(2S)-N-[(2S,3S,4S,6R)-6-{[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-4-methylpentanamido]propanamido]-4-methylpentanamide hydrochloride

• ChemBase ID: 159606
• Molecular Formular: C45H62ClN5O14
• Molecular Mass: 932.45188
• Monoisotopic Mass: 931.39817937
• SMILES: c1cc(c2c(c1)C(=O)c1c(C2=O)c(c2c(c1O)C[C@@](C[C@@H]2O[C@H]1C[C@H]([C@@H]([C@@H](O1)C)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)C)CC(C)C)C)CC(C)C)(O)C(=O)C)O)OC.Cl
• Canonical SMILES: COc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)[C@@H](O[C@@H]1O[C@@H](C)[C@H]([C@@H](C1)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)C)CC(C)C)C)CC(C)C)O)C[C@](C2)(O)C(=O)C.Cl
• InChI: InChI=1S/C45H61N5O14.ClH/c1-18(2)13-27(49-41(57)20(5)46)43(59)47-21(6)42(58)50-28(14-19(3)4)44(60)48-26-15-31(63-22(7)36(26)52)64-30-17-45(61,23(8)51)16-25-33(30)40(56)35-34(38(25)54)37(53)24-11-10-12-29(62-9)32(24)39(35)55;/h10-12,18-22,26-28,30-31,36,52,54,56,61H,13-17,46H2,1-9H3,(H,47,59)(H,48,60)(H,49,57)(H,50,58);1H/t20-,21-,22-,26-,27-,28-,30-,31-,36+,45-;/m0./s1
• InChIKey: LJWJYPAQXONXEF-SKQXRMJDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(2S,3S,4S,6R)-6-{[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-4-methylpentanamido]propanamido]-4-methylpentanamide hydrochloride
• IUPAC Traditional name: (2S)-N-[(2S,3S,4S,6R)-6-{[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-4-methylpentanamido]propanamido]-4-methylpentanamide hydrochloride
• Synonyms: Ala-Leu-Ala-Leu-DNR; Ala-Leu-Ala-Leu Daunorubicin Hydrochloride; (8S-cis)-8-Acetyl-10-[[3-[[N-[N-(N-L-alanyl-L-leucyl)-L-alanyl]-L-leucyl]amino]-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione Monohydrochloride

Database IDs

• CAS Number: 76582-70-2
• PubChem SID: 162253741
• PubChem CID: 71313059

CALCULATED PROPERTIES

• Acid pKa: 9.250181
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): 0.23107204
• LogD (pH = 7.4): 1.9147527
• Log P: 2.4333994
• Molar Refractivity: 229.4283 cm^3
• Polarizability: 90.07555 Å^3
• Polar Surface Area: 302.24 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A470300

Daunorubicin linked to proteins shows antitumor activity; prodrug Daunorubicin (D194500) peptide tumor.

REFERENCES

• Ginsburg, G., et al.: J. Biol. Chem., 259, 6667 (1984)
• de Smidt, P., et al.: Cancer Res., 50, 7476 (1984)
• de Smidt, P., et al.: Biochem., 32, 2916 (1984)