1,3,6,7-tetrahydroxy-2-[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]xanthen-9-one

Details

• Internal ID: ac2156c7-cb4a-4fb2-bf59-1b043c404a59
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 1,3,6,7-tetrahydroxy-2-[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]xanthen-9-one
• SMILES (Canonical): C1=C2C(=CC(=C1O)O)OC3=C(C2=O)C(=C(C(=C3)O)C4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C1=C2C(=CC(=C1O)O)OC3=C(C2=O)C(=C(C(=C3)O)[C@@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C19H18O11/c20-4-11-15(25)17(27)18(28)19(30-11)12-8(23)3-10-13(16(12)26)14(24)5-1-6(21)7(22)2-9(5)29-10/h1-3,11,15,17-23,25-28H,4H2/t11-,15-,17+,18-,19+/m0/s1
• InChI Key: AEDDIBAIWPIIBD-XQOGOWKJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₁₁
• Molecular Weight: 422.30 g/mol
• Exact Mass: 422.08491139 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.72
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6665	66.65%
Caco-2	-	0.9063	90.63%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5728	57.28%
OATP2B1 inhibitior	+	0.5917	59.17%
OATP1B1 inhibitior	+	0.8457	84.57%
OATP1B3 inhibitior	+	0.9709	97.09%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.7832	78.32%
P-glycoprotein inhibitior	-	0.8199	81.99%
P-glycoprotein substrate	-	0.8329	83.29%
CYP3A4 substrate	+	0.5332	53.32%
CYP2C9 substrate	-	0.6301	63.01%
CYP2D6 substrate	-	0.8452	84.52%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9240	92.40%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.8355	83.55%
CYP2C8 inhibition	-	0.7195	71.95%
CYP inhibitory promiscuity	-	0.7806	78.06%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7252	72.52%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.7527	75.27%
Skin irritation	-	0.7691	76.91%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	+	0.5709	57.09%
Human Ether-a-go-go-Related Gene inhibition	-	0.5358	53.58%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8683	86.83%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9060	90.60%
Acute Oral Toxicity (c)	IV	0.3746	37.46%
Estrogen receptor binding	+	0.6269	62.69%
Androgen receptor binding	+	0.6656	66.56%
Thyroid receptor binding	-	0.4912	49.12%
Glucocorticoid receptor binding	+	0.7460	74.60%
Aromatase binding	-	0.4858	48.58%
PPAR gamma	+	0.5653	56.53%
Honey bee toxicity	-	0.7452	74.52%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.6921	69.21%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5573	P09923	Intestinal alkaline phosphatase	262 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.41%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.45%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.53%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.84%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.64%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	87.32%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.29%	96.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.03%	99.23%

Plants that contains it

• Hedysarum denticulatum
• Iris ensata

Cross-Links

• PubChem: 124461561
• LOTUS: LTS0049988
• wikiData: Q104910001