8-hydroxy-3,5-dimethoxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyxanthen-9-one

Details

• Internal ID: 5785b078-41b8-4b91-b8b7-553d027d7708
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 8-hydroxy-3,5-dimethoxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyxanthen-9-one
• SMILES (Canonical): COC1=C2C(=C(C=C1)O)C(=O)C3=C(O2)C=C(C=C3OC4C(C(C(C(O4)COC5C(C(C(C(O5)CO)O)O)O)O)O)O)OC
• SMILES (Isomeric): COC1=C2C(=C(C=C1)O)C(=O)C3=C(O2)C=C(C=C3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)OC
• InChI: InChI=1S/C27H32O16/c1-37-9-5-12-17(20(32)16-10(29)3-4-11(38-2)25(16)40-12)13(6-9)41-27-24(36)22(34)19(31)15(43-27)8-39-26-23(35)21(33)18(30)14(7-28)42-26/h3-6,14-15,18-19,21-24,26-31,33-36H,7-8H2,1-2H3/t14-,15-,18-,19-,21+,22+,23-,24-,26-,27-/m1/s1
• InChI Key: AHBKLQCFFXMAJT-YUMVGKRXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₆
• Molecular Weight: 612.50 g/mol
• Exact Mass: 612.16903493 g/mol
• Topological Polar Surface Area (TPSA): 244.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -2.33
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6956	69.56%
Caco-2	-	0.8973	89.73%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5635	56.35%
OATP2B1 inhibitior	-	0.8506	85.06%
OATP1B1 inhibitior	+	0.8952	89.52%
OATP1B3 inhibitior	+	0.9723	97.23%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6476	64.76%
P-glycoprotein inhibitior	-	0.5432	54.32%
P-glycoprotein substrate	-	0.6510	65.10%
CYP3A4 substrate	+	0.5990	59.90%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9364	93.64%
CYP2C9 inhibition	-	0.9521	95.21%
CYP2C19 inhibition	-	0.9234	92.34%
CYP2D6 inhibition	-	0.9259	92.59%
CYP1A2 inhibition	-	0.9313	93.13%
CYP2C8 inhibition	+	0.5605	56.05%
CYP inhibitory promiscuity	-	0.8225	82.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6598	65.98%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9224	92.24%
Skin irritation	-	0.8449	84.49%
Skin corrosion	-	0.9681	96.81%
Ames mutagenesis	+	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7283	72.83%
Micronuclear	+	0.5733	57.33%
Hepatotoxicity	-	0.8073	80.73%
skin sensitisation	-	0.9231	92.31%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.6430	64.30%
Acute Oral Toxicity (c)	III	0.7432	74.32%
Estrogen receptor binding	+	0.8328	83.28%
Androgen receptor binding	+	0.5609	56.09%
Thyroid receptor binding	-	0.4902	49.02%
Glucocorticoid receptor binding	+	0.5854	58.54%
Aromatase binding	+	0.6077	60.77%
PPAR gamma	+	0.7337	73.37%
Honey bee toxicity	-	0.8099	80.99%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6449	64.49%
Fish aquatic toxicity	-	0.4096	40.96%

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	99.16%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.38%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.25%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.82%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.61%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.24%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.01%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	89.51%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.87%	86.92%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.74%	85.14%
CHEMBL3194	P02766	Transthyretin	86.58%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.46%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.64%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.49%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.23%	94.45%
CHEMBL4208	P20618	Proteasome component C5	84.85%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.72%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.17%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.10%	97.36%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.32%	92.62%

Plants that contains it

• Swertia kouitchensis

Cross-Links

• PubChem: 71745144
• LOTUS: LTS0076985
• wikiData: Q104912161