(10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-8-propanoyl-5,7,8,9,10,12-hexahydrotetracene-5,12-dione hydrochloride

• ChemBase ID: 175746
• Molecular Formular: C28H32ClNO10
• Molecular Mass: 578.00738
• Monoisotopic Mass: 577.17147391
• SMILES: c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1O)CC(C[C@@H]2O[C@@H]1O[C@H]([C@@H](O)[C@H](N)C1)C)(C(=O)CC)O)O)OC.Cl
• Canonical SMILES: CCC(=O)C1(O)C[C@H](O[C@H]2C[C@@H](N)[C@@H]([C@@H](O2)C)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC.Cl
• InChI: InChI=1S/C28H31NO10.ClH/c1-4-17(30)28(36)9-13-20(16(10-28)39-18-8-14(29)23(31)11(2)38-18)27(35)22-21(25(13)33)24(32)12-6-5-7-15(37-3)19(12)26(22)34;/h5-7,11,14,16,18,23,31,33,35-36H,4,8-10,29H2,1-3H3;1H/t11-,14-,16-,18-,23+,28?;/m0./s1
• InChIKey: IRYNIMWZWIUFRG-BVMYRDFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-8-propanoyl-5,7,8,9,10,12-hexahydrotetracene-5,12-dione hydrochloride
• IUPAC Traditional name: (10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-8-propanoyl-9,10-dihydro-7H-tetracene-5,12-dione hydrochloride
• Synonyms: 10-[(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-8-(1-oxopropyl)-5,12-naphthacenedione Hydrochloride; NSC 279509

Database IDs

• CAS Number: 68674-19-1
• PubChem SID: 164231656
• PubChem CID: 71751267

CALCULATED PROPERTIES

• Acid pKa: 9.530935
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): 0.07490908
• LogD (pH = 7.4): 1.2422209
• Log P: 2.4342275
• Molar Refractivity: 137.5184 cm^3
• Polarizability: 53.852165 Å^3
• Polar Surface Area: 185.84 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N900400

A Daunorubicin analogue with novel 9-Acyl substituent. Antineoplastic.

REFERENCES

• Tong, G., et al.: J. Med. Chem., 19, 395 (1976)
• Penco, S., et al.: J. Antibiot., 30, 761 (1976)