ContaminantDB: Physangulide

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

Record Information

Version

1.0

Creation Date

2016-05-26 02:14:38 UTC

Update Date

2016-11-09 01:19:09 UTC

Accession Number

CHEM030892

Identification

Common Name

Physangulide

Class

Small Molecule

Description

Constituent of the famine food Physalis angulata (cutleaf ground cherry). Physangulide is found in herbs and spices and fruits.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5b,6b-Epoxy-3b,4b,20R,24S,25R-pentahydroxy-1-oxo-22S-withanolide	HMDB

Chemical Formula

C₂₈H₄₂O₉

Average Molecular Mass

522.628 g/mol

Monoisotopic Mass

522.283 g/mol

CAS Registry Number

131749-58-1

IUPAC Name

15-[1-(4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one

Traditional Name

15-[1-(4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl)-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one

SMILES

CC(O)(C1CCC2C3CC4OC44C(O)C(O)CC(=O)C4(C)C3CCC12C)C1CC(C)(O)C(C)(O)C(=O)O1

InChI Identifier

InChI=1S/C28H42O9/c1-23-9-8-15-13(10-19-28(37-19)21(31)16(29)11-18(30)25(15,28)3)14(23)6-7-17(23)26(4,34)20-12-24(2,33)27(5,35)22(32)36-20/h13-17,19-21,29,31,33-35H,6-12H2,1-5H3

InChI Key

OREAQOXKZSQPCV-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
5,6-epoxysteroid
Delta valerolactone
Delta_valerolactone
Oxepane
Oxane
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Ketone
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
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	0.39 g/L	ALOGPS
logP	1.17	ALOGPS
logP	0.53	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.5	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	157.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	129.57 m³·mol⁻¹	ChemAxon
Polarizability	56 Å³	ChemAxon
Number of Rings	6	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	splash10-0udi-2211920000-fc349febaff27a7be0eb	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0f6x-5200279000-66d4c2a47f1f61db2d28	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-0001290000-48175308663779431b90	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pi0-0139260000-5adb16915aeab94b87c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0019300000-2dedfa8e42caecabbd15	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0001390000-7c2796566b6b44151f32	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uxr-4369670000-65bc7723da7b95339aa6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0wmr-5309100000-b7097666778a8d0bdac2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0003290000-93e26a4574b865e5d84e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06xt-0319350000-52e71dad6f71c46eefc6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0396200000-67594fb2764d40165776	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00fr-0000590000-2700ebde79dd57adf138	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-2001790000-35fdfb39b6841c150361	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ot-1009000000-b369d425693a20ca47fa	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

HMDB0037381

FooDB ID

FDB016419

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

14605176

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

Physangulide (CHEM030892)

Structure for CHEM030892: Physangulide