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3-indolylmethyl glucosinolate

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

Canonical Smiles	OC[C@@H]1O[C@H](O)[C@H]([C@@H]([C@H]1O)On1ccc2c1cccc2)O
InChI	InChI=1S/C14H17NO6/c16-7-10-11(17)13(12(18)14(19)20-10)21-15-6-5-8-3-1-2-4-9(8)15/h1-6,10-14,16-19H,7H2/t10-,11-,12-,13+,14-/m0/s1
InChIKey	WDXKGXOQUMSNJH-YHQUGGNUSA-N
Formula	C₁₄H₁₇NO₆
HBA	7
HBD	4
MW	295.29
Rotatable Bonds	3
TPSA	104.31
LogP	-1.13
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.43
Exact Mass	295.11
Number of Lipinski Rule Violations	0

#	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: 162817366

Nmrshiftdb2: 70072923

No compound-protein relationship available.

SMILES: c1cccc(c12)n(cc2)OC3CCOCC3

Level: 1

Mol. Weight: 295.29 g/mol

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 295.29 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 295.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.19
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -3.960
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.02

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.860
Plasma Protein Binding: 56.26
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: Non-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: 8.780
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -0.820
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.170
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.130
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: -2.580
Rat (Acute): 2.540
Rat (Chronic Oral): 2.920
Fathead Minnow: 3.790
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 402.220
Hydration Free Energy: -16.420
Log(D) at pH=7.4: 0.520
Log(P): -0.47
Log S: -1.88
Log(Vapor Pressure): -10.71
Melting Point: 183.87
pKa Acid: 7.94
pKa Basic: 3.09

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.9027
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.9027
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8841
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8841
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.8803
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.8803
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8619
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8619
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8541
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8541
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	3	0.8519
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	3	0.8519
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8142
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8142
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8080
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8080
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8055
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8055
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8041
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8041
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7996
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7996
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7979
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7979
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7954
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7954
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7950
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7950
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7932
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7932
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7909
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7909
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7894
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7894
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7815
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7815
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7812
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7812
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7745
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7745
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	4	0.7665
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	4	0.7665
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7605
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7605
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7595
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7595
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7554
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7554
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7551
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7551
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7521
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7521
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7470
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7470
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	4	0.7400
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	4	0.7400
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7395
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7395
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7382
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7382
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7359
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7359
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7306
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7306
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7266
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7266
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7189
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7189
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7147
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7147
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7126
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7126
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7118
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7118
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7110
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7110
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7064
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7064
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7036
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7036
Adenosine 5'-monophosphoramidase HINT1	P80912	HINT1_RABIT	Oryctolagus cuniculus	3	0.7029
Adenosine 5'-monophosphoramidase HINT1	P80912	HINT1_RABIT	Oryctolagus cuniculus	3	0.7029
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7018
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7018

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