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Also known as: 677017-23-1, Wp 769, Berubicin [inn], 6qpn83hk2m, (7s,9s)-7-[(2r,4s,5s,6s)-4-amino-6-methyl-5-phenylmethoxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione, Unii-6qpn83hk2m

Molecular Formula

C₃₄H₃₅NO₁₁

Molecular Weight

633.6 g/mol

InChI Key

FIGNGSHKNAHTSH-JJMFXPFOSA-N

FDA UNII

6QPN83HK2M

Berubicin is a 4'-O-benzylated analogue of the anthracycline derivative doxorubicin, with potential antineoplastic activity. Berubicin intercalates into DNA and interrupts topoisomerase II activity, resulting in the inhibition of DNA replication and repair, as well as RNA and protein synthesis. Unlike other anthracycline derivatives, this agent crosses the blood-brain barrier (BBB) and can circumvent P glycoprotein/MRP1-mediated efflux.

1 2D Structure

Berubicin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-phenylmethoxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione

2.1.2 InChI

InChI=1S/C34H35NO11/c1-16-33(44-15-17-7-4-3-5-8-17)20(35)11-24(45-16)46-22-13-34(42,23(37)14-36)12-19-26(22)32(41)28-27(30(19)39)29(38)18-9-6-10-21(43-2)25(18)31(28)40/h3-10,16,20,22,24,33,36,39,41-42H,11-15,35H2,1-2H3/t16-,20-,22-,24-,33+,34-/m0/s1

2.1.3 InChI Key

FIGNGSHKNAHTSH-JJMFXPFOSA-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)CO)O)N)OCC6=CC=CC=C6

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)CO)O)N)OCC6=CC=CC=C6

2.2 Other Identifiers

2.2.1 UNII

6QPN83HK2M

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 677017-23-1

2. Wp 769

3. Berubicin [inn]

4. 6qpn83hk2m

5. (7s,9s)-7-[(2r,4s,5s,6s)-4-amino-6-methyl-5-phenylmethoxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione

6. Unii-6qpn83hk2m

7. Wp-769

8. Berubicin [who-dd]

9. Chembl2110580

10. Dtxsid70217986

11. Zinc72267022

12. Bb178714

13. Q27265347

14. (8s,10s)-10-((3-amino-4-o-benzyl-2,3,6-trideoxy-a-l-lyxo-hexopyranosyl)oxy)-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione

15. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-4-o-(phenylmethyl)-.alpha.-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8s,10s)-

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₃₄H₃₅NO₁₁
Molecular Weight	633.6 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	8
Exact Mass	633.22101093 g/mol
Monoisotopic Mass	633.22101093 g/mol
Topological Polar Surface Area	195 Å²
Heavy Atom Count	46
Formal Charge	0
Complexity	1130
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	1