3-O-Acetyl-4-O-(3-methoxy-4-hydroxy-trans-cinnamoyl)-alpha-L-rhamnopyranose

Details

• Internal ID: 7e947e73-b380-48fc-b1bc-6430ea6a9e53
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2S,3S,4S,5R,6R)-4-acetyloxy-5,6-dihydroxy-2-methyloxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• InChI: InChI=1S/C18H22O9/c1-9-16(17(26-10(2)19)15(22)18(23)25-9)27-14(21)7-5-11-4-6-12(20)13(8-11)24-3/h4-9,15-18,20,22-23H,1-3H3/b7-5+/t9-,15+,16-,17-,18+/m0/s1
• InChI Key: SQIGDVPANOZNPA-QNFKXIHRSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₂O₉
• Molecular Weight: 382.40 g/mol
• Exact Mass: 382.12638228 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.36
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8203	82.03%
Caco-2	-	0.7763	77.63%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6987	69.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8824	88.24%
OATP1B3 inhibitior	+	0.9335	93.35%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7622	76.22%
P-glycoprotein inhibitior	-	0.6801	68.01%
P-glycoprotein substrate	-	0.8248	82.48%
CYP3A4 substrate	+	0.5731	57.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8621	86.21%
CYP3A4 inhibition	-	0.8441	84.41%
CYP2C9 inhibition	-	0.9405	94.05%
CYP2C19 inhibition	-	0.8806	88.06%
CYP2D6 inhibition	-	0.9137	91.37%
CYP1A2 inhibition	-	0.8340	83.40%
CYP2C8 inhibition	+	0.5301	53.01%
CYP inhibitory promiscuity	-	0.7606	76.06%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9111	91.11%
Carcinogenicity (trinary)	Non-required	0.5398	53.98%
Eye corrosion	-	0.9706	97.06%
Eye irritation	-	0.9148	91.48%
Skin irritation	-	0.7298	72.98%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7581	75.81%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.6216	62.16%
skin sensitisation	-	0.8957	89.57%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.8361	83.61%
Acute Oral Toxicity (c)	III	0.4589	45.89%
Estrogen receptor binding	+	0.5878	58.78%
Androgen receptor binding	-	0.5530	55.30%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.6057	60.57%
Aromatase binding	-	0.6662	66.62%
PPAR gamma	-	0.6560	65.60%
Honey bee toxicity	-	0.7798	77.98%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5445	54.45%
Fish aquatic toxicity	+	0.9552	95.52%

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	99.35%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.40%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.70%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.60%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.56%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.63%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	93.45%	91.49%
CHEMBL3194	P02766	Transthyretin	91.48%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.09%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	87.27%	94.73%
CHEMBL4208	P20618	Proteasome component C5	84.68%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.00%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.65%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.84%	95.50%

Plants that contains it

• Buddleja asiatica

Cross-Links

• PubChem: 102394753
• LOTUS: LTS0178580
• wikiData: Q105257948