1,3,6,7-Tetrahydroxy-2-(3-methylbut-2-enyl)xanthone

Details

• Internal ID: b56daa12-7658-46e4-9528-18c0ab097c67
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 2-prenylated xanthones
• IUPAC Name: 1,3,6,7-tetrahydroxy-2-(3-methylbut-2-enyl)xanthen-9-one
• SMILES (Canonical): CC(=CCC1=C(C2=C(C=C1O)OC3=CC(=C(C=C3C2=O)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C2=C(C=C1O)OC3=CC(=C(C=C3C2=O)O)O)O)C
• InChI: InChI=1S/C18H16O6/c1-8(2)3-4-9-11(19)6-15-16(17(9)22)18(23)10-5-12(20)13(21)7-14(10)24-15/h3,5-7,19-22H,4H2,1-2H3
• InChI Key: ACRGTLGOYYTGNX-UHFFFAOYSA-N
• Popularity: 6 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: 4.00
• Atomic LogP (AlogP): 3.28
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9712	97.12%
Caco-2	-	0.5829	58.29%
Blood Brain Barrier	-	0.6379	63.79%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5583	55.83%
OATP2B1 inhibitior	-	0.5385	53.85%
OATP1B1 inhibitior	+	0.9265	92.65%
OATP1B3 inhibitior	+	0.9801	98.01%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5781	57.81%
P-glycoprotein inhibitior	-	0.7606	76.06%
P-glycoprotein substrate	-	0.8092	80.92%
CYP3A4 substrate	-	0.5207	52.07%
CYP2C9 substrate	-	0.6039	60.39%
CYP2D6 substrate	-	0.8389	83.89%
CYP3A4 inhibition	-	0.6501	65.01%
CYP2C9 inhibition	+	0.7858	78.58%
CYP2C19 inhibition	+	0.6792	67.92%
CYP2D6 inhibition	-	0.6287	62.87%
CYP1A2 inhibition	+	0.8400	84.00%
CYP2C8 inhibition	-	0.8021	80.21%
CYP inhibitory promiscuity	+	0.8000	80.00%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7266	72.66%
Eye corrosion	-	0.9886	98.86%
Eye irritation	+	0.7833	78.33%
Skin irritation	-	0.6879	68.79%
Skin corrosion	-	0.8917	89.17%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6825	68.25%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.6572	65.72%
skin sensitisation	-	0.6270	62.70%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8904	89.04%
Acute Oral Toxicity (c)	III	0.5872	58.72%
Estrogen receptor binding	+	0.8889	88.89%
Androgen receptor binding	+	0.7144	71.44%
Thyroid receptor binding	-	0.4882	48.82%
Glucocorticoid receptor binding	+	0.8689	86.89%
Aromatase binding	+	0.7225	72.25%
PPAR gamma	+	0.9254	92.54%
Honey bee toxicity	-	0.8109	81.09%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9915	99.15%

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	99.18%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.25%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	94.37%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	93.05%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.02%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.51%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.60%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.37%	89.34%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.00%	85.14%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	83.80%	83.10%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.48%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.47%	93.99%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.55%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.33%	86.33%

Plants that contains it

• Allanblackia gabonensis
• Hypericum perforatum

Cross-Links

• PubChem: 10314415
• LOTUS: LTS0123164
• wikiData: Q104909247