Flavopiridol hydrochloride (CHEM020177)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:53:01 UTC
Update Date2016-11-09 01:16:09 UTC
Accession NumberCHEM020177
Identification
Common NameFlavopiridol hydrochloride
ClassSmall Molecule
DescriptionA hydrochloride salt resulting from the formal reaction of equimolar amounts of alvocidib and hydrogen chloride. A cyclin-dependent kinase 9 (CDK9) inhibitor, it has been studied for the treatment of acute myeloid leukaemia, arthritis and atherosclerotic plaque formation.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3S,4R)-4-[2-(2-Chlorophenyl)-5,7-dihydroxy-4-oxo-4H-chromen-8-yl]-3-hydroxy-1-methylpiperidinium chlorideChEBI
Alvocidib HCLChEBI
HL 275ChEBI
HL-275ChEBI
HMR 1275ChEBI
HMR-1275ChEBI
L 86 8275ChEBI
L86-8275ChEBI
AlvocidibMeSH
FlavopiridolMeSH
(-)cis-5,7-Dihydroxy-2-(2-chlorophenyl)-8-(4-(3-hydroxy-1-methyl)piperidinyl)-4H-1-benzopyran-4-oneMeSH
Chemical FormulaC21H21Cl2NO5
Average Molecular Mass438.301 g/mol
Monoisotopic Mass437.080 g/mol
CAS Registry Number131740-09-5
IUPAC Name2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-4H-chromen-4-one hydrochloride
Traditional Nameflavopiridol hydrochloride
SMILESCl.[H][C@@]1(O)CN(C)CC[C@]1([H])C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC=CC=C1Cl
InChI IdentifierInChI=1S/C21H20ClNO5.ClH/c1-23-7-6-12(17(27)10-23)19-14(24)8-15(25)20-16(26)9-18(28-21(19)20)11-4-2-3-5-13(11)22;/h2-5,8-9,12,17,24-25,27H,6-7,10H2,1H3;1H/t12-,17+;/m0./s1
InChI KeyLGMSNQNWOCSPIK-LWHGMNCYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
Substituents
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenylpiperidine
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Chlorobenzene
  • Halobenzene
  • Pyranone
  • Aralkylamine
  • Benzenoid
  • Pyran
  • Piperidine
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Hydrochloride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.094 g/LALOGPS
logP2.81ALOGPS
logP2.48ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.71ChemAxon
pKa (Strongest Basic)7.36ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity107.74 m³·mol⁻¹ChemAxon
Polarizability40.66 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-827dd2143560ad1a3d84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000900000-827dd2143560ad1a3d84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0000900000-827dd2143560ad1a3d84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-4daedc3c2bba43d6834aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000900000-4daedc3c2bba43d6834aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0000900000-4daedc3c2bba43d6834aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT000800
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID90998
PubChem Compound ID9910986
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1279187
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21541623
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21556497
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=8002990
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=8250970
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=9269999
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=9815683