3''-(Beta-Chloroethyl)-2'',4''-Dioxo-3, 5''-Spiro-Oxazolidino-4-Deacetoxy-Vinblastine

Identification

Name
3''-(Beta-Chloroethyl)-2'',4''-Dioxo-3, 5''-Spiro-Oxazolidino-4-Deacetoxy-Vinblastine
Accession Number
DB02868  (EXPT01963)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
6PBV11IO5E
CAS number
Not Available
Weight
Average: 826.419
Monoisotopic: 825.386826878
Chemical Formula
C46H56ClN5O7
InChI Key
NUXKIZBEPYVRKP-RWBWKAGLSA-N
InChI
InChI=1S/C46H56ClN5O7/c1-6-42-14-10-17-51-19-15-44(37(42)51)31-21-32(35(57-4)22-34(31)49(3)38(44)46(26-42)39(53)52(20-16-47)41(55)59-46)45(40(54)58-5)24-28-23-43(56,7-2)27-50(25-28)18-13-30-29-11-8-9-12-33(29)48-36(30)45/h8-12,14,21-22,28,37-38,48,56H,6-7,13,15-20,23-27H2,1-5H3/t28-,37-,38+,42-,43-,44+,45-,46+/m0/s1
IUPAC Name
methyl (13S,15R,17S)-13-[(1'R,2R,9'R,12'R,19'S)-4-(2-chloroethyl)-12'-ethyl-5'-methoxy-8'-methyl-3,5-dioxo-8',16'-diazaspiro[1,4-oxazolidine-2,10'-pentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadecane]-2',4',6',13'-tetraen-4'-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate
SMILES
[H][[email protected]@]12N(C)C3=CC(OC)=C(C=C3[[email protected]@]11CCN3CC=C[[email protected]@](CC)(C[[email protected]@]22OC(=O)N(CCCl)C2=O)[[email protected]@]13[H])[[email protected]]1(C[[email protected]@]2([H])CN(C[[email protected]](O)(CC)C2)CCC2=C1NC1=CC=CC=C21)C(=O)OC

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCalmodulinNot AvailableHuman
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
157684
PubChem Substance
46504738
ChemSpider
138752
HET
KAR
PDB Entries
1xa5

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 Solubility0.00934 mg/mLALOGPS
logP5.05ALOGPS
logP5.72ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)14.41ChemAxon
pKa (Strongest Basic)8.97ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area127.88 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity226.28 m3·mol-1ChemAxon
Polarizability89.03 Å3ChemAxon
Number of Rings10ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier-0.8722
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.8653
P-glycoprotein inhibitor IInhibitor0.6988
P-glycoprotein inhibitor IIInhibitor0.8007
Renal organic cation transporterNon-inhibitor0.88
CYP450 2C9 substrateNon-substrate0.7654
CYP450 2D6 substrateNon-substrate0.8895
CYP450 3A4 substrateSubstrate0.7913
CYP450 1A2 substrateNon-inhibitor0.8698
CYP450 2C9 inhibitorNon-inhibitor0.7113
CYP450 2D6 inhibitorNon-inhibitor0.8468
CYP450 2C19 inhibitorNon-inhibitor0.6922
CYP450 3A4 inhibitorInhibitor0.8095
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7418
Ames testNon AMES toxic0.7576
CarcinogenicityNon-carcinogens0.8276
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.8843 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9404
hERG inhibition (predictor II)Inhibitor0.5
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
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 vinca alkaloids. These are alkaloids with a dimeric chemical structure composed of an indole nucleus (catharanthine), and a dihydroindole nucleus (vindoline), joined together.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Vinca alkaloids
Sub Class
Not Available
Direct Parent
Vinca alkaloids
Alternative Parents
Carbazoles / 3-alkylindoles / Dialkylarylamines / Anisoles / Aralkylamines / Oxazolidinediones / Alkyl aryl ethers / Piperidines / N-alkylpyrrolidines / Carbamate esters
show 17 more
Substituents
Vinca alkaloid skeleton / Carbazole / 3-alkylindole / Indole / Indole or derivatives / Anisole / Tertiary aliphatic/aromatic amine / Dialkylarylamine / Alkyl aryl ether / Oxazolidinedione
show 40 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Titin binding
Specific Function
Calmodulin mediates the control of a large number of enzymes, ion channels, aquaporins and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number...
Gene Name
CALM1
Uniprot ID
P0DP23
Uniprot Name
Calmodulin
Molecular Weight
16837.47 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:04