ContaminantDB: 4-Deoxyphysalolactone

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

Record Information

Version

1.0

Creation Date

2016-05-26 00:25:53 UTC

Update Date

2016-11-09 01:18:41 UTC

Accession Number

CHEM028398

Identification

Common Name

4-Deoxyphysalolactone

Class

Small Molecule

Description

4-Deoxyphysalolactone is found in fruits. 4-Deoxyphysalolactone is a constituent of Physalis peruviana (Cape gooseberry)

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-chloro-5,14,17,20-Tetrahydroxy-1-oxowitha-2,24-dienolide	HMDB

Chemical Formula

C₂₈H₃₉ClO₇

Average Molecular Mass

523.058 g/mol

Monoisotopic Mass

522.238 g/mol

CAS Registry Number

78286-00-7

IUPAC Name

6-(1-{8-chloro-7,11,14-trihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one

Traditional Name

6-(1-{8-chloro-7,11,14-trihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one

SMILES

CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC(Cl)C4(O)CC=CC(=O)C4(C)C3CCC12C

InChI Identifier

InChI=1S/C28H39ClO7/c1-15-13-21(36-22(31)16(15)2)25(5,32)28(35)12-11-26(33)18-14-19(29)27(34)9-6-7-20(30)24(27,4)17(18)8-10-23(26,28)3/h6-7,17-19,21,32-35H,8-14H2,1-5H3

InChI Key

DSFWZSDSZFDOMA-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
20-hydroxysteroid
6-halo-steroid
Halo-steroid
14-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
1-oxosteroid
Oxosteroid
17-hydroxysteroid
Dihydropyranone
Cyclohexenone
Pyran
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Carboxylic acid ester
Chlorohydrin
Lactone
Ketone
Halohydrin
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Alcohol
Alkyl chloride
Organohalogen compound
Organochloride
Organooxygen compound
Organic oxide
Alkyl halide
Hydrocarbon derivative
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	0.084 g/L	ALOGPS
logP	2.28	ALOGPS
logP	2.89	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.6	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	134.97 m³·mol⁻¹	ChemAxon
Polarizability	55.24 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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	splash10-0g0b-3769210000-392de0a27af000ca9416	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0fg9-7570709000-22f771d9d29d6fb1b968	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0abi-0003490000-cf4ca959aacba9edb5ca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-9205630000-6f3d77e8dd2aab22662c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k9i-4039000000-e1be83dba74df5b25136	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0103590000-dce9586966d92ddf12d3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gbi-1907120000-8dc4851414cf03590ebf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9405000000-6b36464dc4007006eb69	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0229-0008290000-a6ce1a0705b289e2479e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-046s-2009220000-d04570919474ac2211dc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0frx-9401000000-7a067bd15a0408b10a88	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000390000-955f176170eb38c860ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-003r-9108530000-529fb1bfeac42e641667	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02ai-6797000000-21c8e78aec37afca0297	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

HMDB0034346

FooDB ID

FDB012707

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

13743195

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

4-Deoxyphysalolactone (CHEM028398)

Structure for CHEM028398: 4-Deoxyphysalolactone