Payload Information

General Information of This Payload
Payload ID
PAY0DWOSZ
Name
Tiancimycin
Synonyms
Tiancimycin; CHEMBL4636420; SCHEMBL17918234
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Target(s) Microtubule (MT)
 Target Info 
Structure
Formula
C27H19NO8
Isosmiles
C[C@H]([C@]12[C@@H]3C#C/C=C\C#C[C@H]([C@@]1(O2)C4=CC(=C5C(=C4N3)C(=O)C6=C(C5=O)C=CC(=C6O)OC)O)O)O
PubChem CID
121477750
InChI
InChI=1S/C27H19NO8/c1-12(29)26-17-7-5-3-4-6-8-18(31)27(26,36-26)14-11-15(30)20-21(22(14)28-17)25(34)19-13(23(20)32)9-10-16(35-2)24(19)33/h3-4,9-12,17-18,28-31,33H,1-2H3/b4-3-/t12-,17+,18-,26+,27+/m1/s1
InChIKey
DJOMZYYFFHCVSQ-UBZKRVARSA-N
IUPAC Name
(1S,17S,20Z,24R,26R)-4,11,24-trihydroxy-26-[(1R)-1-hydroxyethyl]-10-methoxy-25-oxa-16-azahexacyclo[15.7.2.01,26.02,15.05,14.07,12]hexacosa-2,4,7(12),8,10,14,20-heptaen-18,22-diyne-6,13-dione
Pharmaceutical Properties
Molecule Weight
485.4
Polar area
149
Complexity
1170
xlogp Value
2.3
Heavy Count
36
Rot Bonds
2
Hbond acc
9
Hbond Donor
5
The activity data of This Payload
Standard Type Value Units Cell line Disease Model Cell line ID Reference
Half Maximal Effective Concentration (EC50) 0.45 nM
SF-295 cells
Glioblastoma
CVCL_1690 
[1]
Half Maximal Effective Concentration (EC50) 0.74 nM
SK-MEL-5 cells
Cutaneous melanoma
CVCL_0527 
[1]
Half Maximal Effective Concentration (EC50) 1.1 nM
MDA-MB-231 cells (5T4 overexpression)
Breast adenocarcinoma
CVCL_0062 
[1]
Half Maximal Effective Concentration (EC50) 4.2 nM
NCI-H226 cells
Pleural epithelioid mesothelioma
CVCL_1544 
[1]
Half Maximal Inhibitory Concentration (IC50) 400 nM
LT12 tumor cells
Rat leukemia
CVCL_D271 
[2]
Each Antibody-drug Conjugate Related to This Payload
References
Ref 1 Characterization of TnmH as an O-Methyltransferase Revealing Insights into Tiancimycin Biosynthesis and Enabling a Biocatalytic Strategy To Prepare Antibody-Tiancimycin Conjugates. J Med Chem. 2020 Aug 13;63(15):8432-8441. doi: 10.1021/acs.jmedchem.0c00799. Epub 2020 Jul 24.
Ref 2 Synthesis, antiproliferative activity and inhibition of tubulin polymerization by 1,5- and 1,8-disubstituted 10H-anthracen-9-ones bearing a 10-benzylidene or 10-(2-oxo-2-phenylethylidene) moiety. Eur J Med Chem. 2010 Aug;45(8):3420-38. doi: 10.1016/j.ejmech.2010.04.032.

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