Payload Information

General Information of This Payload
Payload ID
PAY0CZRPM
Name
Auristatin E
Synonyms
Auristatin E; 160800-57-7; (2S)-2-[[(2S)-2-(dimethylamino)-3-methylbutanoyl]amino]-N-[(3R,4S,5S)-1-[(2S)-2-[(1R,2R)-3-[[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino]-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl]-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N,3-dimethylbutanamide; (S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N-((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)-N,3-dimethylbutanamide; SCHEMBL1687439; CHEMBL4082989; WOWDZACBATWTAU-FEFUEGSOSA-N; AMY10330; EX-A3360; AKOS040741181; CS-3435; BP-23645; HY-15582; MS-31271; F85071
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Target(s) Microtubule (MT)
 Target Info 
Structure
Formula
C40H69N5O7
Isosmiles
CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@@H]([C@@H](C)C(=O)N[C@H](C)[C@H](C2=CC=CC=C2)O)OC)OC)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)N(C)C
PubChem CID
11498622
InChI
InChI=1S/C40H69N5O7/c1-14-26(6)35(44(11)40(50)33(24(2)3)42-39(49)34(25(4)5)43(9)10)31(51-12)23-32(46)45-22-18-21-30(45)37(52-13)27(7)38(48)41-28(8)36(47)29-19-16-15-17-20-29/h15-17,19-20,24-28,30-31,33-37,47H,14,18,21-23H2,1-13H3,(H,41,48)(H,42,49)/t26-,27+,28+,30-,31+,33-,34-,35-,36+,37+/m0/s1
InChIKey
WOWDZACBATWTAU-FEFUEGSOSA-N
IUPAC Name
(2S)-2-[[(2S)-2-(dimethylamino)-3-methylbutanoyl]amino]-N-[(3R,4S,5S)-1-[(2S)-2-[(1R,2R)-3-[[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino]-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl]-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N,3-dimethylbutanamide
Pharmaceutical Properties
Molecule Weight
732
Polar area
141
Complexity
1130
xlogp Value
4.5
Heavy Count
52
Rot Bonds
20
Hbond acc
8
Hbond Donor
3
The activity data of This Payload
Standard Type Value Units Cell line Disease Model Cell line ID Reference
Half Maximal Cell Growth Inhibitory Concentration (GI50) 0.232 nM
MCF7-F (fulvestrant resistant) cells
Invasive breast carcinoma
CVCL_0031 
[1]
Half Maximal Cell Growth Inhibitory Concentration (GI50) 0.232 nM
MCF7-F (fulvestrant resistant) cells
Invasive breast carcinoma
CVCL_0031 
[2]
Half Maximal Cell Growth Inhibitory Concentration (GI50) 0.232 nM
MCF7-F (fulvestrant resistant) cells
Invasive breast carcinoma
CVCL_0031 
[3]
Half Maximal Cell Growth Inhibitory Concentration (GI50) 0.424 nM
DU145 cells
Prostate carcinoma
CVCL_0105 
[1]
Half Maximal Cell Growth Inhibitory Concentration (GI50) 0.424 nM
DU145 cells
Prostate carcinoma
CVCL_0105 
[2]
Half Maximal Cell Growth Inhibitory Concentration (GI50) 0.424 nM
DU145 cells
Prostate carcinoma
CVCL_0105 
[3]
Half Maximal Cell Growth Inhibitory Concentration (GI50) 0.492 nM
SF268 cells
Astrocytoma
CVCL_1689 
[1]
Half Maximal Cell Growth Inhibitory Concentration (GI50) 0.492 nM
SF268 cells
Astrocytoma
CVCL_1689 
[2]
Half Maximal Cell Growth Inhibitory Concentration (GI50) 0.492 nM
SF268 cells
Astrocytoma
CVCL_1689 
[3]
Half Maximal Cell Growth Inhibitory Concentration (GI50) 0.492 nM
KM-20L2 cells
Colon carcinoma
CVCL_D889 
[1]
Half Maximal Cell Growth Inhibitory Concentration (GI50) 0.492 nM
KM-20L2 cells
Colon carcinoma
CVCL_D889 
[2]
Half Maximal Cell Growth Inhibitory Concentration (GI50) 0.492 nM
KM-20L2 cells
Colon carcinoma
CVCL_D889 
[3]
Half Maximal Cell Growth Inhibitory Concentration (GI50) 0.533 nM
NCI-H460 cells
Lung large cell carcinoma
CVCL_0459 
[1]
Half Maximal Cell Growth Inhibitory Concentration (GI50) 0.533 nM
NCI-H460 cells
Lung large cell carcinoma
CVCL_0459 
[2]
Half Maximal Cell Growth Inhibitory Concentration (GI50) 0.533 nM
NCI-H460 cells
Lung large cell carcinoma
CVCL_0459 
[3]
Half Maximal Cell Growth Inhibitory Concentration (GI50) >1.37 nM
BxPC-3 CDX model cells
Pancreatic ductal adenocarcinoma
CVCL_0186 
[1]
Half Maximal Cell Growth Inhibitory Concentration (GI50) >1.37 nM
BxPC-3 CDX model cells
Pancreatic ductal adenocarcinoma
CVCL_0186 
[2]
Half Maximal Cell Growth Inhibitory Concentration (GI50) >1.37 nM
BxPC-3 CDX model cells
Pancreatic ductal adenocarcinoma
CVCL_0186 
[3]
Half Maximal Inhibitory Concentration (IC50) 10 nM
A-549 cells
Lung adenocarcinoma
CVCL_0023 
[4]
Each Antibody-drug Conjugate Related to This Payload
References
Ref 1 Antineoplastic Agents. 603. Quinstatins: Exceptional Cancer Cell Growth Inhibitors. J Nat Prod. 2017 Mar 24;80(3):692-698. doi: 10.1021/acs.jnatprod.6b01006. Epub 2017 Feb 17.
Ref 2 Antineoplastic Agents. 604. The Path of Quinstatin Derivatives to Antibody Drug Conjugates. J Nat Prod. 2017 Sep 22;80(9):2447-2452. doi: 10.1021/acs.jnatprod.7b00237. Epub 2017 Sep 12.
Ref 3 Antineoplastic Agents. 605. Isoquinstatins. J Nat Prod. 2018 Mar 23;81(3):451-457. doi: 10.1021/acs.jnatprod.7b00352. Epub 2017 Sep 19.
Ref 4 Syntheses and antitumor activities of N'1,N'3-dialkyl-N'1,N'3-di-(alkylcarbonothioyl) malonohydrazide: the discovery of elesclomol. Bioorg Med Chem Lett. 2013 Sep 15;23(18):5070-6. doi: 10.1016/j.bmcl.2013.07.032. Epub 2013 Jul 25.

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