Colcemid (CHEM016269)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:25:18 UTC
Update Date2016-11-09 01:15:22 UTC
Accession NumberCHEM016269
Identification
Common NameColcemid
ClassSmall Molecule
DescriptionA secondary amino compound that is (S)-colchicine in which the N-acetyl group is replaced by an N-methyl group. Isolable from the autumn crocus, Colchicum autumnale, it is less toxic than colchicine and is used as an antineoplastic.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-ColchamineChEBI
ColcemidChEBI
DemecolcinaChEBI
DemecolcinumChEBI
N-Deacetyl-N-methylcolchicineChEBI
N-Desacetyl-N-methylcolchicineChEBI
N-Methyl-N-deacetylcolchicineChEBI
N-Methyl-N-desacetylcolchicineChEBI
Reichstein's FChEBI
Santavy's substance FChEBI
DemecolcineChEBI
Demecolcine, (+-)-isomerMeSH
ColcemideMeSH
ColchamineMeSH
Chemical FormulaC21H25NO5
Average Molecular Mass371.433 g/mol
Monoisotopic Mass371.173 g/mol
CAS Registry Number477-30-5
IUPAC Name(10S)-3,4,5,14-tetramethoxy-10-(methylamino)tricyclo[9.5.0.0²,⁷]hexadeca-1(16),2,4,6,11,14-hexaen-13-one
Traditional Namecolcemid
SMILES[H][C@@]1(CCC2=CC(OC)=C(OC)C(OC)=C2C2=CC=C(OC)C(=O)C=C12)NC
InChI IdentifierInChI=1S/C21H25NO5/c1-22-15-8-6-12-10-18(25-3)20(26-4)21(27-5)19(12)13-7-9-17(24-2)16(23)11-14(13)15/h7,9-11,15,22H,6,8H2,1-5H3/t15-/m0/s1
InChI KeyNNJPGOLRFBJNIW-HNNXBMFYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tropones. Tropones are compounds containing a tropone ring, which is a cycloheptatrienone ring bearing a ketone group.
KingdomOrganic compounds
Super ClassHydrocarbon derivatives
ClassTropones
Sub ClassNot Available
Direct ParentTropones
Alternative Parents
Substituents
  • Anisole
  • Tropone
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • Cyclic ketone
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
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 Solubility0.032 g/LALOGPS
logP2.52ALOGPS
logP2.08ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)16.96ChemAxon
pKa (Strongest Basic)9.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.02 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity106.71 m³·mol⁻¹ChemAxon
Polarizability40.25 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03dj-1492000000-9f8537d47622417c429dSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03dj-1492000000-9f8537d47622417c429dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-1f6ddc8c3363ad6a5e35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0009000000-ae75b1400501b9297fd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-0194000000-6f0baeb765b5d92eb6dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-ed8c1a1821d8c5705282Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0009000000-aa4e7b5666cfdcfd354dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0i7l-3092000000-52f10777fa69e59d89a0Spectrum
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 IDDB13318
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00027138
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDemecolcine
Chemspider IDNot Available
ChEBI ID4393
PubChem Compound ID220401
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=1061646
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20082301
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22394737
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2329167
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=2977921
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=7237451
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=7720099
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=7887202