Tosylphenylalanyl chloromethyl ketone

Details

• Internal ID: f24258ff-3d15-4dfc-859a-194c4cf5f80c
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Toluenes > Tosyl compounds > P-toluenesulfonamides
• IUPAC Name: N-[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]-4-methylbenzenesulfonamide
• SMILES (Canonical): CC1=CC=C(C=C1)S(=O)(=O)NC(CC2=CC=CC=C2)C(=O)CCl
• SMILES (Isomeric): CC1=CC=C(C=C1)S(=O)(=O)N[C@@H](CC2=CC=CC=C2)C(=O)CCl
• InChI: InChI=1S/C17H18ClNO3S/c1-13-7-9-15(10-8-13)23(21,22)19-16(17(20)12-18)11-14-5-3-2-4-6-14/h2-10,16,19H,11-12H2,1H3/t16-/m0/s1
• InChI Key: MQUQNUAYKLCRME-INIZCTEOSA-N
• Popularity: 537 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈ClNO₃S
• Molecular Weight: 351.80 g/mol
• Exact Mass: 351.0695923 g/mol
• Topological Polar Surface Area (TPSA): 71.60 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 2.69
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• TOSYLPHENYLALANYL CHLOROMETHYL KETONE
• N-Tosyl-L-phenylalanyl chloromethyl ketone
• N-Tosyl-L-phenylalanine chloromethyl ketone
• L-1-Tosylamido-2-phenylethyl chloromethyl ketone
• l-N-(alpha-(Chloroacetyl)phenethyl)-p-toluenesulfonamide
• CHEBI:9642
• DTXSID60883376
• N-[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]-4-methylbenzenesulfonamide
• P598716LJT
• NSC-727365
• Benzenesulfonamide, N-(3-chloro-2-oxo-1-(phenylmethyl)propyl)-4-methyl-, (S)-
• Chlorophenyltosylamidobutanone
• Tosylphenylalanyl Chloromethane
• Chloromethane, Tosylphenylalanyl
• N-((2S)-4-chloro-3-oxo-1-phenylbutan-2-yl)-4-methylbenzenesulfonamide
• Benzenesulfonamide, N-[3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-, (S)-
• Chloromethyl Ketone, Tosylphenylalanyl
• Ketone, Tosylphenylalanyl Chloromethyl
• RefChem:831186
• Nalpha-Tosyl-L-Phenylalanine Chloromethyl Ketone
• DTXCID001022912
• 206-954-6
• TPCK
• N-p-Tosyl-L-phenylalanine chloromethyl ketone
• Tos-Phe-CH2Cl
• (S)-N-(4-Chloro-3-oxo-1-phenylbutan-2-yl)-4-methylbenzenesulfonamide
• Benzenesulfonamide,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-
• Tos-Phe-chloromethylketone
• MFCD00000935
• tosylphenylalanylchloromethane
• CHEMBL60718
• MLS000028752
• SMR000058518
• p-Toluenesulfonamide, N-(alpha-(chloroacetyl)phenethyl)-, (-)-
• L-1-p-Tosylamino-2-phenylethyl chloromethyl ketone
• N-(p-Toluenesulfonyl)-L-phenylalanine chloromethyl ketone
• N-[(1S)-1-benzyl-3-chloro-2-oxo-propyl]-4-methyl-benzenesulfonamide
• N-?-Tosyl-L-phenylalanylchloromethane
• Benzenesulfonamide, N-((1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl)-4-methyl-
• Benzenesulfonamide, N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-
• EINECS 206-954-6
• Tosylphenylalanyl chloromethyl ketone, (L)-
• BRN 2895215
• L-1-Tosylamide-2-phenylethylchloromethyl Ketone
• Opera_ID_1094
• Lopac-T-4376
• Tosyl-Phe-CMK (TPCK)
• L-1-TOSYLAMIDE-2-PHENYLETHYL-CHLOROMETHYL KETONE
• Lopac0_001157
• BSPBio_001541
• KBioGR_000261
• KBioSS_000261
• MLS001076075
• MLS006010721
• SCHEMBL927265
• UNII-P598716LJT
• AC1L97R8
• cid_439647
• orb1299011
• SCHEMBL6331296
• Tosyl-L-phenylalanylchloromethane
• KBio2_000261
• KBio2_002829
• KBio2_005397
• KBio3_000521
• KBio3_000522
• BRD5988
• Bio2_000261
• Bio2_000741
• HMS1361N03
• HMS1791N03
• HMS1989N03
