1-Isothiocyanato-4-methanesulfinyl-butane

ID: ALA48802

Chembl Id: CHEMBL48802

Cas Number: 4478-93-7

PubChem CID: 5350

Product Number: S59765

Max Phase: Phase

Molecular Formula: C6H11NOS2

Molecular Weight: 177.29

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: (-)-sulforaphane | (r)-sulforaphane | 4-(Methylsulfinyl)Butyl Isothiocyanate | Sulforaphane | Sulforaphane, (r)- | sulforaphane|4478-93-7|DL-Sulforaphane|1-Isothiocyanato-4-(methylsulfinyl)butane|D,L-Sulforaphane|Sulforafan|1-Isothiocyanato-4-(methylsulfinyl)-butane|1-isothiocyanato-4-methylsulfinylbutane|Butane, 1-isothiocyanato-4-(methylsulfinyl)-|4-Methylsulfinylbutyl isothiocyanate|(+/-)-sulforaphane|CHEBI:47807|41684WL1GL|Butane, 1-isothiocyanato-4-[(S)-methylsulfinyl]-|4-(Methylsulfinyl)BuShow More

Canonical SMILES:  C[S+]([O-])CCCCN=C=S

Standard InChI:  InChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3

Standard InChI Key:  SUVMJBTUFCVSAD-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

    ALA48802

    SULFORAPHANE

Associated Targets(Human)

HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Jurkat (10389 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-3 (62116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PANC-1 (6144 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NQO1 Tchem Quinone reductase 1 (1746 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NFE2L2 Tchem Nuclear factor erythroid 2-related factor 2 (95332 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Homo sapiens (32628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TP53 Tchem Cellular tumor antigen p53 (48468 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Caco-2 (12174 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PNT1A (47 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOB Tclin Monoamine oxidase B (8835 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOA Tclin Monoamine oxidase A (11911 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KEAP1 Tclin Kelch-like ECH-associated protein 1 (1736 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MIF Tchem Macrophage migration inhibitory factor (979 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NFE2L2 Tchem Keap1/Nrf2 (1722 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTPN11 Tchem Protein-tyrosine phosphatase 2C (2297 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTPN1 Tchem Protein-tyrosine phosphatase 1B (8528 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A-431 (6446 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LoVo (4724 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A-375 (9258 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SMMC-7721 (5516 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAFK Tbio BACH1/MafK (2 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H1299 (3248 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H1975 (4994 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCC827 (1172 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-9 (1037 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hep 3B2 (2332 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SiHa (2051 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCRF-CEM (65223 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U-937 (7138 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ARPE-19 (321 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TGM2 Tchem Protein-glutamine gamma-glutamyltransferase (1221 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U-251 (51189 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HONE1 cell line (118 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H1650 (1118 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H460 (60772 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AGS (1999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SGC-7901 (2773 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SW480 (6023 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-3 (48710 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L02 (4864 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
THP-1 (11052 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Cryz Quinone oxidoreductase (288 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma cruzi (99888 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nqo1 NAD(P)H dehydrogenase [quinone] 1 (1058 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cyp1a1 Cytochrome P450 1A1 (56 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nfe2l2 Nuclear factor erythroid 2-related factor 2 (714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MEF (1005 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDCK (10148 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ahr Aryl hydrocarbon receptor (104 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Abcc2 Canalicular multispecific organic anion transporter 1 (241 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
lasR Transcriptional activator protein lasR (432 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rhlR Regulatory protein RhlR (305 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nfe2l2 KEAP1/NRF2 (98 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nos2 Nitric oxide synthase, inducible (3573 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LLC-PK1 (2135 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Keap1 Kelch-like ECH-associated protein 1 (45 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HBZY-1 (111 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Peritoneal macrophage (1554 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania donovani (89745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania infantum (5912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: YesAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 177.29Molecular Weight (Monoisotopic): 177.0282AlogP: 1.25#Rotatable Bonds: 5
Polar Surface Area: 35.42Molecular Species: NEUTRALHBA: 3HBD:
#RO5 Violations: HBA (Lipinski): 2HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 0.87CX LogP: 0.22CX LogD: 0.22
Aromatic Rings: Heavy Atoms: 10QED Weighted: 0.27Np Likeness Score: 0.73

