ContaminantDB: Proscillaridin

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

Record Information

Version

1.0

Creation Date

2016-05-22 03:45:33 UTC

Update Date

2016-11-09 01:15:29 UTC

Accession Number

CHEM016852

Identification

Common Name

Proscillaridin

Class

Small Molecule

Description

Proscillaridin is a cardiac glycoside that is derived from plants of the genus Scilla and in Drimia maritima (Scilla maritima). Studies suggest the potential cytotoxic and anticancer property of proscillaridin, based on evidence of the drug potently disrupting topoisomerase I and II activity at nanomolar drug concentrations [A27193] and triggering cell death and blocking cell proliferation of glioblastoma cell lines [A27194].

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
a-32686Proscillaridin	ChEMBL
2936Tradenal	ChEMBL
Abbott brand OF proscillaridin	MeSH
Knoll brand OF proscillaridin	MeSH
Proscillaridin	MeSH
Desglucotransvaaline	MeSH
Caradrin	MeSH
Digitalysat	MeSH
Rhamnoside, scillarenin	MeSH
Talusin	MeSH
Proscillaridin a	MeSH
Sandoscill	MeSH
Scillarenin rhamnoside	MeSH
Scillase	MeSH
Ysatfabrik brand OF proscillaridin	MeSH
Ziethen brand OF proscillaridin	MeSH
a, Proscillaridin	MeSH
Proscillaridine	MeSH

Chemical Formula

C₃₀H₄₂O₈

Average Molecular Mass

530.658 g/mol

Monoisotopic Mass

530.288 g/mol

CAS Registry Number

466-06-8

IUPAC Name

5-[(1S,2R,5S,10R,11S,14S,15R)-11-hydroxy-2,15-dimethyl-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-2H-pyran-2-one

Traditional Name

proscillaridin

SMILES

[H][C@@]1(CC[C@]2(O)[C@]3([H])CCC4=C[C@]([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@]1([H])O[C@@]([H])(C)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O)C1=COC(=O)C=C1

InChI Identifier

InChI=1S/C30H42O8/c1-16-24(32)25(33)26(34)27(37-16)38-19-8-11-28(2)18(14-19)5-6-22-21(28)9-12-29(3)20(10-13-30(22,29)35)17-4-7-23(31)36-15-17/h4,7,14-16,19-22,24-27,32-35H,5-6,8-13H2,1-3H3/t16-,19-,20+,21-,22+,24-,25+,26+,27-,28-,29+,30-/m0/s1

InChI Key

MYEJFUXQJGHEQK-ALRJYLEOSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Bufanolides and derivatives

Alternative Parents

Substituents

Bufanolide-skeleton
Steroidal glycoside
14-hydroxysteroid
Hydroxysteroid
Delta-4-steroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Pyranone
Pyran
Oxane
Monosaccharide
Tertiary alcohol
Cyclic alcohol
Heteroaromatic compound
Secondary alcohol
Lactone
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.043 g/L	ALOGPS
logP	2.37	ALOGPS
logP	2.3	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.22	ChemAxon
pKa (Strongest Basic)	0.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	140.05 m³·mol⁻¹	ChemAxon
Polarizability	58.26 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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02ua-0009150000-adffca2b5f77e13c458d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014r-0319000000-c1383f25e97fbeba5fee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014r-1609000000-6a08da2dbb73f9f79a2b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00pi-2108290000-c8f07e67106a8f07b38f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0159-1109010000-5a663d18d5f6704ef419	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00sr-2009000000-19c271b37c5c0add6396	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

DB13307

HMDB ID

Not Available

FooDB ID

Not Available

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

Proscillaridin

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

5284613

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Proscillaridin (CHEM016852)

Structure for CHEM016852: Proscillaridin