(3S)-3,5,9-trihydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-enyl)-3,4-dihydropyrano[3,2-b]xanthen-6-one

Details

• Internal ID: 48e11489-f054-4463-a34a-443b3cd7ea4f
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 8-prenylated xanthones
• IUPAC Name: (3S)-3,5,9-trihydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-enyl)-3,4-dihydropyrano[3,2-b]xanthen-6-one
• SMILES (Canonical): CC(=CCC1=C(C(=CC2=C1C(=O)C3=C(C4=C(C=C3O2)OC(C(C4)O)(C)C)O)O)OC)C
• SMILES (Isomeric): CC(=CCC1=C(C(=CC2=C1C(=O)C3=C(C4=C(C=C3O2)OC([C@H](C4)O)(C)C)O)O)OC)C
• InChI: InChI=1S/C24H26O7/c1-11(2)6-7-12-19-16(9-14(25)23(12)29-5)30-17-10-15-13(21(27)20(17)22(19)28)8-18(26)24(3,4)31-15/h6,9-10,18,25-27H,7-8H2,1-5H3/t18-/m0/s1
• InChI Key: KCMPFWGUVNEDHW-SFHVURJKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₆O₇
• Molecular Weight: 426.50 g/mol
• Exact Mass: 426.16785316 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 3.95
• H-Bond Acceptor: 7
• 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	+	0.9852	98.52%
Caco-2	+	0.5802	58.02%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5533	55.33%
OATP2B1 inhibitior	-	0.7118	71.18%
OATP1B1 inhibitior	+	0.9005	90.05%
OATP1B3 inhibitior	+	0.9148	91.48%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8148	81.48%
P-glycoprotein inhibitior	+	0.6138	61.38%
P-glycoprotein substrate	-	0.6102	61.02%
CYP3A4 substrate	+	0.6404	64.04%
CYP2C9 substrate	-	0.5948	59.48%
CYP2D6 substrate	-	0.7986	79.86%
CYP3A4 inhibition	-	0.8572	85.72%
CYP2C9 inhibition	-	0.5126	51.26%
CYP2C19 inhibition	+	0.6272	62.72%
CYP2D6 inhibition	-	0.6283	62.83%
CYP1A2 inhibition	+	0.5274	52.74%
CYP2C8 inhibition	+	0.6064	60.64%
CYP inhibitory promiscuity	-	0.5193	51.93%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6144	61.44%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.7655	76.55%
Skin irritation	-	0.7354	73.54%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4201	42.01%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.5822	58.22%
skin sensitisation	-	0.7647	76.47%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.8608	86.08%
Acute Oral Toxicity (c)	III	0.5232	52.32%
Estrogen receptor binding	+	0.9061	90.61%
Androgen receptor binding	+	0.6295	62.95%
Thyroid receptor binding	+	0.5904	59.04%
Glucocorticoid receptor binding	+	0.8610	86.10%
Aromatase binding	+	0.7426	74.26%
PPAR gamma	+	0.8475	84.75%
Honey bee toxicity	-	0.6221	62.21%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9571	95.71%

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	99.86%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.01%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.82%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.06%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.46%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.92%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	89.82%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.67%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.51%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.36%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.75%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.04%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	84.39%	94.75%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.12%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.02%	99.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.75%	89.34%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.39%	85.30%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.65%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.25%	99.23%

Plants that contains it

• Aster bellidiastrum
• Caragana halodendron
• Davallia divaricata
• Dolomiaea souliei
• Eucalyptus camaldulensis
• Garcinia mangostana
• Ligularia vellerea
• Lonicera hypoleuca
• Nicotiana sylvestris
• Serpocaulon triseriale

Cross-Links

• PubChem: 92448128
• NPASS: NPC256364
• LOTUS: LTS0056527
• wikiData: Q105138835