Payload Information

General Information of This Payload
Payload ID
PAY0YEFWC
Name
Duocarmycin Sa
Synonyms
Duocarmycin sa; 130288-24-3; (+)-duocarmycin SA; Antibiotic DC113; methyl (1R,12S)-7-oxo-10-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-5,10-diazatetracyclo[7.4.0.01,12.02,6]trideca-2(6),3,8-triene-4-carboxylate; C25H23N3O7; Cyclopropa(c)pyrrolo(3,2-e)indole-6-carboxylic acid, 1,2,4,5,8,8a-hexahydro-4-oxo-2-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester, (7bR)-; duocarmycinsa; Cyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylic acid, 1,2,4,5,8,8a-hexahydro-4-oxo-2-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-, methyl ester, (7bR)-; SCHEMBL61916; CHEMBL308086; DTXSID30926663; C25-H23-N3-O7; HY-12456; LS-63651; CS-0011400
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Target(s) Human Deoxyribonucleic acid (hDNA)
 Target Info 
Structure
Formula
C25H23N3O7
Isosmiles
COC1=C(C(=C2C(=C1)C=C(N2)C(=O)N3C[C@H]4C[C@@]45C3=CC(=O)C6=C5C=C(N6)C(=O)OC)OC)OC
PubChem CID
115369
InChI
InChI=1S/C25H23N3O7/c1-32-17-6-11-5-14(26-19(11)22(34-3)21(17)33-2)23(30)28-10-12-9-25(12)13-7-15(24(31)35-4)27-20(13)16(29)8-18(25)28/h5-8,12,26-27H,9-10H2,1-4H3/t12-,25-/m1/s1
InChIKey
VQNATVDKACXKTF-XELLLNAOSA-N
IUPAC Name
methyl (1R,12S)-7-oxo-10-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-5,10-diazatetracyclo[7.4.0.01,12.02,6]trideca-2(6),3,8-triene-4-carboxylate
Pharmaceutical Properties
Molecule Weight
477.5
Polar area
123
Complexity
971
xlogp Value
2.6
Heavy Count
35
Rot Bonds
6
Hbond acc
7
Hbond Donor
2
The activity data of This Payload
Standard Type Value Units Cell line Disease Model Cell line ID Reference
Half Maximal Inhibitory Concentration (IC50) 0.0018 nM
U-138MG cells
Astrocytoma
CVCL_0020 
[1]
Half Maximal Inhibitory Concentration (IC50) 0.006 nM
L1210 cells
Lymphoblastic leukemia
CVCL_0382 
[2]
Half Maximal Inhibitory Concentration (IC50) 0.01 nM
L1210 cells
Lymphoblastic leukemia
CVCL_0382 
Half Maximal Inhibitory Concentration (IC50) 0.01 nM
L1210 cells
Lymphoblastic leukemia
CVCL_0382 
[3]
Half Maximal Inhibitory Concentration (IC50) 0.01 nM
L1210 cells
Lymphoblastic leukemia
CVCL_0382 
[4]
Half Maximal Inhibitory Concentration (IC50) 0.01 nM
L1210 cells
Lymphoblastic leukemia
CVCL_0382 
[5]
Half Maximal Inhibitory Concentration (IC50) 0.01 nM
L1210 cells
Lymphoblastic leukemia
CVCL_0382 
[6]
Half Maximal Inhibitory Concentration (IC50) 0.1 nM
L1210 cells
Lymphoblastic leukemia
CVCL_0382 
Half Maximal Inhibitory Concentration (IC50) 0.4 nM
U-138MG cells
Astrocytoma
CVCL_0020 
[1]
Half Maximal Inhibitory Concentration (IC50) 0.443 nM
U-138MG cells
Astrocytoma
CVCL_0020 
[1]
Half Maximal Inhibitory Concentration (IC50) 22.3 nM
LNCaP cells
Prostate carcinoma
CVCL_0395 
[7]
Each Antibody-drug Conjugate Related to This Payload
References
Ref 1 Duocarmycin SA, a potent antitumor antibiotic, sensitizes glioblastoma cells to proton radiation. Bioorg Med Chem Lett. 2018 Sep 1;28(16):2688-2692. doi: 10.1016/j.bmcl.2018.04.008. Epub 2018 Apr 4.
Ref 2 Synthesis and evaluation of a series of C5'-substituted duocarmycin SA analogs. Bioorg Med Chem Lett. 2010 May 1;20(9):2722-5. doi: 10.1016/j.bmcl.2010.03.078. Epub 2010 Mar 25.
Ref 3 Bifunctional alkylating agents derived from duocarmycin SA: potent antitumor activity with altered sequence selectivity. Bioorg Med Chem Lett. 2000 Mar 6;10(5):495-8. doi: 10.1016/s0960-894x(00)00042-1.
Ref 4 Fundamental relationships between structure, reactivity, and biological activity for the duocarmycins and CC-1065. J Med Chem. 2009 Oct 8;52(19):5771-80. doi: 10.1021/jm9006214.
Ref 5 A novel, unusually efficacious duocarmycin carbamate prodrug that releases no residual byproduct. J Med Chem. 2012 Jun 28;55(12):5878-86. doi: 10.1021/jm300330b. Epub 2012 Jun 12.
Ref 6 Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]imidazolo[4,5-e]indol-4-one-6-carboxylate (CImI) alkylation subunit. Bioorg Med Chem. 2016 Oct 15;24(20):4779-4786. doi: 10.1016/j.bmc.2016.04.050. Epub 2016 Apr 26.
Ref 7 Synthesis and biological analysis of prostate-specific membrane antigen-targeted anticancer prodrugs. J Med Chem. 2010 Nov 11;53(21):7767-77. doi: 10.1021/jm100729b.

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