• HMS3263H15
• HMS3402N03
• N-Tosyl-L-phenylalanylchloromethane
• (S)-N-(4-Chloro-3-oxo-1-phenyl-2-butyl)-p-toluenesulfonamide
• BRD-5988
• L-Chloromethyl (2-phenyl-1-(p-toluenesulphonylamino)ethyl) ketone
• Tox21_501157
• BDBM50085363
• CAS329306
• NSC727365
• PI-122
• AKOS027327594
• CCG-205231
• LP01157
• NSC 727365
• SDCCGSBI-0051124.P003
• IDI1_034011
• n-alpha-tosyl-l-phenylalanylchloromethane
• NCGC00016020-01
• NCGC00094419-01
• NCGC00094419-02
• NCGC00094419-03
• NCGC00094419-04
• NCGC00094419-05
• NCGC00094419-06
• NCGC00094419-07
• NCGC00261842-01
• AS-35326
• p-Tosyl-L-phenylalanine chloromethylketone
• SY075507
• N-TOSYL-L-PHENYLALANINECHLOROMETHANE
• HY-124379
• CS-0086323
• EU-0101157
• N-P-tosyl-L-phenylalanyl chloromethyl ketone
• TOSYLPHENYLALANINE CHLOROMETHYL KETONE
• C02088
• L-1-Tosylamido-2-phenylethylchloromethyl ketone
• N-TOSYLPHENYLALANINE CHLOROMETHYL KETONE
• T 4376
• N-.ALPHA.-TOSYL-L-PHENYLALANYLCHLOROMETHANE
• SR-01000076157
• Q7827912
• SR-01000076157-1
• BRD-K07055988-001-02-4
• L-1-CHLORO-3-TOSYLAMIDYL-4-PHENYL-2-BUTANONE
• L-TOLYLSULFONYLPHENYLALANYL CHLOROMETHYL KETONE
• N-p-Tosyl-L-phenylalanine chloromethyl ketone (TPCK)
• N-(P-TOLUENESULFONYL)-L-PHENYLALANYLCHLOROMETHANE
• .ALPHA.-N-TOSYL-L-PHENYLALANINE CHLOROMETHYL KETONE
• l-N-(.alpha.-(Chloroacetyl)phenethyl)-p-toluenesulfonamide
• N.ALPHA.-TOSYL-L-PHENYLALANINE CHLOROMETHYL KETONE
• (3S)-3-(p-Toluenesulfonyl)amino-1-chloro-4-phenyl-2-butanone
• L-([Toluene-4-sulfonamido]-2-phenyl)ethyl chloromethyl ketone
• L-1-CHLORO-4-PHENYL-3-P-TOLYLSULFONAMIDOBUTAN-2-ONE
• L-1-CHLORO-4-PHENYL-3-TOLUENE-P-SULFONAMIDO-2-BUTANONE
• p-Toluenesulfonamide, N-(.alpha.-(chloroacetyl)phenethyl)-, (-)-
• N-p-Tosyl-L-phenylalanine chloromethyl ketone, >=97% (TLC), powder
• P-TOLUENESULFONAMIDE, N-(.ALPHA.-(CHLOROACETYL)PHENETHYL)-, L-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	-	0.5837	58.37%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5935	59.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9360	93.60%
OATP1B3 inhibitior	+	0.9439	94.39%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8483	84.83%
P-glycoprotein inhibitior	-	0.8813	88.13%
P-glycoprotein substrate	-	0.7876	78.76%
CYP3A4 substrate	-	0.5660	56.60%
CYP2C9 substrate	-	0.7747	77.47%
CYP2D6 substrate	-	0.7889	78.89%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.8563	85.63%
CYP inhibitory promiscuity	+	0.8727	87.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5096	50.96%
Carcinogenicity (trinary)	Non-required	0.6302	63.02%
Eye corrosion	-	0.9634	96.34%
Eye irritation	-	0.8897	88.97%
Skin irritation	-	0.7756	77.56%
Skin corrosion	-	0.9129	91.29%
Ames mutagenesis	-	0.5270	52.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8361	83.61%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8610	86.10%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	-	0.6111	61.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5680	56.80%
Acute Oral Toxicity (c)	III	0.6822	68.22%
Estrogen receptor binding	+	0.6068	60.68%
Androgen receptor binding	-	0.5329	53.29%
Thyroid receptor binding	-	0.7956	79.56%
Glucocorticoid receptor binding	-	0.7987	79.87%
Aromatase binding	-	0.5776	57.76%
PPAR gamma	-	0.7071	70.71%
