Payload Information

General Information of This Payload
Payload ID
PAY0OWBST
Name
Puromycin
Synonyms
Puromycin; 53-79-2; Stylomycin; Puromycine; Puromicina; Puromycinum; P-638; 3123L; Puromycin dihydrochloride; CHEBI:17939; GNF-PF-2016; CL 13,900; Stillomycin; CL 13900; CL-13900; Puromycine [INN-French]; Puromycinum [INN-Latin]; Puromicina [INN-Spanish]; UNII-4A6ZS6Q2CL; 4A6ZS6Q2CL; 3'-(L-alpha-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine; Puromycin [USAN:INN:BAN]; (S)-3'-((2-Amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-deoxy-N,N-dimethyladenosine; P 638; Puromycin (USAN); PUROMYCIN [USAN]; NSC 3055; 3123-L; 9-{3-deoxy-3-[(O-methyl-L-tyrosyl)amino]-beta-D-xylofuranosyl}-N,N-dimethyl-9H-purin-6-amine; Adenosine, 3'-(((2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-deoxy-N,N-dimethyl-; (S)-2-amino-N-((2S,3S,4R,5R)-5-(6-(dimethylamino)-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl)-3-(4-methoxyphenyl)propanamide; Achromycin (purine derivative); TCMDC-123493; 3'-deoxy-N,N-dimethyl-3'-(O-methyl-L-tyrosinamido)adenosine; C22H29N7O5; 3'-[[(2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3'-deoxy-N,N-diemthyladenosine; 6-Dimethylamino-9-(3'-(p-methoxy-L-phenylalanylamino)-beta-D-ribofuranosyl)-purine; CL 16536; NSC3055; NSC-3055; Adenosine, 3'-((2-amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-deoxy-N,N-dimethyl-, (S)-; 58-58-2; 3'-deoxy-N,N-dimethyl-3'-[(O-methyl-L-tyrosyl)amino]adenosine; (S)-3'-[[2-Amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3'-deoxy-N,N-dimethyladenosine; Adenosine, 3'-[[(2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3'-deoxy-N,N-dimethyl-; PUY; PUROMYCIN [INN]; PUROMYCIN [MI]; Prestwick3_000480; Epitope ID:140945; PUROMYCIN [WHO-DD]; SCHEMBL4570; BSPBio_000620; Puromycin [USAN:BAN:INN]; BPBio1_000682; CHEMBL469912; DTXSID8036788; 3'-(L-.alpha.-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine; Adenosine, 3'-(alpha-amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyl-, L-; RXWNCPJZOCPEPQ-NVWDDTSBSA-N; HMS2089F18; HY-B1743; CL 16,536 (*Dihydrochloride*); BDBM50277158; MFCD00866328; AKOS030485964; C22-H29-N7-O5; CCG-208505; CS-6500; DB08437; Puromycin, 10 mg/ml in distilled water; NCGC00179500-01; NCGC00179500-07; NCGC00179500-14; (2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide; AB00514661; C01610; D05653; AB00514661-07; Q424696; BRD-K36007650-001-01-9; BRD-K36007650-300-02-3; Q27167243; L-3'-(alpha-amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine; (2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl]-3-(4-methoxyphenyl)propanamide; 2-amino-N-[5-[6-(dimethylamino)-9-purinyl]-4-hydroxy-2-(hydroxymethyl)-3-oxolanyl]-3-(4-methoxyphenyl)propanamide; Adenosine, 3'-(-amino-p-methoxyhydrocinnamamido)-3'-deoxy-N, N-dimethyl-, dihydrochloride, L-
   Click to Show/Hide
Target(s) Ribosome (RB)
 Target Info 
Structure
Formula
C22H29N7O5
Isosmiles
CN(C)C1=NC=NC2=C1N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)NC(=O)[C@H](CC4=CC=C(C=C4)OC)N)O
PubChem CID
439530
InChI
InChI=1S/C22H29N7O5/c1-28(2)19-17-20(25-10-24-19)29(11-26-17)22-18(31)16(15(9-30)34-22)27-21(32)14(23)8-12-4-6-13(33-3)7-5-12/h4-7,10-11,14-16,18,22,30-31H,8-9,23H2,1-3H3,(H,27,32)/t14-,15+,16+,18+,22+/m0/s1
InChIKey
RXWNCPJZOCPEPQ-NVWDDTSBSA-N
IUPAC Name
(2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide
Pharmaceutical Properties
Molecule Weight
471.5
Polar area
161
Complexity
680
xlogp Value
0
Heavy Count
34
Rot Bonds
8
Hbond acc
10
Hbond Donor
4
The activity data of This Payload
Standard Type Value Units Cell line Disease Model Cell line ID Reference
Half Maximal Inhibitory Concentration (IC50) 0.5 ug/mL
P388 cells
Lymphoma
CVCL_7222 
[1]
Half Maximal Inhibitory Concentration (IC50) 0.35 nM
HEK293 cells
Normal
CVCL_0045 
[2]
Half Maximal Inhibitory Concentration (IC50) 10000 nM
