Carminomycin (CHEM016608)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:38:22 UTC
Update Date2016-11-09 01:15:26 UTC
Accession NumberCHEM016608
Identification
Common NameCarminomycin
ClassSmall Molecule
DescriptionA toxic anthracycline antibiotic that is produced by Actinomadura carminata and also has potent antineoplastic activity.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CarubicinChEBI
CCRIS 961ChEBI
KarminomycinChEBI
O-DemethyldaunomycinChEBI
CarminomicinMeSH
Carminomycin IIMeSH
Hydrochloride, carubicinMeSH
Rubeomycin a1MeSH
Carminomycin IMeSH
DemethyldaunomycinMeSH
Carminomycin IIIMeSH
DemethyldaunorubicinMeSH
Rubeomycin aMeSH
Carubicin hydrochlorideMeSH
KarminomicinMeSH
Chemical FormulaC26H27NO10
Average Molecular Mass513.499 g/mol
Monoisotopic Mass513.163 g/mol
CAS Registry Number50935-04-1
IUPAC Name(8S,10S)-8-acetyl-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-1,6,8,11-tetrahydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
Traditional Namecarminomycin
SMILES[H][C@]1(N)C[C@]([H])(O[C@@]2([H])C[C@@](O)(CC3=C(O)C4=C(C(O)=C23)C(=O)C2=C(C=CC=C2O)C4=O)C(C)=O)O[C@@]([H])(C)[C@@]1([H])O
InChI IdentifierInChI=1S/C26H27NO10/c1-9-21(30)13(27)6-16(36-9)37-15-8-26(35,10(2)28)7-12-18(15)25(34)20-19(23(12)32)22(31)11-4-3-5-14(29)17(11)24(20)33/h3-5,9,13,15-16,21,29-30,32,34-35H,6-8,27H2,1-2H3/t9-,13-,15-,16-,21+,26-/m0/s1
InChI KeyXREUEWVEMYWFFA-CSKJXFQVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassAnthracyclines
Sub ClassNot Available
Direct ParentAnthracyclines
Alternative Parents
Substituents
  • Anthracycline
  • Anthracyclinone-skeleton
  • Aminoglycoside core
  • Tetracenequinone
  • 9,10-anthraquinone
  • 1,4-anthraquinone
  • Anthracene
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tetralin
  • Aryl ketone
  • Amino saccharide
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Vinylogous acid
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Ketone
  • Polyol
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Primary amine
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility1.32 g/LALOGPS
logP1.6ALOGPS
logP1.76ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)7.78ChemAxon
pKa (Strongest Basic)9.22ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area196.84 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity128.41 m³·mol⁻¹ChemAxon
Polarizability51.62 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03y1-0009640000-34d19b4f5d8c12af8e7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0319100000-ba8046944f882fb30aeaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-6239000000-14d7102b462bb57eb98aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1106490000-39f06fccf321ebc6d072Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001l-2109400000-2c91fca3d223bba58a7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3109000000-1031d4a1fb1f8e3929a9Spectrum
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 IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-15734
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCarubicin
Chemspider IDNot Available
ChEBI ID31359
PubChem Compound ID443831
Kegg Compound IDC12432
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1020931
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1020945
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1037187
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1037188
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=1101812
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=210711
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21199801
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=334058
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=350145
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=3631931
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=411416
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=629523
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=6546298
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=6582798
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=677842
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=677851
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=677854
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=6943332
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=79334
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=798543
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=883801
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=883808
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=911158
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=999239