3-isothiocyanatoprop-1-ene

ID: ALA233248

Chembl Id: CHEMBL233248

Cas Number: 57-06-7

PubChem CID: 5971

Product Number: A477314

Max Phase: Phase

Molecular Formula: C4H5NS

Molecular Weight: 99.16

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Allyl isothiocyanate | Allyl isothiocyanate, stabilized | Mustard oil | Oil, mustard | Oil,mustard | FEMA NO. 2034 | NSC-5572 | ALLYL ISOTHIOCYANATE|57-06-7|3-isothiocyanatoprop-1-ene|AITC|Redskin|ALLYLISOTHIOCYANATE|Allylsenevol|Allylsenfoel|Oleum sinapis|Allylsevenolum|Senfoel|Allyl isosulfocyanate|1-Propene, 3-isothiocyanato-|Allyspol|Carbospol|3-Isothiocyanato-1-propene|2-Propenyl isothiocyanate|Senf oel|Oleum sinapis volatile|Isothiocyanate d'allyle|Allyl sevenolum|8007-40-7|Isothiocyanic aShow More

Canonical SMILES:  C=CCN=C=S

Standard InChI:  InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2

Standard InChI Key:  ZOJBYZNEUISWFT-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

Associated Targets(Human)

TRPA1 Tclin Transient receptor potential cation channel subfamily A member 1 (1847 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KAT2A Tchem Histone acetyltransferase GCN5 (14285 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR1H4 Tclin Bile acid receptor FXR (6228 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TP53 Tchem Cellular tumor antigen p53 (48468 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
MIF Tchem Macrophage migration inhibitory factor (979 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TRPV1 Tclin Vanilloid receptor (8273 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
LoVo (4724 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Mycobacterium tuberculosis (203094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium avium (4587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trpa1 Transient receptor potential cation channel subfamily A member 1 (58 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Tribolium confusum (93 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Sitophilus oryzae (115 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plodia interpunctella (8 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trifolium repens (19 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dactylis glomerata (15 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cyperus iria (145 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Echinochloa crus-galli (3685 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Meloidogyne javanica (98 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Sclerotinia sclerotiorum (877 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trpm8 Transient receptor potential cation channel subfamily M member 8 (202 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (11336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 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: 99.16Molecular Weight (Monoisotopic): 99.0143AlogP: 1.28#Rotatable Bonds: 2
Polar Surface Area: 12.36Molecular Species: NEUTRALHBA: 2HBD: 0
#RO5 Violations: 0HBA (Lipinski): 1HBD (Lipinski): 0#RO5 Violations (Lipinski): 0
CX Acidic pKa: CX Basic pKa: 0.65CX LogP: 1.80CX LogD: 1.80
Aromatic Rings: 0Heavy Atoms: 6QED Weighted: 0.29Np Likeness Score: 0.20

