Proscillaridin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Proscillaridin
Accession Number
DB13307
Type
Small Molecule
Groups
Experimental
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 [1] and triggering cell death and blocking cell proliferation of glioblastoma cell lines [2].

Structure
Thumb
Synonyms
Not Available
External IDs
A-32686
Categories
UNII
KC6BL281EN
CAS number
466-06-8
Weight
Average: 530.658
Monoisotopic: 530.287968312
Chemical Formula
C30H42O8
InChI Key
MYEJFUXQJGHEQK-ALRJYLEOSA-N
InChI
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
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
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
10-hydroxycamptothecinProscillaridin may decrease the cardiotoxic activities of 10-hydroxycamptothecin.
2-(4-Chlorophenyl)-5-QuinoxalinecarboxamideProscillaridin may decrease the cardiotoxic activities of 2-(4-Chlorophenyl)-5-Quinoxalinecarboxamide.
2-chloroethyl-3-sarcosinamide-1-nitrosoureaProscillaridin may decrease the cardiotoxic activities of 2-chloroethyl-3-sarcosinamide-1-nitrosourea.
2-MethoxyestradiolProscillaridin may decrease the cardiotoxic activities of 2-Methoxyestradiol.
3-MethoxybenzamideProscillaridin may decrease the cardiotoxic activities of 3-Methoxybenzamide.
3,3'-diindolylmethaneProscillaridin may decrease the cardiotoxic activities of 3,3'-diindolylmethane.
3,4-Dihydroxybenzoic AcidProscillaridin may decrease the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.
6-O-benzylguanineProscillaridin may decrease the cardiotoxic activities of 6-O-benzylguanine.
7-HydroxystaurosporineProscillaridin may decrease the cardiotoxic activities of 7-Hydroxystaurosporine.
8-azaguanineProscillaridin may decrease the cardiotoxic activities of 8-azaguanine.
Food Interactions
Not Available

References

General References
  1. Bielawski K, Winnicka K, Bielawska A: Inhibition of DNA topoisomerases I and II, and growth inhibition of breast cancer MCF-7 cells by ouabain, digoxin and proscillaridin A. Biol Pharm Bull. 2006 Jul;29(7):1493-7. [PubMed:16819197]
  2. Denicolai E, Baeza-Kallee N, Tchoghandjian A, Carre M, Colin C, Jiglaire CJ, Mercurio S, Beclin C, Figarella-Branger D: Proscillaridin A is cytotoxic for glioblastoma cell lines and controls tumor xenograft growth in vivo. Oncotarget. 2014 Nov 15;5(21):10934-48. [PubMed:25400117]
External Links
PubChem Compound
5284613
PubChem Substance
347829292
ChemSpider
4447658
ChEBI
32065
ChEMBL
CHEMBL600325
Wikipedia
Proscillaridin
ATC Codes
C01AB51 — Proscillaridin, combinationsC01AB01 — Proscillaridin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0427 mg/mLALOGPS
logP2.37ALOGPS
logP2.3ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.22ChemAxon
pKa (Strongest Basic)0.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.68 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity140.05 m3·mol-1ChemAxon
Polarizability58.26 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound 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
Steroidal glycosides / 14-hydroxysteroids / Delta-4-steroids / Hexoses / O-glycosyl compounds / Pyranones and derivatives / Oxanes / Tertiary alcohols / Heteroaromatic compounds / Lactones
show 7 more
Substituents
Bufanolide-skeleton / Steroidal glycoside / 14-hydroxysteroid / Hydroxysteroid / Delta-4-steroid / Hexose monosaccharide / Glycosyl compound / O-glycosyl compound / Pyranone / Pyran
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on June 23, 2017 14:39 / Updated on August 02, 2018 06:50