J774.A1 cells
Mouse reticulum cell sarcoma
CVCL_0358 
[3]
Half Maximal Effective Concentration (EC50) 170 nM
MOLT-4 cells
Adult T acute lymphoblastic leukemia
CVCL_0013 
[4]
Half Maximal Inhibitory Concentration (IC50) 20200 nM
HepG2/Adm cells
Hepatoblastoma
CVCL_M187 
[5]
Half Maximal Inhibitory Concentration (IC50) 210 nM
Hep-G2 cells
Hepatoblastoma
CVCL_0027 
[5]
Half Maximal Inhibitory Concentration (IC50) 210 nM
KB 3-1 cells
Cervical epithelial carcinoma
CVCL_2088 
[6]
Half Maximal Inhibitory Concentration (IC50) 220 nM
K-562 cells
Chronic myelogenous leukemia
CVCL_0004 
[6]
Half Maximal Inhibitory Concentration (IC50) 230 nM
Hep-G2 cells
Hepatoblastoma
CVCL_0027 
[6]
Half Maximal Inhibitory Concentration (IC50) 26830 nM
K-562 cells
Chronic myelogenous leukemia
CVCL_0004 
[6]
Half Maximal Inhibitory Concentration (IC50) 300 nM
A-549 cells
Lung adenocarcinoma
CVCL_0023 
[7]
Half Maximal Inhibitory Concentration (IC50) 300 nM
PC-3 cells
Prostate carcinoma
CVCL_0035 
[7]
Half Maximal Inhibitory Concentration (IC50) 350.5 nM
HEK293 cells
Normal
CVCL_0045 
[8]
Half Maximal Inhibitory Concentration (IC50) 360 nM
HEK293 cells
Normal
CVCL_0045 
[9]
Half Maximal Inhibitory Concentration (IC50) 360 nM
HEK293 cells
Normal
CVCL_0045 
[10]
Half Maximal Inhibitory Concentration (IC50) 361 nM
HEK293 cells
Normal
CVCL_0045 
[11]
Half Maximal Inhibitory Concentration (IC50) 399 nM
HEK293 cells
Normal
CVCL_0045 
[12]
Half Maximal Inhibitory Concentration (IC50) 400 nM
HEK293 cells
Normal
CVCL_0045 
[13]
Half Maximal Inhibitory Concentration (IC50) 420 nM
HEK293 cells
Normal
CVCL_0045 
[14]
Half Maximal Inhibitory Concentration (IC50) 450 nM
HEK293 cells
Normal
CVCL_0045 
[15]
Half Maximal Inhibitory Concentration (IC50) 460 nM
HEK293 cells
Normal
CVCL_0045 
[16]
Half Maximal Inhibitory Concentration (IC50) 460 nM
HEK293 cells
Normal
CVCL_0045 
[17]
Half Maximal Inhibitory Concentration (IC50) 5 nM
WI-38 VA13 cells
Normal
CVCL_2759 
[18]
Half Maximal Effective Concentration (EC50) 55 nM
HL-60 cells
Adult acute myeloid leukemia
CVCL_0002 
[4]
Half Maximal Inhibitory Concentration (IC50) 600 nM
A-549 cells
Lung adenocarcinoma
CVCL_0023 
[19]
Half Maximal Effective Concentration (EC50) 6100 nM
HCT-8 cells
Ileocecal adenocarcinoma
CVCL_2478 
[20]
Half Maximal Inhibitory Concentration (IC50) 694 nM
HEK293 cells
Normal
CVCL_0045 
[21]
Half Maximal Inhibitory Concentration (IC50) 700 nM
PC-3 cells
Prostate carcinoma
CVCL_0035 
[19]
Half Maximal Inhibitory Concentration (IC50) 79300 nM
KB-V1 cells
Cervical carcinoma
CVCL_2089 
[6]
Half Maximal Inhibitory Concentration (IC50) 810 nM
HEK293 cells
Normal
CVCL_0045 
[22]
Half Maximal Inhibitory Concentration (IC50) 83930 nM
Hep-G2 cells
Hepatoblastoma
CVCL_0027 
[6]
Each Antibody-drug Conjugate Related to This Payload
Full Information of The Activity Data of The ADC(s) Related to This Payload
Cetuximab-Puromycin [Investigative]
 ADC Info 
Revealed Based on the Cell Line Data
Click To Hide/Show 1 Activity Data Related to This Level
Experiment 1 Reporting the Activity Date of This ADC [23]
Efficacy Data Half Maximal Inhibitory Concentration (IC50)
37.42 ug/mL
High EGFR expression (EGFR+++)
Method Description
Cells were seeded into 6-well plates, 500,000 cells/well. One day (24 hours) before treatment, MDA-MB-231 cells are being fasted from FBS. Cells are divided into five different doses of conjugate (5 ug/mL; 10 ug/mL; 20 ug/mL; 40 ug/mL; 80 ug/mL) and one untreated group. They were incubated for 48 hours.
In Vitro Model Breast adenocarcinoma MDA-MB-468 cells CVCL_0419
References
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Ref 4 Puromycin based inhibitors of aminopeptidases for the potential treatment of hematologic malignancies. Eur J Med Chem. 2017 Oct 20;139:325-336. doi: 10.1016/j.ejmech.2017.07.048. Epub 2017 Jul 26.