References

1. Chiba T, Takii T, Nishimura K, Yamamoto Y, Morikawa H, Abe C, Onozaki K..  (2007)  Synthesis of new sugar derivatives from Stachys sieboldi Miq and antibacterial evaluation against Mycobacterium tuberculosis, Mycobacterium avium, and Staphylococcus aureus.,  17  (9): [PMID:17331717] [10.1016/j.bmcl.2007.02.024]
2. Macpherson LJ, Dubin AE, Evans MJ, Marr F, Schultz PG, Cravatt BF, Patapoutian A..  (2007)  Noxious compounds activate TRPA1 ion channels through covalent modification of cysteines.,  445  (7127): [PMID:17237762] [10.1038/nature05544]
3. Baraldi PG, Preti D, Materazzi S, Geppetti P..  (2010)  Transient receptor potential ankyrin 1 (TRPA1) channel as emerging target for novel analgesics and anti-inflammatory agents.,  53  (14): [PMID:20356305] [10.1021/jm100062h]
4. Voets T, Talavera K, Owsianik G, Nilius B..  (2005)  Sensing with TRP channels.,  (2): [PMID:16408004] [10.1038/nchembio0705-85]
5. Gijsen HJ, Berthelot D, Zaja M, Brône B, Geuens I, Mercken M..  (2010)  Analogues of morphanthridine and the tear gas dibenz[b,f][1,4]oxazepine (CR) as extremely potent activators of the human transient receptor potential ankyrin 1 (TRPA1) channel.,  53  (19): [PMID:20806939] [10.1021/jm100477n]
6. PubChem BioAssay data set, 
7. Ryckmans T, Aubdool AA, Aubdool AA, Bodkin JV, Cox P, Brain SD, Dupont T, Fairman E, Hashizume Y, Ishii N, Kato T, Kitching L, Newman J, Omoto K, Rawson D, Strover J..  (2011)  Design and pharmacological evaluation of PF-4840154, a non-electrophilic reference agonist of the TrpA1 channel.,  21  (16): [PMID:21741838] [10.1016/j.bmcl.2011.06.035]
8. Morera E, De Petrocellis L, Morera L, Moriello AS, Nalli M, Di Marzo V, Ortar G..  (2012)  Synthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators.,  22  (4): [PMID:22257892] [10.1016/j.bmcl.2011.12.113]
9. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 
10. 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]
11. Mansour EltayebE, Mi Fengyu, Zhang Guoan, Jiugao Xie, Wang Yongmo, Kargbo Abu..  (2012)  Effect of allylisothiocyanate on Sitophilus oryzae, Tribolium confusum and Plodia interpunctella: Toxicity and effect on insect mitochondria,  33  [10.1016/j.cropro.2011.11.010]
12. Wu H, Wang CJ, Bian XW, Zeng SY, Lin KC, Wu B, Zhang G, Zhang X..  (2011)  Nematicidal efficacy of isothiocyanates against root-knot nematode Meloidogyne javanica in cucumber,  30  (1): [10.1016/j.cropro.2010.09.004]
13. Wu H, Feng JT, Lin KC, Zhang X..  (2012)  Synthesis and herbicidal activity of substituted pyrazole isothiocyanates.,  17  (10): [PMID:23075815] [10.3390/molecules171012187]
14. Kurt S, Güneş U, Soylu EM..  (2011)  In vitro and in vivo antifungal activity of synthetic pure isothiocyanates against Sclerotinia sclerotiorum.,  67  (7): [PMID:21370393] [10.1002/ps.2126]
15. 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]
16. Terada Y, Horie S, Takayama H, Uchida K, Tominaga M, Watanabe T..  (2014)  Activation and inhibition of thermosensitive TRP channels by voacangine, an alkaloid present in Voacanga africana, an African tree.,  77  (2): [PMID:24484240] [10.1021/np400885u]
17. PubChem BioAssay data set, 
18. PubChem BioAssay data set, 
19. PubChem BioAssay data set, 
20. Del Prete D, Caprioglio D, Appendino G, Minassi A, Schiano-Moriello A, Di Marzo V, De Petrocellis L..  (2015)  Discovery of non-electrophilic capsaicinoid-type TRPA1 ligands.,  25  (5): [PMID:25666822] [10.1016/j.bmcl.2015.01.039]
21. 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]
22. Terada Y, Masuda H, Watanabe T..  (2015)  Structure-Activity Relationship Study on Isothiocyanates: Comparison of TRPA1-Activating Ability between Allyl Isothiocyanate and Specific Flavor Components of Wasabi, Horseradish, and White Mustard.,  78  (8): [PMID:26263397] [10.1021/acs.jnatprod.5b00272]
23. 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]
24. Nakao S, Mabuchi M, Wang S, Kogure Y, Shimizu T, Noguchi K, Tanaka A, Dai Y..  (2017)  Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor.,  27  (14): [PMID:28576617] [10.1016/j.bmcl.2017.05.025]
25. 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]
26. Chandrabalan A, McPhillie MJ, Morice AH, Boa AN, Sadofsky LR..  (2019)  N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites.,  170  [PMID:30878828] [10.1016/j.ejmech.2019.02.074]
27. Hill K, Fiorito S, Taddeo VA, Schulze A, Leonhardt M, Epifano F, Genovese S..  (2016)  Plumbagin, Juglone, and Boropinal as Novel TRPA1 Agonists.,  79  (4): [PMID:26905390] [10.1021/acs.jnatprod.5b00396]
28. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]
29. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]
30. Araki M, Kanda N, Iwata H, Sagae Y, Masuda K, Okuno Y..  (2020)  Identification of a new class of non-electrophilic TRPA1 agonists by a structure-based virtual screening approach.,  30  (11): [PMID:32249116] [10.1016/j.bmcl.2020.127142]
31. Qiao Z, Luo J, Tang YQ, Zhou Q, Qi H, Yin Z, Tang X, Zhu W, Zhang Y, Wei N, Wang K..  (2021)  Photosensitive and Photoswitchable TRPA1 Agonists Optically Control Pain through Channel Desensitization.,  64  (21.0): [PMID:34662118] [10.1021/acs.jmedchem.1c01579]
32. Unpublished dataset,