1-(1-b-Glucopyranosyl)-1H-indole-3-acetic acid

Details

• Internal ID: 965c625f-e399-4cbc-b38d-8dece0933a1b
• Taxonomy: Nucleosides, nucleotides, and analogues > Nucleoside and nucleotide analogues > 1-pyranosylindoles
• IUPAC Name: 2-[1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]indol-3-yl]acetic acid
• SMILES (Canonical): C1=CC=C2C(=C1)C(=CN2C3C(C(C(C(O3)CO)O)O)O)CC(=O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=CN2C3C(C(C(C(O3)CO)O)O)O)CC(=O)O
• InChI: InChI=1S/C16H19NO7/c18-7-11-13(21)14(22)15(23)16(24-11)17-6-8(5-12(19)20)9-3-1-2-4-10(9)17/h1-4,6,11,13-16,18,21-23H,5,7H2,(H,19,20)
• InChI Key: MVSQEPAOMLRIRW-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₉NO₇
• Molecular Weight: 337.32 g/mol
• Exact Mass: 337.11615195 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.76
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6335	63.35%
Caco-2	-	0.8905	89.05%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Nucleus	0.3495	34.95%
OATP2B1 inhibitior	-	0.8620	86.20%
OATP1B1 inhibitior	+	0.9040	90.40%
OATP1B3 inhibitior	+	0.9400	94.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9566	95.66%
BSEP inhibitior	-	0.8649	86.49%
P-glycoprotein inhibitior	-	0.8894	88.94%
P-glycoprotein substrate	-	0.9295	92.95%
CYP3A4 substrate	-	0.5197	51.97%
CYP2C9 substrate	-	0.7914	79.14%
CYP2D6 substrate	-	0.8190	81.90%
CYP3A4 inhibition	-	0.9639	96.39%
CYP2C9 inhibition	-	0.9348	93.48%
CYP2C19 inhibition	-	0.9344	93.44%
CYP2D6 inhibition	-	0.9399	93.99%
CYP1A2 inhibition	-	0.7985	79.85%
CYP2C8 inhibition	-	0.8161	81.61%
CYP inhibitory promiscuity	-	0.9060	90.60%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5577	55.77%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9495	94.95%
Skin irritation	-	0.7998	79.98%
Skin corrosion	-	0.9430	94.30%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6333	63.33%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	+	0.5767	57.67%
skin sensitisation	-	0.8832	88.32%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8827	88.27%
Acute Oral Toxicity (c)	III	0.4444	44.44%
Estrogen receptor binding	-	0.7502	75.02%
Androgen receptor binding	-	0.5824	58.24%
Thyroid receptor binding	-	0.6106	61.06%
Glucocorticoid receptor binding	-	0.5331	53.31%
Aromatase binding	-	0.5197	51.97%
PPAR gamma	+	0.7553	75.53%
Honey bee toxicity	-	0.9101	91.01%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	-	0.6916	69.16%

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	96.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.04%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.31%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.00%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.60%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	87.58%	94.23%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.23%	96.61%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.03%	94.62%
CHEMBL3401	O75469	Pregnane X receptor	81.94%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.04%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.49%	99.23%

Plants that contains it

• Ribes rubrum

Cross-Links

• PubChem: 74428158
• LOTUS: LTS0024155
• wikiData: Q77279266