Castanospermine

Identification

Name
Castanospermine
Accession Number
DB01816  (EXPT01055)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • (1S-(1α,6β,7α,8β,8αβ))-octahydro-1,6,7,8-indolizinetetrol
  • (1S,6S,7R,8R,8aR)-1,6,7,8-tetrahydroxyindolizidine
  • 1,6,7,8-tetrahydroxyoctahydroindolizine
Categories
UNII
Q0I3184XM7
CAS number
79831-76-8
Weight
Average: 189.209
Monoisotopic: 189.100107973
Chemical Formula
C8H15NO4
InChI Key
JDVVGAQPNNXQDW-TVNFTVLESA-N
InChI
InChI=1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1
IUPAC Name
(1S,6S,7R,8R,8aR)-octahydroindolizine-1,6,7,8-tetrol
SMILES
[H][C@]1(O)CCN2C[C@]([H])(O)[C@@]([H])(O)[C@]([H])(O)[C@@]12[H]

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlucan 1,3-beta-glucosidaseNot AvailableYeast
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
(4R)-limoneneThe risk or severity of adverse effects can be increased when Castanospermine is combined with (4R)-limonene.
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when Castanospermine is combined with 16-Bromoepiandrosterone.
19-norandrostenedioneThe risk or severity of adverse effects can be increased when Castanospermine is combined with 19-norandrostenedione.
5-androstenedioneThe risk or severity of adverse effects can be increased when Castanospermine is combined with 5-androstenedione.
AceclofenacThe risk or severity of adverse effects can be increased when Castanospermine is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Castanospermine is combined with Acemetacin.
AdalimumabThe risk or severity of adverse effects can be increased when Adalimumab is combined with Castanospermine.
AlclofenacThe risk or severity of adverse effects can be increased when Castanospermine is combined with Alclofenac.
AlclometasoneThe risk or severity of adverse effects can be increased when Castanospermine is combined with Alclometasone.
AldesleukinThe risk or severity of adverse effects can be increased when Castanospermine is combined with Aldesleukin.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C02256
PubChem Compound
54445
PubChem Substance
46507978
ChemSpider
49177
BindingDB
36388
ChEBI
27860
ChEMBL
CHEMBL311226
HET
CTS
Wikipedia
Castanospermine
PDB Entries
1eqc / 2cbu / 2jkp / 2pwg / 2vl8 / 4iif / 5ied

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
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1110.0 mg/mLALOGPS
logP-2.1ALOGPS
logP-2.6ChemAxon
logS0.77ALOGPS
pKa (Strongest Acidic)12.89ChemAxon
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area84.16 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.44 m3·mol-1ChemAxon
Polarizability18.72 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8918
Blood Brain Barrier-0.603
Caco-2 permeable-0.5805
P-glycoprotein substrateSubstrate0.6783
P-glycoprotein inhibitor INon-inhibitor0.8961
P-glycoprotein inhibitor IINon-inhibitor0.9806
Renal organic cation transporterNon-inhibitor0.6639
CYP450 2C9 substrateNon-substrate0.8783
CYP450 2D6 substrateNon-substrate0.6942
CYP450 3A4 substrateSubstrate0.5188
CYP450 1A2 substrateNon-inhibitor0.8141
CYP450 2C9 inhibitorNon-inhibitor0.9406
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.939
CYP450 3A4 inhibitorNon-inhibitor0.9974
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9942
Ames testNon AMES toxic0.7775
CarcinogenicityNon-carcinogens0.9757
BiodegradationNot ready biodegradable0.9638
Rat acute toxicity2.3961 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6611
hERG inhibition (predictor II)Non-inhibitor0.9173
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-00o0-1932000000-28a09bc636766bb094b0
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-3900000000-75396d0a5940c9e29a57
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-006x-2900000000-079bdf1716f2d906311b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-02ms-9800000000-e528e43709795f6c7798
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-030r-9200000000-8d9a667a9121223e0f3e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00lr-9000000000-1798e7ef1f3d1099d86d

Taxonomy

Description
This compound belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indolizidines
Sub Class
Not Available
Direct Parent
Indolizidines
Alternative Parents
Piperidines / N-alkylpyrrolidines / Trialkylamines / Secondary alcohols / 1,2-aminoalcohols / Polyols / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Indolizidine / Piperidine / N-alkylpyrrolidine / Pyrrolidine / Tertiary aliphatic amine / Tertiary amine / Secondary alcohol / 1,2-aminoalcohol / Azacycle / Polyol
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
indolizidine alkaloid (CHEBI:27860) / Indolizidine alkaloids (C02256)

Targets

Kind
Protein
Organism
Yeast
Pharmacological action
Unknown
General Function
Transferase activity
Specific Function
Major glucan 1,3-beta-glucosidase required for cell wall integrity. Beta-glucanases participate in the metabolism of beta-glucan, the main structural component of the cell wall. Can also function b...
Gene Name
XOG1
Uniprot ID
P29717
Uniprot Name
Glucan 1,3-beta-glucosidase
Molecular Weight
50037.635 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on August 02, 2018 04:41