2,6,8-trihydroxy-1-[(2S)-2-hydroxy-3-methylbut-3-enyl]xanthen-9-one

Details

• Internal ID: d822d99b-ee68-415f-a389-b5d70cfe5c4f
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 8-prenylated xanthones
• IUPAC Name: 2,6,8-trihydroxy-1-[(2S)-2-hydroxy-3-methylbut-3-enyl]xanthen-9-one
• SMILES (Canonical): CC(=C)C(CC1=C(C=CC2=C1C(=O)C3=C(C=C(C=C3O2)O)O)O)O
• SMILES (Isomeric): CC(=C)[C@H](CC1=C(C=CC2=C1C(=O)C3=C(C=C(C=C3O2)O)O)O)O
• InChI: InChI=1S/C18H16O6/c1-8(2)12(21)7-10-11(20)3-4-14-16(10)18(23)17-13(22)5-9(19)6-15(17)24-14/h3-6,12,19-22H,1,7H2,2H3/t12-/m0/s1
• InChI Key: YBIZIJLYKSWSGG-LBPRGKRZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆O₆
• Molecular Weight: 328.30 g/mol
• Exact Mass: 328.09468823 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.54
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9873	98.73%
Caco-2	+	0.5142	51.42%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5645	56.45%
OATP2B1 inhibitior	-	0.5539	55.39%
OATP1B1 inhibitior	+	0.8188	81.88%
OATP1B3 inhibitior	+	0.9413	94.13%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7386	73.86%
P-glycoprotein inhibitior	-	0.8367	83.67%
P-glycoprotein substrate	-	0.7880	78.80%
CYP3A4 substrate	+	0.5174	51.74%
CYP2C9 substrate	-	0.5826	58.26%
CYP2D6 substrate	-	0.8167	81.67%
CYP3A4 inhibition	+	0.5928	59.28%
CYP2C9 inhibition	-	0.5215	52.15%
CYP2C19 inhibition	+	0.6178	61.78%
CYP2D6 inhibition	-	0.8081	80.81%
CYP1A2 inhibition	+	0.7303	73.03%
CYP2C8 inhibition	+	0.5501	55.01%
CYP inhibitory promiscuity	+	0.7512	75.12%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6757	67.57%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.6219	62.19%
Skin irritation	-	0.6623	66.23%
Skin corrosion	-	0.9050	90.50%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6443	64.43%
Micronuclear	+	0.5859	58.59%
Hepatotoxicity	+	0.5051	50.51%
skin sensitisation	-	0.6113	61.13%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6095	60.95%
Acute Oral Toxicity (c)	III	0.4427	44.27%
Estrogen receptor binding	+	0.7218	72.18%
Androgen receptor binding	+	0.7310	73.10%
Thyroid receptor binding	+	0.6506	65.06%
Glucocorticoid receptor binding	+	0.8598	85.98%
Aromatase binding	+	0.6934	69.34%
PPAR gamma	+	0.8718	87.18%
Honey bee toxicity	-	0.8701	87.01%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9823	98.23%

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	98.30%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.86%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	95.54%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.44%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	91.64%	94.73%
CHEMBL4040	P28482	MAP kinase ERK2	90.30%	83.82%
CHEMBL1929	P47989	Xanthine dehydrogenase	88.51%	96.12%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.28%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.51%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.48%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.29%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.04%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.03%	94.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.53%	93.65%
CHEMBL3194	P02766	Transthyretin	81.26%	90.71%

Plants that contains it

• Hypericum scabrum

Cross-Links

• PubChem: 162936268
• LOTUS: LTS0226106
• wikiData: Q105278386