(2S)-4,9-dihydroxy-2-(2-hydroxypropan-2-yl)-11-(3-methylbut-2-enyl)-2,3-dihydrofuro[3,2-b]xanthen-5-one

Details

• Internal ID: fa8653c9-3af8-4108-9265-eae8c88cb568
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 4-prenylated xanthones
• IUPAC Name: (2S)-4,9-dihydroxy-2-(2-hydroxypropan-2-yl)-11-(3-methylbut-2-enyl)-2,3-dihydrofuro[3,2-b]xanthen-5-one
• SMILES (Canonical): CC(=CCC1=C2C(=C(C3=C1OC4=C(C3=O)C=CC=C4O)O)CC(O2)C(C)(C)O)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C3=C1OC4=C(C3=O)C=CC=C4O)O)C[C@H](O2)C(C)(C)O)C
• InChI: InChI=1S/C23H24O6/c1-11(2)8-9-13-20-14(10-16(28-20)23(3,4)27)19(26)17-18(25)12-6-5-7-15(24)21(12)29-22(13)17/h5-8,16,24,26-27H,9-10H2,1-4H3/t16-/m0/s1
• InChI Key: ZBFQACWPPVQWER-INIZCTEOSA-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): 96.20 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 3.94
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	-	0.5661	56.61%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8137	81.37%
OATP2B1 inhibitior	-	0.5650	56.50%
OATP1B1 inhibitior	+	0.8843	88.43%
OATP1B3 inhibitior	+	0.9077	90.77%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6482	64.82%
P-glycoprotein inhibitior	+	0.6322	63.22%
P-glycoprotein substrate	-	0.5393	53.93%
CYP3A4 substrate	+	0.6475	64.75%
CYP2C9 substrate	-	0.5948	59.48%
CYP2D6 substrate	-	0.8240	82.40%
CYP3A4 inhibition	-	0.8823	88.23%
CYP2C9 inhibition	+	0.5782	57.82%
CYP2C19 inhibition	+	0.6626	66.26%
CYP2D6 inhibition	-	0.7863	78.63%
CYP1A2 inhibition	-	0.5804	58.04%
CYP2C8 inhibition	+	0.4764	47.64%
CYP inhibitory promiscuity	+	0.6382	63.82%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5776	57.76%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.5298	52.98%
Skin irritation	-	0.7381	73.81%
Skin corrosion	-	0.9374	93.74%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5220	52.20%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.6591	65.91%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8426	84.26%
Acute Oral Toxicity (c)	III	0.4735	47.35%
Estrogen receptor binding	+	0.8395	83.95%
Androgen receptor binding	+	0.6760	67.60%
Thyroid receptor binding	+	0.6097	60.97%
Glucocorticoid receptor binding	+	0.8305	83.05%
Aromatase binding	+	0.6664	66.64%
PPAR gamma	+	0.9235	92.35%
Honey bee toxicity	-	0.7740	77.40%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9861	98.61%

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	99.36%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	97.58%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	97.31%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.06%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.75%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.24%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.99%	89.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.77%	93.99%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	90.35%	89.34%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.76%	95.89%
CHEMBL5103	Q969S8	Histone deacetylase 10	89.01%	90.08%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.50%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.64%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.44%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.15%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.76%	94.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.82%	92.62%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	84.71%	96.37%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.33%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.73%	97.09%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	81.77%	83.10%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.62%	85.30%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.87%	93.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.06%	100.00%

Plants that contains it

• Garcinia mangostana
• Garcinia merguensis
• Morus insignis

Cross-Links

• PubChem: 162987335
• LOTUS: LTS0219342
• wikiData: Q105370563