General Information of the Compound
Compound ID
CP0054776
Compound Name
BMS-722782
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Synonyms
17AAG, Tanespimycin, Geldanamycin, NSC330507, 17-(Allylamino)-17-demethoxygeldanamycin, CP 127374
CNF-101
Tanespimycin
[(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-6-hydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-21-(prop-2-enylamino)-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate
[(3S,5S,6R,7S,8E,10R,11S,12E,14E)-6-Hydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-21-(prop-2-enylamino)-17-azabicyclo[16.3.1]docosa-8,12,14,18,21-pentaen-10-yl] carbamate
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Structure
Formula
C31H43N3O8
Molecular Weight
585.698
Canonical SMILES
CO[C@H]1C[C@H](C)CC2=C(NCC=C)C(=O)C=C(NC(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@H]1O)C2=O
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InChI
InChI=1S/C31H43N3O8/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9-,18-10+,20-15+/t17-,19+,24+,25+,27-,29+/m1/s1
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InChIKey
AYUNIORJHRXIBJ-TXHRRWQRSA-N
CAS
75747-14-7
Physicochemical Property
logP
2.5376
Rotatable Bonds
6
Heavy Atom Count
42
Polar Areas
166.28
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
9
Complexity
42

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 6505803
SID: 14862440
ChEMBL ID
CHEMBL109480
DrugBank ID
DB05134
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT01500, Heat shock protein HSP 90-alpha
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000083 MCF-7
 Cell Line Info 
Homo sapiens (Human)  1
1
EC50 = 12 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 EC50 = 64.9 nM
2 EC50 = 1000 nM
3 GI50 = 32 nM
4 IC50 = 20 nM
5 IC50 = 46 nM
6 IC50 = 56 nM
7 IC50 = 140 nM
8 IC50 = 309 nM
9 IC50 = 780 nM
10 IC50 = 1190 nM
11 IC50 = 1270 nM
12 IC50 = 9800 nM
13 Kd = 160 nM
14 Kd = 220 nM
15 Kd = 310 nM
16 Kd = 326 nM
17 Kd = 388 nM
18 Kd = 760 nM
19 Ki = 4.6 nM
20 Ki = 29 nM
Protein ID: PT01478, Heat shock protein HSP 90-beta
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000083 MCF-7
 Cell Line Info 
Homo sapiens (Human)  1
1
IC50 = 12 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 Activity = 1270 nM
2 EC50 = 1000 nM
3 IC50 = 7 nM
4 IC50 = 45 nM
5 IC50 = 1270 nM
6 Kd = 7.3 nM
7 Kd = 1300 nM
8 Ki = 9 nM
9 Ki = 530 nM
Cell Viability or Cytotoxicity Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000261 SK-BR-3
 Cell Line Info 
Homo sapiens (Human)  1
1
EC50 = 25 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( Tanespimycin )
Drug Name Tanespimycin
Company Bristol-Myers Squibb; Infinity Pharmaceuticals
Indication
Breast cancer
Phase 2
Multiple myeloma
Discontinued in Phase 3
Target(s)
Heat shock protein 90 alpha (HSP90A)
 Target Info 
Inhibitor