1,3,5,6-tetrahydroxy-4-[(2S)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]xanthen-9-one

Details

• Internal ID: 417da76d-2443-454a-9a3b-b60f71b20431
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 4-prenylated xanthones
• IUPAC Name: 1,3,5,6-tetrahydroxy-4-[(2S)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]xanthen-9-one
• SMILES (Canonical): CC(=CCC(CC1=C2C(=C(C=C1O)O)C(=O)C3=C(O2)C(=C(C=C3)O)O)C(=C)C)C
• SMILES (Isomeric): CC(=CC[C@@H](CC1=C2C(=C(C=C1O)O)C(=O)C3=C(O2)C(=C(C=C3)O)O)C(=C)C)C
• InChI: InChI=1S/C23H24O6/c1-11(2)5-6-13(12(3)4)9-15-17(25)10-18(26)19-20(27)14-7-8-16(24)21(28)23(14)29-22(15)19/h5,7-8,10,13,24-26,28H,3,6,9H2,1-2,4H3/t13-/m0/s1
• InChI Key: ZXCREOQQIQQVAR-ZDUSSCGKSA-N
• Popularity: 0 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: 5.80
• Atomic LogP (AlogP): 4.86
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9669	96.69%
Caco-2	-	0.7665	76.65%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5142	51.42%
OATP2B1 inhibitior	+	0.5769	57.69%
OATP1B1 inhibitior	+	0.8610	86.10%
OATP1B3 inhibitior	+	0.9671	96.71%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8025	80.25%
P-glycoprotein inhibitior	-	0.5190	51.90%
P-glycoprotein substrate	-	0.5804	58.04%
CYP3A4 substrate	+	0.5455	54.55%
CYP2C9 substrate	+	0.5943	59.43%
CYP2D6 substrate	-	0.8360	83.60%
CYP3A4 inhibition	-	0.7014	70.14%
CYP2C9 inhibition	+	0.7045	70.45%
CYP2C19 inhibition	+	0.6857	68.57%
CYP2D6 inhibition	-	0.7109	71.09%
CYP1A2 inhibition	+	0.7890	78.90%
CYP2C8 inhibition	-	0.6370	63.70%
CYP inhibitory promiscuity	+	0.7180	71.80%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7392	73.92%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.5406	54.06%
Skin irritation	-	0.7016	70.16%
Skin corrosion	-	0.8948	89.48%
Ames mutagenesis	+	0.5936	59.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4300	43.00%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.6501	65.01%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7176	71.76%
Acute Oral Toxicity (c)	III	0.6162	61.62%
Estrogen receptor binding	+	0.8376	83.76%
Androgen receptor binding	+	0.6880	68.80%
Thyroid receptor binding	+	0.7049	70.49%
Glucocorticoid receptor binding	+	0.8726	87.26%
Aromatase binding	+	0.6957	69.57%
PPAR gamma	+	0.9319	93.19%
Honey bee toxicity	-	0.8301	83.01%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9960	99.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.67%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.44%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.28%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.07%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.83%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	91.91%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.28%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	90.47%	89.34%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.31%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.99%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.74%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.64%	99.17%

Plants that contains it

• Clusia nemorosa
• Hypericum henryi
• Hypericum perforatum

Cross-Links

• PubChem: 162888978
• LOTUS: LTS0208891
• wikiData: Q105182859