2-oxo-2-[(2S,4S)-2,5,12-trihydroxy-4-{[5-hydroxy-6-methyl-4-(trifluoroacetamido)oxan-2-yl]oxy}-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl pentanoate

• ChemBase ID: 269
• Molecular Formular: C34H36F3NO13
• Molecular Mass: 723.6437496
• Monoisotopic Mass: 723.21387488
• SMILES: FC(F)(F)C(=O)NC1CC(O[C@H]2C[C@@](O)(Cc3c2c(O)c2c(c3O)C(=O)c3c(C2=O)c(OC)ccc3)C(=O)COC(=O)CCCC)OC(C1O)C
• Canonical SMILES: CCCCC(=O)OCC(=O)[C@@]1(O)C[C@H](OC2CC(NC(=O)C(F)(F)F)C(C(O2)C)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC
• InChI: InChI=1S/C34H36F3NO13/c1-4-5-9-21(40)49-13-20(39)33(47)11-16-24(19(12-33)51-22-10-17(27(41)14(2)50-22)38-32(46)34(35,36)37)31(45)26-25(29(16)43)28(42)15-7-6-8-18(48-3)23(15)30(26)44/h6-8,14,17,19,22,27,41,43,45,47H,4-5,9-13H2,1-3H3,(H,38,46)/t14?,17?,19-,22?,27?,33-/m0/s1
• InChIKey: ZOCKGBMQLCSHFP-ZQUOIQDWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-oxo-2-[(2S,4S)-2,5,12-trihydroxy-4-{[5-hydroxy-6-methyl-4-(trifluoroacetamido)oxan-2-yl]oxy}-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl pentanoate
• IUPAC Traditional name: valtaxin
• Brand Name: Valstar; Valstar Preservative Free
• Synonyms: Antibiotic Ad 32; Valrubicin

Database IDs

• CAS Number: 56124-62-0
• PubChem SID: 46506642; 160963732
• PubChem CID: 41744

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.3934793
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): 4.1876435
• LogD (pH = 7.4): 3.5702426
• Log P: 4.486147
• Molar Refractivity: 168.0281 cm^3
• Polarizability: 64.89921 Å^3
• Polar Surface Area: 215.22 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.67
• LOG S: -4.35
• Solubility (Water): 3.25e-02 g/l

PROPERTIES

Physical Property

• Solubility: insoluble
• Hydrophobicity(logP): 2.2

DETAILS

DrugBank - DB00385

• Drug Groups: approved
• Description: Valrubicin (N-trifluoroacetyladriamycin-14-valerate, Valstar®) is a chemotherapy drug used to treat bladder cancer. Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder. [Wikipedia]
• Indication: For the treatment of cancer of the bladder.
• Pharmacology: Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder.
• Toxicity: The primary anticipated complications of overdosage associated with intravesical administration would be consistent with irritable bladder symptoms. Myelosuppression is possible if valrubicin is inadvertently administered systemically or if significant systemic exposure occurs following intravesical administration (e.g., in patients with bladder/rupture perforation). The maximum tolerated dose in humans by either intraperitoneal or intravenous administration is 600 mg/m^2.
• Affected Organisms: Humans and other mammals
• Biotransformation: Valrubicin is metabolized to two primary metabolites: N-trifluoroacetyladriamycin and N-trifluoroacetyladriamycinol.
• Protein Binding: >99%
• External Links: Wikipedia; RxList; Drugs.com