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Isothiocyanatomethyl benzene

Family: Plantae - Cruciferae-Brassicaceea
Kingdom: Plantae
Class: Monoaromatic
- Subclass: Thiocyanate

Canonical Smiles	S=C=NCc1ccccc1
InChI	InChI=1S/C8H7NS/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2
InChIKey	MDKCFLQDBWCQCV-UHFFFAOYSA-N
Formula	C₈H₇NS
HBA	2
HBD	0
MW	149.22
Rotatable Bonds	2
TPSA	12.36
LogP	2.29
Number Rings	1
Number Aromatic Rings	1
Heavy Atom Count	10
Formal Charge	0
Fraction CSP3	0.12
Exact Mass	149.03
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Cleome chrysantha	Capparaceae	Plantae	1522775
2	Erucaria microcarpa	Cruciferae-Brassicaceea	Plantae	1078594

Showing of synonyms

Hashem FA, Saleh MM (1999). Antimicrobial components of some cruciferae plants (Diplotaxis harra Forsk. and Erucaria microcarpa Boiss.).. Phytotherapy Research,1999,13(4),329-332. [View]
Hashem FA, Wahba HE (2000). Isothiocyanates in myrosinase treated herb extract of Cleome chrysantha Decne. and their antimicrobial activities. Phytotherapy Research,2000,14,284-287. [View] [PubMed]

Pubchem: 2346

Cas: 622-78-6

Zinc: ZINC000001529592

Kegg Ligand: C03098

Chebi: 17484

Nmrshiftdb2: 60018532

Chembl: CHEMBL55285

Comptox: DTXSID0020155

Drugbank: DB16860

Bindingdb: 50240520

CPRiL: 10066

SMILES: c1ccccc1

Level: 0

Mol. Weight: 149.22 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.15
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -3.960
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.29

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.400
Plasma Protein Binding: 38.19
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 6.860
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.090
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Toxic
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.740
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.800
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 4.700
Rat (Acute): 2.690
Rat (Chronic Oral): 1.570
Fathead Minnow: 4.770
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Toxic
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 238.360
Hydration Free Energy: -3.270
Log(D) at pH=7.4: 2.810
Log(P): 3.23
Log S: -3.16
Log(Vapor Pressure): -1.69
Melting Point: 0.56
pKa Acid: 8.84
pKa Basic: 0.96

