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Geldanamycin

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ACTIVE PHARMA INGREDIENTS

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Synopsis

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Chemistry

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Also known as: 30562-34-6, Chebi:5292, Nsc-122750, Z3k3vj16ku, U-29135, Mfcd00274570

Molecular Formula

C₂₉H₄₀N₂O₉

Molecular Weight

560.6 g/mol

InChI Key

QTQAWLPCGQOSGP-KSRBKZBZSA-N

FDA UNII

Z3K3VJ16KU

Geldanamycin is a benzoquinone antineoplastic antibiotic isolated from the bacterium Streptomyces hygroscopicus. Geldanamycin binds to and inhibits the cytosolic chaperone functions of heat shock protein 90 (HSP90). HSP90 maintains the stability and functional shape of many oncogenic signaling proteins; the inhibition of HSP90 promotes the proteasomal degradation of oncogenic signaling proteins that may be over-expressed or overactive in tumor cells. (NCI04)

1 2D Structure

Geldanamycin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate

2.1.2 InChI

InChI=1S/C29H40N2O9/c1-15-11-19-25(34)20(14-21(32)27(19)39-7)31-28(35)16(2)9-8-10-22(37-5)26(40-29(30)36)18(4)13-17(3)24(33)23(12-15)38-6/h8-10,13-15,17,22-24,26,33H,11-12H2,1-7H3,(H2,30,36)(H,31,35)/b10-8-,16-9+,18-13+/t15-,17+,22+,23+,24-,26+/m1/s1

2.1.3 InChI Key

QTQAWLPCGQOSGP-KSRBKZBZSA-N

2.1.4 Canonical SMILES

CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C(=C(C1)C2=O)OC)C)OC)OC(=O)N)C)C)O)OC

2.1.5 Isomeric SMILES

C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(/[C@@H]([C@H](/C=C\C=C(\C(=O)NC2=CC(=O)C(=C(C1)C2=O)OC)/C)OC)OC(=O)N)\C)C)O)OC

2.2 Other Identifiers

2.2.1 UNII

Z3K3VJ16KU

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Geldanomycin

2.3.2 Depositor-Supplied Synonyms

1. 30562-34-6

2. Chebi:5292

3. Nsc-122750

4. Z3k3vj16ku

5. U-29135

6. Mfcd00274570

7. [(3r,5s,6r,7s,8e,10s,11s,12z,14e)-6-hydroxy-5,11,21-trimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] Carbamate

8. Gdm

9. Nsc 122750

10. (4e,6z,8s,9s,10e,12s,13r,14s,16r)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl Carbamate

11. Unii-z3k3vj16ku

12. 1yet

13. [8s-(4e,6z,8r*,9r*,10e,12r*,13s*,14r*,16s*)]-9-[(aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione

14. Geldanamycin (9ci)

15. Brn 1633093

16. Geldanamycin [mi]

17. Schembl4154

18. U 29135

19. Bspbio_001073

20. Gtpl9829

21. Dtxsid7042691

22. Geldanamycin Ready Made Solution

23. Schembl13037476

24. Chebi:91381

25. Hms1362e15

26. Hms1792e15

27. Hms1990e15

28. Hms3403e15

29. Bdbm50008059

30. Ei-280

31. Akos024456552

32. Zinc100064834

33. Ccg-208040

34. Db02424

35. Idi1_002122

36. Ncgc00163449-01

37. Ncgc00163449-02

38. 2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-, 9-carbamate (8ci)

39. Geldanamycin From Streptomyces Hygroscopicus

40. G0334

41. Sr-05000002266

42. A1-50253

43. J-018017

44. J-521410

45. Sr-05000002266-3

46. Brd-k11528507-001-01-8

47. Geldanamycin, Streptomyces Hygroscopicus - Cas 30562-34-6

48. Geldanamycin From Streptomyces Hygroscopicus, >=98% (hplc), Powder

49. [(3s,5s,6r,7s,8e,10r,11s,12z,14e)-6-hydroxy-5,11,21-trimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-8,12,14,18,21-pentaen-10-yl] Carbamate

50. [(4e,6z,8s,9s,10e,12s,13r,14s,16r)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] Carbamate

51. 2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9-[(aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-, (4e,6z,8s,9s,10e,12s,13r,14s,16r)-

52. 2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9-[(aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-, [8s-(4e,6z,8r*,9r*,10e,12r*,13s*,14r*,16s*)]-

53. Gmy

2.4 Create Date

2005-06-01

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₄₀N₂O₉
Molecular Weight	560.6 g/mol
XLogP3	2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	5
Exact Mass	560.27338086 g/mol
Monoisotopic Mass	560.27338086 g/mol
Topological Polar Surface Area	164 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	1150
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	3
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

Cysteine Proteinase Inhibitors

Exogenous and endogenous compounds which inhibit CYSTEINE ENDOPEPTIDASES. (See all compounds classified as Cysteine Proteinase Inhibitors.)

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

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