Honey bee toxicity	-	0.9356	93.56%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9817	98.17%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	17782.8 nM; 19952.6 nM	Potency; Potency	via CMAUP; PMID: 19459694
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	794.3 nM; 398.1 nM; 1000 nM; 398.1 nM	Potency; Potency; Potency; Potency	PMID: 2362284; via Super-PRED; PMID: 22182501; PMID: 19874044
CHEMBL4096	P04637	Cellular tumor antigen p53	6309.6 nM; 3162.3 nM	Potency; Potency	PMID: 22694318; PMID: 12502321
CHEMBL4068	P23946	Chymase	3300 nM	IC50	PMID: 25871261
CHEMBL3356	P05177	Cytochrome P450 1A2	12589.25 nM	AC50	PMID: 18332176
CHEMBL3622	P33261	Cytochrome P450 2C19	10000 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	19952.6 nM	Potency	PMID: 9733489
CHEMBL340	P08684	Cytochrome P450 3A4	3162.3 nM; 3162.3 nM	Potency; Potency	PMID: 21925888; via CMAUP
CHEMBL1293278	O75496	Geminin	3162.3 nM	Potency	PMID: 15620251
CHEMBL5514	P42858	Huntingtin	35481.3 nM	Potency	PMID: 22260257
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	25118.9 nM; 25118.9 nM	Potency; Potency	PMID: 11543673; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	19952.6 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	8912.5 nM; 112.2 nM; 7079.5 nM	Potency; Potency; Potency	PMID: 1602298; PMID: 21090801; PMID: 24694263
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	12589.3 nM; 19952.6 nM	Potency; Potency	PMID: 19105653; PMID: 18183025
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	3162.3 nM; 3162.3 nM	Potency; Potency	DOI: 10.1007/s00044-009-9206-8; PMID: 22548480
CHEMBL1293298	Q01453	Peripheral myelin protein 22	30131.3 nM	Potency	PMID: 19064900
CHEMBL1293235	P02545	Prelamin-A/C	7079.5 nM; 2818.4 nM; 14125.4 nM	Potency; Potency; Potency	PMID: 14698171; PMID: 23305465; PMID: 23891163
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	23280.9 nM; 20749.1 nM; 18492.7 nM; 16481.6 nM	Potency; Potency; Potency; Potency	PMID: 2578192; PMID: 22070654; PMID: 11931609; PMID: 18417256
CHEMBL1293232	Q16637	Survival motor neuron protein	28183.8 nM; 17782.8 nM; 1000 nM	Potency; Potency; Potency	via CMAUP; DOI: 10.6019/CHEMBL1201861; PMID: 25938459
CHEMBL1293256	P40225	Thrombopoietin	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	31622.8 nM	Potency	PMID: 26355532

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.48%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.76%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	95.85%	90.17%
CHEMBL1741221	Q9Y4P1	Cysteine protease ATG4B	94.18%	87.50%
CHEMBL3401	O75469	Pregnane X receptor	93.32%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.72%	96.09%
CHEMBL3902	P09211	Glutathione S-transferase Pi	84.49%	93.81%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.42%	93.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.00%	93.03%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.67%	96.90%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.06%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.74%	96.00%
CHEMBL5932	P53671	LIM domain kinase 2	80.69%	96.49%

Plants that contains it

• Cyanthillium cinereum

Cross-Links

• PubChem: 439647
• NPASS: NPC476440
• ChEMBL: CHEMBL60718
• LOTUS: LTS0006770
• wikiData: Q7827912