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA methylase	Q8DSS3	Q8DSS3_STRMU	Streptococcus mutans serotype c	2	0.8470
rRNA methylase	Q8DSS3	Q8DSS3_STRMU	Streptococcus mutans serotype c	2	0.8470
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	2	0.8407
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	2	0.8407
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	2	0.7982
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	2	0.7982
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7742
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7742
Toluene-4-monooxygenase system, hydroxylase component subunit alpha	Q00456	TMOA_PSEME	Pseudomonas mendocina	2	0.7645
Toluene-4-monooxygenase system, hydroxylase component subunit alpha	Q00456	TMOA_PSEME	Pseudomonas mendocina	2	0.7645
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic	P49235	HGGL1_MAIZE	Zea mays	2	0.7639
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic	P49235	HGGL1_MAIZE	Zea mays	2	0.7639
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7626
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7626
Kallikrein-4	Q9Y5K2	KLK4_HUMAN	Homo sapiens	2	0.7511
Kallikrein-4	Q9Y5K2	KLK4_HUMAN	Homo sapiens	2	0.7511
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7437
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7437
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	2	0.7435
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	2	0.7435
Glutamate receptor ionotropic, kainate 1	P22756	GRIK1_RAT	Rattus norvegicus	2	0.7398
Glutamate receptor ionotropic, kainate 1	P22756	GRIK1_RAT	Rattus norvegicus	2	0.7398
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7366
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7366
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	2	0.7348
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	2	0.7348
Alpha/beta hydrolase fold protein	D2J2T6	D2J2T6_9RHIZ	Ochrobactrum sp. T63	2	0.7337
Alpha/beta hydrolase fold protein	D2J2T6	D2J2T6_9RHIZ	Ochrobactrum sp. T63	2	0.7337
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7301
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7301
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7295
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7295
Kallikrein-4	Q9Y5K2	KLK4_HUMAN	Homo sapiens	2	0.7273
Kallikrein-4	Q9Y5K2	KLK4_HUMAN	Homo sapiens	2	0.7273
Succinyl-CoA:acetate CoA-transferase	B3EY95	SCACT_ACEAC	Acetobacter aceti	2	0.7264
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7264
Succinyl-CoA:acetate CoA-transferase	B3EY95	SCACT_ACEAC	Acetobacter aceti	2	0.7264
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7264
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	2	0.7252
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	2	0.7252
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	2	0.7249
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	2	0.7249
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7247
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7247
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	2	0.7245
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	2	0.7245
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	2	0.7241
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	2	0.7241
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7212
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7212
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7209
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7209
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	2	0.7189
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	2	0.7189
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7180
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7180
Class B acid phosphatase	P0AE22	APHA_ECOLI	Escherichia coli	2	0.7165
Class B acid phosphatase	P0AE22	APHA_ECOLI	Escherichia coli	2	0.7165
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	2	0.7138
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	2	0.7138
Tryptophan synthase alpha chain	P00929	TRPA_SALTY	Salmonella typhimurium	2	0.7126
Tryptophan synthase alpha chain	P00929	TRPA_SALTY	Salmonella typhimurium	2	0.7126
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7120
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7120
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7114
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7114
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7111
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7111
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2	O95340	PAPS2_HUMAN	Homo sapiens	2	0.7104
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2	O95340	PAPS2_HUMAN	Homo sapiens	2	0.7104
Phosphotriesterase	Q5KZU5	Q5KZU5_GEOKA	Geobacillus kaustophilus	2	0.7103
Phosphotriesterase	Q5KZU5	Q5KZU5_GEOKA	Geobacillus kaustophilus	2	0.7103
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7099
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7099
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7092
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7092
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7087
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7087
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7076
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7076
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7071
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7071
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7071
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7071
adenine phosphoribosyltransferase	Q967M2	Q967M2_GIAIN	Giardia intestinalis	2	0.7042
adenine phosphoribosyltransferase	Q967M2	Q967M2_GIAIN	Giardia intestinalis	2	0.7042
SKP1-like protein 1A	Q39255	SKP1A_ARATH	Arabidopsis thaliana	2	0.7037
SKP1-like protein 1A	Q39255	SKP1A_ARATH	Arabidopsis thaliana	2	0.7037
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7032
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7032
Proline iminopeptidase	O32449	PIP_SERMA	Serratia marcescens	2	0.7026
Proline iminopeptidase	O32449	PIP_SERMA	Serratia marcescens	2	0.7026
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7019
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7019
Mandelate racemase	P11444	MANR_PSEPU	Pseudomonas putida	2	0.7015
SKP1-like protein 1A	Q39255	SKP1A_ARATH	Arabidopsis thaliana	2	0.7015
SKP1-like protein 1A	Q39255	SKP1A_ARATH	Arabidopsis thaliana	2	0.7015
Mandelate racemase	P11444	MANR_PSEPU	Pseudomonas putida	2	0.7015
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7013
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	2	0.7013
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7013
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	2	0.7013
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	2	0.7012
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	2	0.7012
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7006
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7006
clade A/E 93TH057 HIV-1 gp120 core	A0A0M3KKW9	A0A0M3KKW9_9HIV1	Human immunodeficiency virus 1	2	0.7003
clade A/E 93TH057 HIV-1 gp120 core	A0A0M3KKW9	A0A0M3KKW9_9HIV1	Human immunodeficiency virus 1	2	0.7003

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