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2D Structure
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

2D Structure

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 Weight 633.6 g/mol
Molecular Formula C34H35NO11
XLogP33.3
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count12
Rotatable Bond Count8
Exact Mass633.22101093 g/mol
Monoisotopic Mass633.22101093 g/mol
Topological Polar Surface Area195 Ų
Heavy Atom Count46
Formal Charge0
Complexity1130
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1