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1-methoxy-3-indolylmethyl glucosinolate

Family: Plantae - Cruciferae-Brassicaceea
Kingdom: Plantae
Class: Alkaloid
- Subclass: Indole Alkaloid

Canonical Smiles	OC[C@H]1O[C@@H](S/C(=N\OS(=O)(=O)O)/Cc2cn(c3c2cccc3)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C17H22N2O10S2/c1-27-19-7-9(10-4-2-3-5-11(10)19)6-13(18-29-31(24,25)26)30-17-16(23)15(22)14(21)12(8-20)28-17/h2-5,7,12,14-17,20-23H,6,8H2,1H3,(H,24,25,26)/b18-13-/t12-,14-,15+,16-,17+/m1/s1
InChIKey	PKKMITFKYRCCOL-JMZFCNQTSA-N
Formula	C₁₇H₂₂N₂O₁₀S₂
HBA	12
HBD	5
MW	478.5
Rotatable Bonds	7
TPSA	180.27
LogP	-1.09
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.47
Exact Mass	478.07
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Moricandia arvensis	Cruciferae-Brassicaceea	Plantae	180540

Showing of synonyms

Belkhiri A, Lockwood GB (1990). An indole derivative and glucosinolates from Moricandia arvensis.. Phytochemistry,1990,29(4),1315-1316. [View]

Pubchem: 9576416

Cas: 5187-84-8

Gnps: CCMSLIB00000211840

Zinc: ZINC000013550565

Nmrshiftdb2: 60068160

CPRiL: 167217

SMILES: O1CCCCC1SC(=N)Cc2c[nH]c(c23)cccc3

Level: 1

Mol. Weight: 478.5 g/mol

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 478.5 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 478.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.59
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.16
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.41

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.86
Plasma Protein Binding: 87.78
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 0.69
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -0.47
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.77
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.64
Micronucleos: Toxic
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: -35.84
Rat (Acute): 2.2
Rat (Chronic Oral): 3.27
Fathead Minnow: 4.1
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 513.45
Hydration Free Energy: -5.36
Log(D) at pH=7.4: -0.63
Log(P): -2.27
Log S: -1.83
Log(Vapor Pressure): -14.26
Melting Point: 132.69
pKa Acid: 3.14
pKa Basic: 4.66

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.9489
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.9489
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9402
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9402
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9099
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9099
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8802
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8802
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.8668
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.8668
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.8598
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.8598
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8559
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8559
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	3	0.8355
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	3	0.8355
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	3	0.8294
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	3	0.8294
Protein mono-ADP-ribosyltransferase PARP14	Q460N5	PAR14_HUMAN	Homo sapiens	3	0.8228
Protein mono-ADP-ribosyltransferase PARP14	Q460N5	PAR14_HUMAN	Homo sapiens	3	0.8228
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.8010
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.8010
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7961
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7961
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7898
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7898
Diamine acetyltransferase 1	P21673	SAT1_HUMAN	Homo sapiens	3	0.7860
Diamine acetyltransferase 1	P21673	SAT1_HUMAN	Homo sapiens	3	0.7860
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7784
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7784
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7768
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7768
Poly [ADP-ribose] polymerase 1	P26446	PARP1_CHICK	Gallus gallus	3	0.7718
Poly [ADP-ribose] polymerase 1	P26446	PARP1_CHICK	Gallus gallus	3	0.7718
Deoxycytidylate deaminase	H6WFU3	H6WFU3_9CAUD	Cyanophage S-TIM5	4	0.7709
Deoxycytidylate deaminase	H6WFU3	H6WFU3_9CAUD	Cyanophage S-TIM5	4	0.7709
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7620
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7620
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7620
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7620
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	4	0.7612
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7612
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	4	0.7612
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7612
L-methionine gamma-lyase	Q84AR1	Q84AR1_CITFR	Citrobacter freundii	4	0.7556
L-methionine gamma-lyase	Q84AR1	Q84AR1_CITFR	Citrobacter freundii	4	0.7556
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7483
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7483
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7462
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7462
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	B1MKD5	B1MKD5_MYCA9	Mycobacteroides abscessus	3	0.7413
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	B1MKD5	B1MKD5_MYCA9	Mycobacteroides abscessus	3	0.7413
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7402
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7402
Hydroxymethylglutaryl-CoA synthase	Q9FD71	HMGCS_ENTFL	Enterococcus faecalis	2	0.7336
Hydroxymethylglutaryl-CoA synthase	Q9FD71	HMGCS_ENTFL	Enterococcus faecalis	2	0.7336
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7331
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7331
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7294
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7294
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	3	0.7275
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	3	0.7275
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7260
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7260
Epothilone C/D epoxidase	Q9KIZ4	C167_SORCE	Sorangium cellulosum	3	0.7249
Epothilone C/D epoxidase	Q9KIZ4	C167_SORCE	Sorangium cellulosum	3	0.7249
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7235
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7235
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7217
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7217
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7200
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7200
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7171
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7171
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7165
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7165
Glutathione S-transferase	Q8ILQ7	GST_PLAFA	Plasmodium falciparum	3	0.7152
Glutathione S-transferase	Q8ILQ7	GST_PLAFA	Plasmodium falciparum	3	0.7152
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7143
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7143
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7128
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7128
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7123
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7123
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7118
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7118
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7118
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7118
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7107
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7107
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7103
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7103
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7084
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7084
Cysteine synthase	P45040	CYSK_HAEIN	Haemophilus influenzae	3	0.7071
Cysteine synthase	P45040	CYSK_HAEIN	Haemophilus influenzae	3	0.7071
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7066
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7066
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7063
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7063
2'-5'-oligoadenylate synthase 1	P00973	OAS1_HUMAN	Homo sapiens	2	0.7057
2'-5'-oligoadenylate synthase 1	P00973	OAS1_HUMAN	Homo sapiens	2	0.7057
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7022
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7022
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7019
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7019
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7007
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7007
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	4	0.7005
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	4	0.7005

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