Doxorubicin citrateProduct ingredient for Doxorubicin

Name
Doxorubicin citrate
Drug Entry
Doxorubicin

Doxorubicin is a cytotoxic anthracycline antibiotic isolated from cultures of Streptomyces peucetius var. caesius. Doxorubicin binds to nucleic acids, presumably by specific intercalation of the planar anthracycline nucleus with the DNA double helix.

Accession Number
DBSALT002287
Structure
Thumb
Synonyms
Not Available
UNII
AJQ2ZNG2WL
CAS Number
111266-55-8
Weight
Average: 735.648
Monoisotopic: 735.201063355
Chemical Formula
C33H37NO18
InChI Key
INEKNBHAPBIAFK-RUELKSSGSA-N
InChI
InChI=1S/C27H29NO11.C6H8O7/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t10-,13-,15-,17-,22+,27-;/m0./s1
IUPAC Name
(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione; 2-hydroxypropane-1,2,3-tricarboxylic acid
SMILES
OC(=O)CC(O)(CC(O)=O)C(O)=O.COC1=C2C(=O)C3=C(O)C4=C(C[C@](O)(C[C@@H]4O[C@H]4C[C@H](N)[C@H](O)[C@H](C)O4)C(=O)CO)C(O)=C3C(=O)C2=CC=C1
External Links
ChemSpider
29369350
Predicted Properties
PropertyValueSource
Water Solubility1.18 mg/mLALOGPS
logP1.41ALOGPS
logP0.53ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)8ChemAxon
pKa (Strongest Basic)9.93ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area206.07 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity134.59 m3·mol-1ChemAxon
Polarizability53.84 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon