methyl (2S)-5-hydroxy-1-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydroindole-2-carboxylate

Details

• Internal ID: d738eb64-45ab-40ea-be8f-16e34d6d7836
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: methyl (2S)-5-hydroxy-1-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydroindole-2-carboxylate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)N2C(CC3=CC(=C(C=C32)OC4C(C(C(C(O4)CO)O)O)O)O)C(=O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)N2[C@@H](CC3=CC(=C(C=C32)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C(=O)OC)O
• InChI: InChI=1S/C26H29NO12/c1-36-18-7-12(3-5-16(18)29)4-6-21(31)27-14-10-19(17(30)9-13(14)8-15(27)25(35)37-2)38-26-24(34)23(33)22(32)20(11-28)39-26/h3-7,9-10,15,20,22-24,26,28-30,32-34H,8,11H2,1-2H3/b6-4+/t15-,20+,22+,23-,24+,26+/m0/s1
• InChI Key: KNUYHEQHOCPQAW-AFBSOZDYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₉NO₁₂
• Molecular Weight: 547.50 g/mol
• Exact Mass: 547.16897536 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.57
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6661	66.61%
Caco-2	-	0.8944	89.44%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.3663	36.63%
OATP2B1 inhibitior	-	0.8498	84.98%
OATP1B1 inhibitior	+	0.8727	87.27%
OATP1B3 inhibitior	+	0.9379	93.79%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7995	79.95%
P-glycoprotein inhibitior	-	0.4405	44.05%
P-glycoprotein substrate	-	0.5800	58.00%
CYP3A4 substrate	+	0.6457	64.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8479	84.79%
CYP3A4 inhibition	-	0.8383	83.83%
CYP2C9 inhibition	-	0.7526	75.26%
CYP2C19 inhibition	-	0.8142	81.42%
CYP2D6 inhibition	-	0.9273	92.73%
CYP1A2 inhibition	-	0.8276	82.76%
CYP2C8 inhibition	+	0.5906	59.06%
CYP inhibitory promiscuity	-	0.7163	71.63%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4913	49.13%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9382	93.82%
Skin irritation	-	0.8104	81.04%
Skin corrosion	-	0.9437	94.37%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3999	39.99%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	-	0.7771	77.71%
skin sensitisation	-	0.8829	88.29%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7402	74.02%
Acute Oral Toxicity (c)	III	0.6744	67.44%
Estrogen receptor binding	+	0.8655	86.55%
Androgen receptor binding	+	0.6253	62.53%
Thyroid receptor binding	+	0.5727	57.27%
Glucocorticoid receptor binding	+	0.6717	67.17%
Aromatase binding	-	0.5604	56.04%
PPAR gamma	+	0.6165	61.65%
Honey bee toxicity	-	0.7942	79.42%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.7849	78.49%

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	99.22%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.83%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.12%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.86%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.31%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	93.18%	89.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.30%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.90%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.11%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.00%	98.95%
CHEMBL4208	P20618	Proteasome component C5	89.14%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.05%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.92%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.71%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	82.46%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.81%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.40%	90.71%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.34%	97.14%

Plants that contains it

• Portulaca oleracea

Cross-Links

• PubChem: 52914108
• LOTUS: LTS0096417
• wikiData: Q105143595