹]pentadec-14-en-2-yl (2E)-2-methylbut-2-enoate

SMILES

[H][C@@]12[C@H]3OC(=O)C(=C)[C@@H]3C[C@@H](O)[C@@](C)(OC(=O)C(\C)=C\C)[C@@]11OO[C@]2(C)C=C1

InChI Identifier

InChI=1S/C20H24O7/c1-6-10(2)16(22)25-19(5)13(21)9-12-11(3)17(23)24-14(12)15-18(4)7-8-20(15,19)27-26-18/h6-8,12-15,21H,3,9H2,1-2,4-5H3/b10-6+/t12-,13+,14-,15-,18+,19+,20-/m0/s1

InChI Key

UMHHYRUGXILZJB-ISOVPUPJSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Not Available

Substituents

Not Available

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	0.55 g/L	ALOGPS
logP	2.07	ALOGPS
logP	2.72	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.42 m³·mol⁻¹	ChemAxon
Polarizability	38.41 Å³	ChemAxon
Number of Rings	4	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	splash10-0a4i-7972000000-50778938dfa5b0523b4b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0a59-9433100000-05846f396ba75e57d738	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	splash10-004i-2029000000-1502cefb668ef6c8f5de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a7i-9025000000-a70fa9bde2bc7aef7b0a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pc0-9120000000-b44ebbe0e9b2267d2da9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1019000000-d0ef4df4cc6ea1191acd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-055b-9047000000-47e3398aeb9bebc148b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9120000000-b3e32d7fad70175ecc26	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0091000000-185d06176782a65f4646	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a7i-2293000000-d024b71faedfc880d5db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-5292000000-65d1476094cda95e4879	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-4093000000-89893d5534f13c22fb2d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0090000000-5db4973951919bf1e800	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-9010000000-80c369e0cb20da3bfba0	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0039575

FooDB ID

FDB019197

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

131752683

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.

2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.

3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.

4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.

5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

6. The lipid handbook with CD-ROM

alpha-Peroxyachifolide (CHEM032903)

Structure for CHEM032903: alpha-Peroxyachifolide