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Chemistry

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Also known as: Daunoxome, Daunorubicin citrate [mart.], Daunorubicin liposomal, 371770-68-2, Daunorubicin (citrate), Daunorubicin citrate [orange book]

Molecular Formula

C₃₃H₃₇NO₁₇

Molecular Weight

719.6 g/mol

InChI Key

VNTHYLVDGVBPOU-QQYBVWGSSA-N

FDA UNII

5L84T2Z6NP

Daunorubicin Citrate is a semi-synthetic anthracycline glycoside antibiotic obtained from Streptomyces with antineoplastic activity. Daunorubicin citrate intercalates DNA, which leads to inhibition of DNA and RNA synthesis, and consequently blocks cell division and results in apoptosis. This anti-tumor antibiotic is most active in the S phase of cell division. Daunorubicin is indicated in the treatment of a wide variety of cancers including acute non-lymphocytic leukemia, non-Hodgkin lymphomas, Ewing's sarcoma, Wilms' tumor, and chronic myelocytic leukemia. (NCI05)

1 2D Structure

Daunorubicin Citrate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;2-hydroxypropane-1,2,3-tricarboxylic acid

2.1.2 InChI

InChI=1S/C27H29NO10.C6H8O7/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t10-,14-,16-,17-,22+,27-;/m0./s1

2.1.3 InChI Key

VNTHYLVDGVBPOU-QQYBVWGSSA-N

2.1.4 Canonical SMILES

CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)N)O.C(C(=O)O)C(CC(=O)O)(C(=O)O)O

2.1.5 Isomeric SMILES

C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)N)O.C(C(=O)O)C(CC(=O)O)(C(=O)O)O

2.2 Other Identifiers

2.2.1 UNII

5L84T2Z6NP

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Daunoxome

2. Daunorubicin Citrate [mart.]

3. Daunorubicin Liposomal

4. 371770-68-2

5. Daunorubicin (citrate)

6. Daunorubicin Citrate [orange Book]

7. Daunorubicin Citrate Liposome

8. 5l84t2z6np

9. Daunoxome (tn)

10. (7s,9s)-9-acetyl-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;2-hydroxypropane-1,2,3-tricarboxylic Acid

11. Unii-5l84t2z6np

12. Schembl42311

13. Chembl1200475

14. Dtxsid20190659

15. Daunorubicin Citrate [who-dd]

16. 5,12-naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8s,10s)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

17. 5,12-naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8s,10s)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1) (salt)

18. Hy-108876

19. Cs-0031208

20. Daunorubicin Citrate Liposome [vandf]

21. D10787

22. Q27262517

23. 5,12-naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8s,10s)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

24. 5,12-naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8s,10s)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1) (salt)

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₃₃H₃₇NO₁₇
Molecular Weight	719.6 g/mol
Hydrogen Bond Donor Count	9
Hydrogen Bond Acceptor Count	18
Rotatable Bond Count	9
Exact Mass	719.20614871 g/mol
Monoisotopic Mass	719.20614871 g/mol
Topological Polar Surface Area	318 Å²
Heavy Atom Count	51
Formal Charge	0
Complexity	1190
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2