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4-(alpha-L-rhamnosyloxy)benzyl isothiocyanate

Family: Plantae - Moringaceae
Kingdom: Plantae
Class: Thiocyanate
- Subclass: Isothiocyanate

Canonical Smiles	S=C=NCc1ccc(cc1)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
InChI	InChI=1S/C14H17NO5S/c1-8-11(16)12(17)13(18)14(19-8)20-10-4-2-9(3-5-10)6-15-7-21/h2-5,8,11-14,16-18H,6H2,1H3/t8-,11-,12+,13+,14-/m0/s1
InChIKey	QAZIHHJTZPNRCM-CNJBRALLSA-N
Formula	C₁₄H₁₇NO₅S
HBA	7
HBD	3
MW	311.36
Rotatable Bonds	4
TPSA	91.51
LogP	0.5
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	311.08
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Moringa peregrina	Moringaceae	Plantae	161031

Showing of synonyms

Kær A, Malver O, et al. (1979). Isothiocyanates in Myrosinase-treated Seeds Extract of Moringa Peregrina. Phytochemistry, 1979, 18(9), 1485-1487. [View]

Pubchem: 153557

Cas: 73255-40-0

Nmrshiftdb2: 80008609

Chembl: CHEMBL1223970

CPRiL: 115582

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 311.36 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 311.36 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 311.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.47
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.510
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.52

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.540
Plasma Protein Binding: 68.77
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: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 3.480
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.380
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.270
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.880
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: 0.550
Rat (Acute): 2.710
Rat (Chronic Oral): 2.350
Fathead Minnow: 4.060
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 388.740
Hydration Free Energy: -16.520
Log(D) at pH=7.4: 1.210
Log(P): 1.59
Log S: -2.62
Log(Vapor Pressure): -10.0
Melting Point: 132.29
pKa Acid: 8.0
pKa Basic: 2.02

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9364
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.9212
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8996
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8901
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8794
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8681
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8657
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8608
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8591
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8560
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8530
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8471
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.8431
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8421
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8347
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8317
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.8158
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8082
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7950
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.7940
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7892
Beta-glucosidase 12	B8AVF0	BGL12_ORYSI	Oryza sativa subsp. indica	3	0.7834
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7827
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7770
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7769
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7723
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7707
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7706
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7680
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7565
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7556
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7529
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7505
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7492
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7472
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7465
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7464
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7430
CCR4-NOT transcription complex subunit 6-like	Q96LI5	CNO6L_HUMAN	Homo sapiens	4	0.7388
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7386
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7384
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7373
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7361
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7341
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7336
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7334
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7296
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7292
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7281
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7248
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7243
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7236
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7218
Purine nucleoside phosphorylase	Q8I3X4	Q8I3X4_PLAF7	Plasmodium falciparum	3	0.7217
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7199
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7198
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	2	0.7197
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7192
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7191
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7189
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7170
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7160
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7141
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7133
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7131
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7128
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7127
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7127
Beta-glucosidase	Q8T0W7	Q8T0W7_9NEOP	Neotermes koshunensis	3	0.7126
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7113
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7101
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7090
Granule-bound starch synthase 1, chloroplastic/amyloplastic	Q0DEV5	SSG1_ORYSJ	Oryza sativa subsp. japonica	3	0.7077
Predicted acetyltransferase	Q97ML2	Q97ML2_CLOAB	Clostridium acetobutylicum	3	0.7075
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7073
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7058
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7040
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7036
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7028
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	3	0.7019

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