References

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15. Liang H, Lai B, Yuan Q..  (2008)  Sulforaphane induces cell-cycle arrest and apoptosis in cultured human lung adenocarcinoma LTEP-A2 cells and retards growth of LTEP-A2 xenografts in vivo.,  71  (11): [PMID:18855447] [10.1021/np800233q]
16. Bolognesi ML, Cavalli A, Bergamini C, Fato R, Lenaz G, Rosini M, Bartolini M, Andrisano V, Melchiorre C..  (2009)  Toward a rational design of multitarget-directed antioxidants: merging memoquin and lipoic acid molecular frameworks.,  52  (23): [PMID:19813747] [10.1021/jm901123n]
17. Emmert SW, Desai D, Amin S, Richie JP..  (2010)  Enhanced Nrf2-dependent induction of glutathione in mouse embryonic fibroblasts by isoselenocyanate analog of sulforaphane.,  20  (8): [PMID:20304643] [10.1016/j.bmcl.2010.01.044]
18. Andreani A, Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R, Rambaldi M, Varoli L, Landi L, Prata C, Dalla Sega FV, Caliceti C, Shoemaker RH..  (2010)  Antitumor activity and COMPARE analysis of bis-indole derivatives.,  18  (9): [PMID:20395150] [10.1016/j.bmc.2010.03.063]
19. Avdeef A, Tam KY..  (2010)  How well can the Caco-2/Madin-Darby canine kidney models predict effective human jejunal permeability?,  53  (9): [PMID:20373811] [10.1021/jm901846t]
20. Lee CY, Chew EH, Go ML..  (2010)  Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: synthesis, evaluation and SAR.,  45  (7): [PMID:20392544] [10.1016/j.ejmech.2010.03.023]
21. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]
22. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]
23. Kumar V, Kumar S, Hassan M, Wu H, Thimmulappa RK, Kumar A, Sharma SK, Parmar VS, Biswal S, Malhotra SV..  (2011)  Novel chalcone derivatives as potent Nrf2 activators in mice and human lung epithelial cells.,  54  (12): [PMID:21539383] [10.1021/jm2002348]
24. Conda-Sheridan M, Marler L, Park EJ, Kondratyuk TP, Jermihov K, Mesecar AD, Pezzuto JM, Asolkar RN, Fenical W, Cushman M..  (2010)  Potential chemopreventive agents based on the structure of the lead compound 2-bromo-1-hydroxyphenazine, isolated from Streptomyces species, strain CNS284.,  53  (24): [PMID:21105712] [10.1021/jm1011066]
25. Minarini A, Milelli A, Tumiatti V, Ferruzzi L, Marton MR, Turrini E, Hrelia P, Fimognari C..  (2012)  Design, synthesis and biological evaluation of new naphtalene diimides bearing isothiocyanate functionality.,  48  [PMID:22200402] [10.1016/j.ejmech.2011.12.003]
26. Kachadourian R, Day BJ, Pugazhenti S, Franklin CC, Genoux-Bastide E, Mahaffey G, Gauthier C, Di Pietro A, Boumendjel A..  (2012)  A synthetic chalcone as a potent inducer of glutathione biosynthesis.,  55  (3): [PMID:22239485] [10.1021/jm2016073]
27. Payen L, Courtois A, Loewert M, Guillouzo A, Fardel O..  (2001)  Reactive oxygen species-related induction of multidrug resistance-associated protein 2 expression in primary hepatocytes exposed to sulforaphane.,  282  (1): [PMID:11264000] [10.1006/bbrc.2001.4531]
28. Wang X, Di Pasqua AJ, Govind S, McCracken E, Hong C, Mi L, Mao Y, Wu JY, Tomita Y, Woodrick JC, Fine RL, Chung FL..  (2011)  Selective depletion of mutant p53 by cancer chemopreventive isothiocyanates and their structure-activity relationships.,  54  (3): [PMID:21241062] [10.1021/jm101199t]
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30. Hu K, Qi YJ, Zhao J, Jiang HF, Chen X, Ren J..  (2013)  Synthesis and biological evaluation of sulforaphane derivatives as potential antitumor agents.,  64  [PMID:23685571] [10.1016/j.ejmech.2013.03.045]
31. Xi MY, Jia JM, Sun HP, Sun ZY, Jiang JW, Wang YJ, Zhang MY, Zhu JF, Xu LL, Jiang ZY, Xue X, Ye M, Yang X, Gao Y, Tao L, Guo XK, Xu XL, Guo QL, Zhang XJ, Hu R, You QD..  (2013)  3-aroylmethylene-2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-ones as potent Nrf2/ARE inducers in human cancer cells and AOM-DSS treated mice.,  56  (20): [PMID:24053646] [10.1021/jm400944k]
