4-Hydroxyglucobrassicin

Details

• Internal ID: 85b7c373-5429-4e53-823d-a8e1940aee6c
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glucosinolates > Alkylglucosinolates
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2-(4-hydroxy-1H-indol-3-yl)-N-sulfooxyethanimidothioate
• SMILES (Canonical): C1=CC2=C(C(=C1)O)C(=CN2)CC(=NOS(=O)(=O)O)SC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C1=CC2=C(C(=C1)O)C(=CN2)CC(=NOS(=O)(=O)O)S[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C16H20N2O10S2/c19-6-10-13(21)14(22)15(23)16(27-10)29-11(18-28-30(24,25)26)4-7-5-17-8-2-1-3-9(20)12(7)8/h1-3,5,10,13-17,19-23H,4,6H2,(H,24,25,26)/t10-,13-,14+,15-,16+/m1/s1
• InChI Key: CSMYCLLHRFFFLG-IRHMCKRBSA-N
• Popularity: 16 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀N₂O₁₀S₂
• Molecular Weight: 464.50 g/mol
• Exact Mass: 464.05593719 g/mol
• Topological Polar Surface Area (TPSA): 236.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.92
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

• 4-Hydroxy-3-indolylmethylglucosinolate
• C08422
• 83327-20-2
• AC1LCV7A
• C16H20N2O10S2
• C16-H20-N2-O10-S2
• [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2-(4-hydroxy-1H-indol-3-yl)-N-sulfooxyethanimidothioate
• 4- Hydroxyglucobrassicin (4-Hydroxy-3-indomethyl-GS)
• Q27105513
• [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] 2-(4-hydroxy-1H-indol-3-yl)-N-sulfooxy-ethanimidothioate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5565	55.65%
Caco-2	-	0.9007	90.07%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Lysosomes	0.3411	34.11%
OATP2B1 inhibitior	-	0.8514	85.14%
OATP1B1 inhibitior	+	0.8761	87.61%
OATP1B3 inhibitior	+	0.9388	93.88%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.5695	56.95%
P-glycoprotein inhibitior	-	0.7267	72.67%
P-glycoprotein substrate	-	0.6889	68.89%
CYP3A4 substrate	+	0.6189	61.89%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.8355	83.55%
CYP3A4 inhibition	-	0.8214	82.14%
CYP2C9 inhibition	-	0.7241	72.41%
CYP2C19 inhibition	-	0.6876	68.76%
CYP2D6 inhibition	-	0.8513	85.13%
CYP1A2 inhibition	-	0.6492	64.92%
CYP2C8 inhibition	-	0.5668	56.68%
CYP inhibitory promiscuity	-	0.7060	70.60%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.5584	55.84%
Carcinogenicity (trinary)	Non-required	0.5507	55.07%
Eye corrosion	-	0.9723	97.23%
Eye irritation	-	0.9172	91.72%
Skin irritation	-	0.7571	75.71%
Skin corrosion	-	0.9039	90.39%
Ames mutagenesis	+	0.6176	61.76%
Human Ether-a-go-go-Related Gene inhibition	-	0.5731	57.31%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8283	82.83%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.5754	57.54%
Acute Oral Toxicity (c)	III	0.5550	55.50%
Estrogen receptor binding	+	0.6547	65.47%
Androgen receptor binding	-	0.5518	55.18%
Thyroid receptor binding	-	0.5536	55.36%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6352	63.52%
PPAR gamma	+	0.5833	58.33%
Honey bee toxicity	-	0.7215	72.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5955	59.55%
Fish aquatic toxicity	+	0.7838	78.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.35%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.61%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.31%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.21%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.62%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.96%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	92.55%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.49%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	90.15%	94.75%
CHEMBL3401	O75469	Pregnane X receptor	89.10%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	87.87%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.91%	86.92%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.61%	93.99%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.57%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.05%	89.00%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	83.49%	82.86%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.40%	92.88%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.93%	96.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.85%	100.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.46%	89.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.63%	95.89%

Plants that contains it

• Isatis tinctoria
• Persicaria tinctoria

Cross-Links

• PubChem: 656561
• NPASS: NPC277404