Catharticin

Details

• Internal ID: 1602593e-1378-49ec-8e32-4b5ae0de9734
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5R,6R)-6-[[(2R,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2O)OCC3C(C(C(C(O3)OC4=C(OC5=CC(=CC(=C5C4=O)O)OC)C6=CC=C(C=C6)O)O)O)O)C)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@H]([C@@H]2O)OC[C@@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)OC4=C(OC5=CC(=CC(=C5C4=O)O)OC)C6=CC=C(C=C6)O)O)O)O)C)O)O)O)O
• InChI: InChI=1S/C34H42O19/c1-11-20(37)24(41)26(43)33(49-11)52-30-21(38)12(2)48-32(28(30)45)47-10-18-22(39)25(42)27(44)34(51-18)53-31-23(40)19-16(36)8-15(46-3)9-17(19)50-29(31)13-4-6-14(35)7-5-13/h4-9,11-12,18,20-22,24-28,30,32-39,41-45H,10H2,1-3H3/t11-,12-,18+,20-,21-,22-,24+,25-,26+,27+,28+,30+,32+,33-,34-/m0/s1
• InChI Key: MQMTVWHXCSRCER-BZPRNGGBSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₂O₁₉
• Molecular Weight: 754.70 g/mol
• Exact Mass: 754.23202911 g/mol
• Topological Polar Surface Area (TPSA): 293.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.24
• H-Bond Acceptor: 19
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

• 39723-40-5
• Alaternin (glycoside)
• Rhamnocitrin 3-O-beta-D-rhamninoside
• 3-(((2S,3R,4S,5R,6R)-6-((((2R,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one
• 4H-1-Benzopyran-4-one, 3-((O-6-deoxy-alpha-L-mannopyranosyl-(1-3)-O-6-deoxy-alpha-L-mannopyranosyl-(1-6)-beta-D-galactopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-
• 3-[(2S,3R,4S,5R,6R)-6-[[(2R,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
• DTXSID50960327
• C34H42O19
• AKOS040761472
• 3-[[6-O-(3-O-alpha-L-Rhamnopyranosyl-alpha-L-rhamnopyranosyl)-beta-D-galactopyranosyl]oxy]-4',5-dihydroxy-7-methoxyflavone
• 5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-3-yl 6-deoxyhexopyranosyl-(1->3)-6-deoxyhexopyranosyl-(1->6)hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4796	47.96%
Caco-2	-	0.8929	89.29%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6680	66.80%
OATP2B1 inhibitior	-	0.5750	57.50%
OATP1B1 inhibitior	+	0.8769	87.69%
OATP1B3 inhibitior	+	0.9137	91.37%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5110	51.10%
P-glycoprotein inhibitior	-	0.4365	43.65%
P-glycoprotein substrate	+	0.6266	62.66%
CYP3A4 substrate	+	0.6484	64.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8527	85.27%
CYP3A4 inhibition	-	0.9310	93.10%
CYP2C9 inhibition	-	0.9351	93.51%
CYP2C19 inhibition	-	0.9301	93.01%
CYP2D6 inhibition	-	0.9356	93.56%
CYP1A2 inhibition	-	0.9113	91.13%
CYP2C8 inhibition	+	0.7862	78.62%
CYP inhibitory promiscuity	-	0.6965	69.65%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6809	68.09%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9080	90.80%
Skin irritation	-	0.8382	83.82%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.7192	71.92%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.9454	94.54%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.9234	92.34%
Acute Oral Toxicity (c)	III	0.6850	68.50%
Estrogen receptor binding	+	0.8193	81.93%
Androgen receptor binding	+	0.6562	65.62%
Thyroid receptor binding	+	0.5677	56.77%
Glucocorticoid receptor binding	+	0.6482	64.82%
Aromatase binding	+	0.5512	55.12%
PPAR gamma	+	0.7444	74.44%
Honey bee toxicity	-	0.7512	75.12%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8533	85.33%

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	99.53%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.19%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.08%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.34%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.28%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.93%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	94.43%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.18%	99.15%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.39%	95.64%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.26%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	91.90%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.58%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.37%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.37%	97.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.36%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.83%	95.89%
CHEMBL4208	P20618	Proteasome component C5	84.89%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.33%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.27%	97.09%

Plants that contains it

• Lycopodium annotinum
• Rhamnus disperma

Cross-Links

• PubChem: 5748627
• NPASS: NPC52833
• LOTUS: LTS0131862
• wikiData: Q82941478