32. Bonaiuto E, Milelli A, Cozza G, Tumiatti V, Marchetti C, Agostinelli E, Fimognari C, Hrelia P, Minarini A, Di Paolo ML..  (2013)  Novel polyamine analogues: from substrates towards potential inhibitors of monoamine oxidases.,  70  [PMID:24140951] [10.1016/j.ejmech.2013.07.005]
33. Woo SY, Kim JH, Moon MK, Han SH, Yeon SK, Choi JW, Jang BK, Song HJ, Kang YG, Kim JW, Lee J, Kim DJ, Hwang O, Park KD..  (2014)  Discovery of vinyl sulfones as a novel class of neuroprotective agents toward Parkinson's disease therapy.,  57  (4): [PMID:24467268] [10.1021/jm401788m]
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35. Jiang ZY, Lu MC, Xu LL, Yang TT, Xi MY, Xu XL, Guo XK, Zhang XJ, You QD, Sun HP..  (2014)  Discovery of potent Keap1-Nrf2 protein-protein interaction inhibitor based on molecular binding determinants analysis.,  57  (6): [PMID:24512214] [10.1021/jm5000529]
36. Spencer ES, Dale EJ, Gommans AL, Rutledge MT, Vo CT, Nakatani Y, Gamble AB, Smith RA, Wilbanks SM, Hampton MB, Tyndall JD..  (2015)  Multiple binding modes of isothiocyanates that inhibit macrophage migration inhibitory factor.,  93  [PMID:25743213] [10.1016/j.ejmech.2015.02.012]
37. Chen H, Lv L, Soroka D, Warin RF, Parks TA, Hu Y, Zhu Y, Chen X, Sang S..  (2012)  Metabolism of [6]-shogaol in mice and in cancer cells.,  40  (4): [PMID:22246389] [10.1124/dmd.111.043331]
38. Li W, Zheng S, Higgins M, Morra RP, Mendis AT, Chien CW, Ojima I, Mierke DF, Dinkova-Kostova AT, Honda T..  (2015)  New Monocyclic, Bicyclic, and Tricyclic Ethynylcyanodienones as Activators of the Keap1/Nrf2/ARE Pathway and Inhibitors of Inducible Nitric Oxide Synthase.,  58  (11): [PMID:25965897] [10.1021/acs.jmedchem.5b00393]
39. Kim T, Kim YJ, Han IH, Lee D, Ham J, Kang KS, Lee JW..  (2014)  The synthesis of sulforaphane analogues and their protection effect against cisplatin induced cytotoxicity in kidney cells.,  25  (1): [PMID:25466193] [10.1016/j.bmcl.2014.11.014]
40. Lee CY, Yun JH, Kang K, Nho CW, Shin D..  (2015)  Identification of dialkyl diacetylene diols with potent cancer chemopreventive activity.,  25  (18): [PMID:26253633] [10.1016/j.bmcl.2015.05.098]
41. Bertrand HC, Schaap M, Baird L, Georgakopoulos ND, Fowkes A, Thiollier C, Kachi H, Dinkova-Kostova AT, Wells G..  (2015)  Design, Synthesis, and Evaluation of Triazole Derivatives That Induce Nrf2 Dependent Gene Products and Inhibit the Keap1-Nrf2 Protein-Protein Interaction.,  58  (18): [PMID:26348784] [10.1021/acs.jmedchem.5b00602]
42. Lewis SM, Li Y, Catalano MJ, Laciak AR, Singh H, Seiner DR, Reilly TJ, Tanner JJ, Gates KS..  (2015)  Inactivation of protein tyrosine phosphatases by dietary isothiocyanates.,  25  (20): [PMID:26338358] [10.1016/j.bmcl.2015.08.065]
43. Tarozzi A, Marchetti C, Nicolini B, D'Amico M, Ticchi N, Pruccoli L, Tumiatti V, Simoni E, Lodola A, Mor M, Milelli A, Minarini A..  (2016)  Combined inhibition of the EGFR/AKT pathways by a novel conjugate of quinazoline with isothiocyanate.,  117  [PMID:27135370] [10.1016/j.ejmech.2016.04.002]
44. Deck LM, Whalen LJ, Hunsaker LA, Royer RE, Vander Jagt DL..  (2017)  Activation of anti-oxidant Nrf2 signaling by substituted trans stilbenes.,  25  (4): [PMID:28126440] [10.1016/j.bmc.2017.01.005]
45. Psurski M, Janczewski Ł, Świtalska M, Gajda A, Goszczyński TM, Oleksyszyn J, Wietrzyk J, Gajda T..  (2017)  Novel phosphonate analogs of sulforaphane: Synthesis, in vitro and in vivo anticancer activity.,  132  [PMID:28342398] [10.1016/j.ejmech.2017.03.028]
46. Jiang Y, Li HY, Li XH, Lu J, Zhang Q, Bai CG, Chen Y..  (2018)  Therapeutic effects of isothiocyanate prodrugs on rheumatoid arthritis.,  28  (4): [PMID:29395981] [10.1016/j.bmcl.2018.01.009]
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