Swertipunicoside

Details

• Internal ID: 8dedc16e-0f4e-4d1c-8df6-4b21d639e191
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,3,6,7-tetrahydroxy-2-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4-(1,4,8-trihydroxy-6-methoxy-9-oxoxanthen-2-yl)xanthen-9-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC3=C(C=C(C(=C3C2=O)O)C4=C5C(=C(C(=C4O)C6C(C(C(C(O6)CO)O)O)O)O)C(=O)C7=CC(=C(C=C7O5)O)O)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC3=C(C=C(C(=C3C2=O)O)C4=C5C(=C(C(=C4O)[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)C(=O)C7=CC(=C(C=C7O5)O)O)O)O
• InChI: InChI=1S/C33H26O17/c1-47-8-2-13(37)19-16(3-8)49-31-14(38)5-10(24(40)20(31)27(19)43)18-26(42)22(33-30(46)29(45)25(41)17(7-34)50-33)28(44)21-23(39)9-4-11(35)12(36)6-15(9)48-32(18)21/h2-6,17,25,29-30,33-38,40-42,44-46H,7H2,1H3/t17-,25-,29+,30-,33+/m1/s1
• InChI Key: GNMLPEJAIRBAAO-FLJAPRSHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₂₆O₁₇
• Molecular Weight: 694.50 g/mol
• Exact Mass: 694.11699936 g/mol
• Topological Polar Surface Area (TPSA): 294.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.34
• H-Bond Acceptor: 17
• H-Bond Donor: 11
• Rotatable Bonds: 4

Synonyms

• 137570-21-9
• CHEBI:66538
• (2,4'-Bi-9H-xanthene)-9,9'-dione, 2'-beta-D-glucopyranosyl-1,1',3',4,6',7',8-heptahydroxy-6-methoxy-
• 1,3,6,7-tetrahydroxy-2-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4-(1,4,8-trihydroxy-6-methoxy-9-oxoxanthen-2-yl)xanthen-9-one
• (1S)-1,5-anhydro-1-(1,1',3',4,6',7',8-heptahydroxy-6-methoxy-9,9'-dioxo-9H,9'H-2,4'-bixanthen-2'-yl)-D-glucitol
• 1,5,8-Trihydroxy-3-methoxy-7-(1',3',6',7'-tetrahydroxy-9'-oxo-4'-xanthyl)xanthone-2'-C-beta-D-glucopyranoside
• CHEMBL502311
• DTXSID00160239
• Q27135146
• [2,4'-Bi-9H-xanthene]-9,9'-dione, 2'-.beta.-D-glucopyranosyl-1,1',3',4,6',7',8-heptahydroxy-6-methoxy-
• 1,3,6,7-tetrahydroxy-2-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]-4-(1,4,8-trihydroxy-6-methoxy-9-oxo-xanthen-2-yl)xanthen-9-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5519	55.19%
Caco-2	-	0.9078	90.78%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5780	57.80%
OATP2B1 inhibitior	-	0.5606	56.06%
OATP1B1 inhibitior	+	0.7730	77.30%
OATP1B3 inhibitior	+	0.9876	98.76%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8279	82.79%
P-glycoprotein inhibitior	+	0.6382	63.82%
P-glycoprotein substrate	-	0.5137	51.37%
CYP3A4 substrate	+	0.6766	67.66%
CYP2C9 substrate	-	0.8129	81.29%
CYP2D6 substrate	-	0.8347	83.47%
CYP3A4 inhibition	-	0.8280	82.80%
CYP2C9 inhibition	-	0.8292	82.92%
CYP2C19 inhibition	-	0.8671	86.71%
CYP2D6 inhibition	-	0.9475	94.75%
CYP1A2 inhibition	-	0.8377	83.77%
CYP2C8 inhibition	+	0.6895	68.95%
CYP inhibitory promiscuity	-	0.7816	78.16%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7066	70.66%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.8993	89.93%
Skin irritation	-	0.8231	82.31%
Skin corrosion	-	0.9496	94.96%
Ames mutagenesis	+	0.7135	71.35%
Human Ether-a-go-go-Related Gene inhibition	+	0.6765	67.65%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	-	0.6592	65.92%
skin sensitisation	-	0.9230	92.30%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7683	76.83%
Acute Oral Toxicity (c)	III	0.6151	61.51%
Estrogen receptor binding	+	0.8127	81.27%
Androgen receptor binding	+	0.7280	72.80%
Thyroid receptor binding	+	0.5237	52.37%
Glucocorticoid receptor binding	+	0.6212	62.12%
Aromatase binding	-	0.4927	49.27%
PPAR gamma	+	0.6600	66.00%
Honey bee toxicity	-	0.7079	70.79%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.6612	66.12%

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	99.74%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.00%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.69%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.66%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.61%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	94.08%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.38%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.82%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.42%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.21%	97.09%
CHEMBL204	P00734	Thrombin	85.77%	96.01%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.54%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.46%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.97%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.83%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.83%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	83.56%	94.73%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	82.09%	88.00%
CHEMBL1907	P15144	Aminopeptidase N	81.53%	93.31%
CHEMBL226	P30542	Adenosine A1 receptor	81.51%	95.93%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.19%	92.62%

Plants that contains it

• Swertia calycina
• Swertia punicea

Cross-Links

• PubChem: 5321573
• LOTUS: LTS0199628
• wikiData: Q27135146