1,3,6,7-Tetrahydroxy-2-(2-methylbut-3-en-2-yl)-8-(3-methylbut-2-enyl)xanthen-9-one

Details

• Internal ID: 1dbdcd0e-ac2a-4f33-babc-b4b092e3c964
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 8-prenylated xanthones
• IUPAC Name: 1,3,6,7-tetrahydroxy-2-(2-methylbut-3-en-2-yl)-8-(3-methylbut-2-enyl)xanthen-9-one
• SMILES (Canonical): CC(=CCC1=C(C(=CC2=C1C(=O)C3=C(O2)C=C(C(=C3O)C(C)(C)C=C)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=CC2=C1C(=O)C3=C(O2)C=C(C(=C3O)C(C)(C)C=C)O)O)O)C
• InChI: InChI=1S/C23H24O6/c1-6-23(4,5)19-13(24)9-16-18(22(19)28)21(27)17-12(8-7-11(2)3)20(26)14(25)10-15(17)29-16/h6-7,9-10,24-26,28H,1,8H2,2-5H3
• InChI Key: UVBQFJQAVCIWKR-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₆
• Molecular Weight: 396.40 g/mol
• Exact Mass: 396.15728848 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 4.74
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9508	95.08%
Caco-2	-	0.5312	53.12%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5546	55.46%
OATP2B1 inhibitior	-	0.5532	55.32%
OATP1B1 inhibitior	+	0.8978	89.78%
OATP1B3 inhibitior	+	0.9702	97.02%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5217	52.17%
P-glycoprotein inhibitior	-	0.6204	62.04%
P-glycoprotein substrate	-	0.7754	77.54%
CYP3A4 substrate	+	0.5424	54.24%
CYP2C9 substrate	-	0.6013	60.13%
CYP2D6 substrate	-	0.8438	84.38%
CYP3A4 inhibition	-	0.7928	79.28%
CYP2C9 inhibition	+	0.7149	71.49%
CYP2C19 inhibition	+	0.7505	75.05%
CYP2D6 inhibition	-	0.7212	72.12%
CYP1A2 inhibition	+	0.6926	69.26%
CYP2C8 inhibition	-	0.6225	62.25%
CYP inhibitory promiscuity	+	0.6888	68.88%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7195	71.95%
Eye corrosion	-	0.9892	98.92%
Eye irritation	+	0.6731	67.31%
Skin irritation	-	0.6981	69.81%
Skin corrosion	-	0.8660	86.60%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4523	45.23%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.6845	68.45%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7977	79.77%
Acute Oral Toxicity (c)	III	0.6083	60.83%
Estrogen receptor binding	+	0.7864	78.64%
Androgen receptor binding	+	0.7076	70.76%
Thyroid receptor binding	+	0.5596	55.96%
Glucocorticoid receptor binding	+	0.7713	77.13%
Aromatase binding	+	0.6320	63.20%
PPAR gamma	+	0.8325	83.25%
Honey bee toxicity	-	0.8120	81.20%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9961	99.61%

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	98.59%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	96.12%	94.73%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	96.02%	89.34%
CHEMBL2581	P07339	Cathepsin D	95.55%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.18%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.04%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.48%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.95%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	83.34%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.22%	94.45%
CHEMBL3038469	P24941	CDK2/Cyclin A	80.08%	91.38%

Plants that contains it

• Maclura tricuspidata

Cross-Links

• PubChem: 44156959
• NPASS: NPC45146
• ChEMBL: CHEMBL249948
• LOTUS: LTS0228957
• wikiData: Q105279739