tryptophan N-glucoside

Details

• Internal ID: 94c444dd-396e-4003-8f44-2d142b0f4b5a
• Taxonomy: Nucleosides, nucleotides, and analogues > Nucleoside and nucleotide analogues > 1-pyranosylindoles
• IUPAC Name: (2S)-2-amino-3-[1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]indol-3-yl]propanoic acid
• InChI: InChI=1S/C17H22N2O7/c18-10(17(24)25)5-8-6-19(11-4-2-1-3-9(8)11)16-15(23)14(22)13(21)12(7-20)26-16/h1-4,6,10,12-16,20-23H,5,7,18H2,(H,24,25)/t10-,12+,13+,14-,15+,16+/m0/s1
• InChI Key: ZHBHZDMTVVJASV-JOSVURMMSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂N₂O₇
• Molecular Weight: 366.40 g/mol
• Exact Mass: 366.14270105 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: -3.60
• Atomic LogP (AlogP): -1.43
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• 1-beta-D-glucopyranosyl-L-tryptophan
• L-tryptophan N-glucoside
• L-tryptophan N-glucopyranoside
• CHEBI:76121
• Q27145767
• (2S)-2-amino-3-[1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]indol-3-yl]propanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5351	53.51%
Caco-2	-	0.8822	88.22%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Nucleus	0.5327	53.27%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.9258	92.58%
OATP1B3 inhibitior	+	0.9425	94.25%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9861	98.61%
BSEP inhibitior	-	0.6515	65.15%
P-glycoprotein inhibitior	-	0.8641	86.41%
P-glycoprotein substrate	-	0.8698	86.98%
CYP3A4 substrate	-	0.5064	50.64%
CYP2C9 substrate	-	0.7968	79.68%
CYP2D6 substrate	-	0.7693	76.93%
CYP3A4 inhibition	-	0.9233	92.33%
CYP2C9 inhibition	-	0.9323	93.23%
CYP2C19 inhibition	-	0.9466	94.66%
CYP2D6 inhibition	-	0.9352	93.52%
CYP1A2 inhibition	-	0.9242	92.42%
CYP2C8 inhibition	-	0.7720	77.20%
CYP inhibitory promiscuity	-	0.9023	90.23%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5378	53.78%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9872	98.72%
Skin irritation	-	0.8024	80.24%
Skin corrosion	-	0.9433	94.33%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6408	64.08%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	+	0.5526	55.26%
skin sensitisation	-	0.8890	88.90%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.8955	89.55%
Acute Oral Toxicity (c)	III	0.4193	41.93%
Estrogen receptor binding	-	0.5937	59.37%
Androgen receptor binding	-	0.5280	52.80%
Thyroid receptor binding	-	0.6070	60.70%
Glucocorticoid receptor binding	-	0.4635	46.35%
Aromatase binding	+	0.6025	60.25%
PPAR gamma	+	0.5632	56.32%
Honey bee toxicity	-	0.8915	89.15%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	-	0.7962	79.62%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.33%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.41%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.45%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.47%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.26%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.91%	94.23%
CHEMBL226	P30542	Adenosine A1 receptor	84.89%	95.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.45%	96.61%
CHEMBL1741221	Q9Y4P1	Cysteine protease ATG4B	80.96%	87.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.59%	97.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.45%	94.62%
CHEMBL3401	O75469	Pregnane X receptor	80.22%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.14%	99.17%

Plants that contains it

• Pyrus communis

Cross-Links

• PubChem: 11772967
• LOTUS: LTS0023633
• wikiData: Q27145767