2,3-dihydroxy-5-methyl-3-[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methoxycarbonyl]hexanoic acid

Details

• Internal ID: 2ad56890-8731-40e1-a8b3-3b3cd3fc6de7
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 2,3-dihydroxy-5-methyl-3-[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methoxycarbonyl]hexanoic acid
• SMILES (Canonical): CC(C)CC(C(C(=O)O)O)(C(=O)OCC1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O)O
• SMILES (Isomeric): CC(C)CC(C(C(=O)O)O)(C(=O)OCC1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
• InChI: InChI=1S/C21H30O12/c1-10(2)7-21(30,17(26)18(27)28)20(29)31-9-11-3-5-12(6-4-11)32-19-16(25)15(24)14(23)13(8-22)33-19/h3-6,10,13-17,19,22-26,30H,7-9H2,1-2H3,(H,27,28)/t13-,14-,15+,16-,17?,19-,21?/m1/s1
• InChI Key: RNPNWXZHTQBCSB-HASLYLMPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₁₂
• Molecular Weight: 474.50 g/mol
• Exact Mass: 474.17372639 g/mol
• Topological Polar Surface Area (TPSA): 203.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.87
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6100	61.00%
Caco-2	-	0.8689	86.89%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8017	80.17%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.9048	90.48%
OATP1B3 inhibitior	+	0.9285	92.85%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8509	85.09%
P-glycoprotein inhibitior	-	0.6615	66.15%
P-glycoprotein substrate	-	0.8478	84.78%
CYP3A4 substrate	+	0.6032	60.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8836	88.36%
CYP3A4 inhibition	-	0.9009	90.09%
CYP2C9 inhibition	-	0.8550	85.50%
CYP2C19 inhibition	-	0.9121	91.21%
CYP2D6 inhibition	-	0.9404	94.04%
CYP1A2 inhibition	-	0.8588	85.88%
CYP2C8 inhibition	-	0.5953	59.53%
CYP inhibitory promiscuity	-	0.9542	95.42%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6791	67.91%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9304	93.04%
Skin irritation	-	0.8524	85.24%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6457	64.57%
Micronuclear	-	0.7026	70.26%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8706	87.06%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8531	85.31%
Acute Oral Toxicity (c)	III	0.6970	69.70%
Estrogen receptor binding	+	0.5630	56.30%
Androgen receptor binding	+	0.6638	66.38%
Thyroid receptor binding	-	0.4912	49.12%
Glucocorticoid receptor binding	+	0.5692	56.92%
Aromatase binding	-	0.5255	52.55%
PPAR gamma	-	0.5543	55.43%
Honey bee toxicity	-	0.8318	83.18%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.8839	88.39%

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	98.42%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.12%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.55%	99.17%
CHEMBL2179	P04062	Beta-glucocerebrosidase	89.83%	85.31%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.69%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	87.67%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.05%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.85%	95.89%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	84.57%	94.97%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.42%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.16%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.90%	95.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.32%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.86%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.32%	95.56%
CHEMBL4208	P20618	Proteasome component C5	81.14%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.91%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.72%	86.33%

Plants that contains it

• Gymnadenia conopsea

Cross-Links

• PubChem: 9804929
• LOTUS: LTS0027885
• wikiData: Q105241748