Ref 5 Tenacigenin B derivatives reverse P-glycoprotein-mediated multidrug resistance inHepG2/Dox cells. J Nat Prod. 2008 Jun;71(6):1049-51. doi: 10.1021/np070458f. Epub 2008 May 31.
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Ref 7 Puromycins B-E, Naturally Occurring Amino-Nucleosides Produced by the Himalayan Isolate Streptomyces sp. PU-14G. J Nat Prod. 2018 Nov 26;81(11):2560-2566. doi: 10.1021/acs.jnatprod.8b00720. Epub 2018 Nov 12.
Ref 8 An evaluation of Minor Groove Binders as anti-Trypanosoma brucei brucei therapeutics. Eur J Med Chem. 2016 Jun 30;116:116-125. doi: 10.1016/j.ejmech.2016.03.064. Epub 2016 Mar 29.
Ref 9 Polyoxygenated Cyclohexenes and Other Constituents of Cleistochlamys kirkii Leaves. J Nat Prod. 2017 Jan 27;80(1):114-125. doi: 10.1021/acs.jnatprod.6b00759. Epub 2016 Dec 21.
Ref 10 A Meroisoprenoid, Heptenolides, and C-Benzylated Flavonoids from Sphaerocoryne gracilis ssp. gracilis. J Nat Prod. 2020 Feb 28;83(2):316-322. doi: 10.1021/acs.jnatprod.9b00721. Epub 2020 Feb 18.
Ref 11 Rotenoids, Flavonoids, and Chalcones from the Root Bark of Millettia usaramensis. J Nat Prod. 2015 Dec 24;78(12):2932-9. doi: 10.1021/acs.jnatprod.5b00581. Epub 2015 Dec 14.
Ref 12 Antiplasmodial -triketones from the flowers of the Australian tree Angophora woodsiana. Bioorg Med Chem Lett. 2017 Jun 1;27(11):2602-2607. doi: 10.1016/j.bmcl.2017.03.065. Epub 2017 Mar 24.
Ref 13 Antiplasmodial -Triketone-Flavanone Hybrids from the Flowers of the Australian Tree Corymbia torelliana. J Nat Prod. 2018 Jul 27;81(7):1588-1597. doi: 10.1021/acs.jnatprod.8b00154. Epub 2018 Jul 3.
Ref 14 7',8'-Dihydroobolactone, a typanocidal alpha-pyrone from the rainforest tree Cryptocarya obovata. Bioorg Med Chem Lett. 2010 Jul 15;20(14):4057-9. doi: 10.1016/j.bmcl.2010.05.091. Epub 2010 May 25.
Ref 15 Pimentelamines A-C, Indole Alkaloids Isolated from the Leaves of the Australian Tree Flindersia pimenteliana. J Nat Prod. 2017 Dec 22;80(12):3211-3217. doi: 10.1021/acs.jnatprod.7b00587. Epub 2017 Dec 13.
Ref 16 Synthesis of antimalarial amide analogues based on the plant serrulatane diterpenoid 3,7,8-trihydroxyserrulat-14-en-19-oic acid. Bioorg Med Chem Lett. 2017 Sep 1;27(17):4091-4095. doi: 10.1016/j.bmcl.2017.07.039. Epub 2017 Jul 15.
Ref 17 Microthecaline A, a Quinoline Serrulatane Alkaloid from the Roots of the Australian Desert Plant Eremophila microtheca. J Nat Prod. 2018 Apr 27;81(4):1079-1083. doi: 10.1021/acs.jnatprod.7b00992. Epub 2018 Mar 13.
Ref 18 Bioactive guaianolides from siyekucai (Ixeris chinensis). J Nat Prod. 2006 Oct;69(10):1425-8. doi: 10.1021/np068015j.
Ref 19 Design, synthesis and biological evaluation of diaziridinyl quinone isoxazole hybrids. Eur J Med Chem. 2016 Jul 19;117:85-98. doi: 10.1016/j.ejmech.2016.03.042. Epub 2016 Apr 6.
Ref 20 Herbicidins from Streptomyces sp. CB01388 Showing Anti- Cryptosporidium Activity. J Nat Prod. 2018 Apr 27;81(4):791-797. doi: 10.1021/acs.jnatprod.7b00850. Epub 2018 Feb 22.
Ref 21 Acrotrione: An Oxidized Xanthene from the Roots of Acronychia pubescens. J Nat Prod. 2019 Apr 26;82(4):1019-1023. doi: 10.1021/acs.jnatprod.8b00956. Epub 2019 Mar 13.
Ref 22 Antiplasmodial Alkaloids from the Australian Bryozoan Amathia lamourouxi. J Nat Prod. 2020 Nov 25;83(11):3435-3444. doi: 10.1021/acs.jnatprod.0c00929. Epub 2020 Oct 26.
Ref 23 Conjugation of Cetuximab - Puromycin and Its Target-Specific Effect on Triple Negative Breast Cancer Cell Lines. Asian Pac J Cancer Prev. 2022 May 1;23(5):1803-1812.

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