Catechin 3-rhamnoside

Details

• Internal ID: 1e041219-814b-4d37-959d-8ef66c94eaf1
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CC3=C(C=C(C=C3OC2C4=CC(=C(C=C4)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CC3=C(C=C(C=C3O[C@@H]2C4=CC(=C(C=C4)O)O)O)O)O)O)O
• InChI: InChI=1S/C21H24O10/c1-8-17(26)18(27)19(28)21(29-8)31-16-7-11-13(24)5-10(22)6-15(11)30-20(16)9-2-3-12(23)14(25)4-9/h2-6,8,16-28H,7H2,1H3/t8-,16-,17-,18+,19+,20+,21-/m0/s1
• InChI Key: KYLFHITXPCWYAL-HLBABLIESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₁₀
• Molecular Weight: 436.40 g/mol
• Exact Mass: 436.13694696 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): 0.40
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

• 103630-03-1
• Catechin 3-rhamside
• (2S,3R,4R,5R,6S)-2-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]-6-methyloxane-3,4,5-triol
• Catechin 3-O--L-rhamnopyranoside
• Catechin 3-O-|A-L-rhamnopyranoside
• (2R)-2,3-Dihydro-2alpha-(3,4-dihydroxyphenyl)-3beta-(alpha-L-rhamnopyranosyloxy)-4H-1-benzopyran-5,7-diol
• -L-Mannopyranoside, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl 6-deoxy-, (2R-trans)-; (2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl 6-deoxy--L-mannopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7701	77.01%
Caco-2	-	0.8194	81.94%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6490	64.90%
OATP2B1 inhibitior	-	0.5744	57.44%
OATP1B1 inhibitior	+	0.9051	90.51%
OATP1B3 inhibitior	+	0.8831	88.31%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6717	67.17%
P-glycoprotein inhibitior	-	0.7591	75.91%
P-glycoprotein substrate	-	0.8556	85.56%
CYP3A4 substrate	+	0.5921	59.21%
CYP2C9 substrate	-	0.8007	80.07%
CYP2D6 substrate	-	0.7594	75.94%
CYP3A4 inhibition	-	0.9077	90.77%
CYP2C9 inhibition	-	0.8197	81.97%
CYP2C19 inhibition	-	0.6968	69.68%
CYP2D6 inhibition	-	0.9426	94.26%
CYP1A2 inhibition	-	0.8321	83.21%
CYP2C8 inhibition	+	0.6173	61.73%
CYP inhibitory promiscuity	-	0.7504	75.04%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5513	55.13%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.8435	84.35%
Skin irritation	-	0.7134	71.34%
Skin corrosion	-	0.9230	92.30%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7290	72.90%
Micronuclear	+	0.7859	78.59%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8772	87.72%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7043	70.43%
Acute Oral Toxicity (c)	III	0.4915	49.15%
Estrogen receptor binding	-	0.5564	55.64%
Androgen receptor binding	+	0.5310	53.10%
Thyroid receptor binding	+	0.7352	73.52%
Glucocorticoid receptor binding	+	0.6034	60.34%
Aromatase binding	-	0.5320	53.20%
PPAR gamma	+	0.5832	58.32%
Honey bee toxicity	-	0.7776	77.76%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6150	61.50%
Fish aquatic toxicity	+	0.8704	87.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.84%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.57%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.63%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.86%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.07%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.85%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.14%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.28%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.42%	94.73%
CHEMBL4208	P20618	Proteasome component C5	85.56%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.19%	97.36%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.39%	93.40%
CHEMBL3194	P02766	Transthyretin	82.77%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.43%	95.89%
CHEMBL2535	P11166	Glucose transporter	81.23%	98.75%

Plants that contains it

• Adenia volkensii
• Baccharis angustifolia
• Carallia brachiata
• Cistus × incanus
• Cornus walteri
• Euphorbia clarkeana
• Excoecaria agallocha
• Koompassia malaccensis
• Osyris alba
• Quercus glauca
• Quercus miyagii
• Rhizophora stylosa

Cross-Links

• PubChem: 21626704
• NPASS: NPC222970
• LOTUS: LTS0078673
• wikiData: Q105147764