(15S)-11,19-dihydroxy-7,7-dimethyl-15-(2-methylprop-1-enyl)-2,8,16-trioxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4(9),5,10,17(22),18,20-octaen-13-one

Details

• Internal ID: d4cf5ef3-9368-46ed-8625-1354ddebd361
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Pyranoflavonoids
• IUPAC Name: (15S)-11,19-dihydroxy-7,7-dimethyl-15-(2-methylprop-1-enyl)-2,8,16-trioxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4(9),5,10,17(22),18,20-octaen-13-one
• SMILES (Canonical): CC(=CC1C2=C(C3=C(O1)C=C(C=C3)O)OC4=C(C2=O)C(=CC5=C4C=CC(O5)(C)C)O)C
• SMILES (Isomeric): CC(=C[C@H]1C2=C(C3=C(O1)C=C(C=C3)O)OC4=C(C2=O)C(=CC5=C4C=CC(O5)(C)C)O)C
• InChI: InChI=1S/C25H22O6/c1-12(2)9-19-21-22(28)20-16(27)11-18-15(7-8-25(3,4)31-18)23(20)30-24(21)14-6-5-13(26)10-17(14)29-19/h5-11,19,26-27H,1-4H3/t19-/m0/s1
• InChI Key: GDQXJMLXEYSICD-IBGZPJMESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₂O₆
• Molecular Weight: 418.40 g/mol
• Exact Mass: 418.14163842 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.46
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• BDBM50291299

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9912	99.12%
Caco-2	-	0.5293	52.93%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8195	81.95%
OATP2B1 inhibitior	-	0.7129	71.29%
OATP1B1 inhibitior	+	0.8459	84.59%
OATP1B3 inhibitior	+	0.9725	97.25%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8383	83.83%
P-glycoprotein inhibitior	+	0.7787	77.87%
P-glycoprotein substrate	+	0.6258	62.58%
CYP3A4 substrate	+	0.6638	66.38%
CYP2C9 substrate	-	0.6192	61.92%
CYP2D6 substrate	-	0.8382	83.82%
CYP3A4 inhibition	-	0.6074	60.74%
CYP2C9 inhibition	+	0.7876	78.76%
CYP2C19 inhibition	+	0.7874	78.74%
CYP2D6 inhibition	-	0.7827	78.27%
CYP1A2 inhibition	+	0.5852	58.52%
CYP2C8 inhibition	+	0.5163	51.63%
CYP inhibitory promiscuity	+	0.7852	78.52%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.5418	54.18%
Eye corrosion	-	0.9900	99.00%
Eye irritation	+	0.5587	55.87%
Skin irritation	-	0.6965	69.65%
Skin corrosion	-	0.9655	96.55%
Ames mutagenesis	+	0.6063	60.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5787	57.87%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	-	0.6073	60.73%
skin sensitisation	-	0.6656	66.56%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5579	55.79%
Acute Oral Toxicity (c)	III	0.7408	74.08%
Estrogen receptor binding	+	0.8648	86.48%
Androgen receptor binding	+	0.8055	80.55%
Thyroid receptor binding	+	0.7544	75.44%
Glucocorticoid receptor binding	+	0.9003	90.03%
Aromatase binding	+	0.6731	67.31%
PPAR gamma	+	0.7950	79.50%
Honey bee toxicity	-	0.6364	63.64%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9767	97.67%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4409	Q9Y233	Phosphodiesterase 10A	510 nM	IC50	via Super-PRED
CHEMBL4425	Q01064	Phosphodiesterase 1B	300 nM	IC50	via Super-PRED
CHEMBL2652	O00408	Phosphodiesterase 2A	590 nM	IC50	via Super-PRED
CHEMBL288	Q08499	Phosphodiesterase 4D	5.4 nM; 250 nM	IC50; IC50	via Super-PRED; via Super-PRED
CHEMBL1827	O76074	Phosphodiesterase 5A	410 nM	IC50	via Super-PRED
CHEMBL3535	O76083	Phosphodiesterase 9A	350 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.43%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.92%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	95.74%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.39%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.36%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.09%	94.45%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	86.70%	93.10%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	86.30%	90.93%
CHEMBL3401	O75469	Pregnane X receptor	85.91%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.41%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.19%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.29%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.07%	95.89%
CHEMBL3194	P02766	Transthyretin	81.79%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.77%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.02%	100.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	80.87%	91.38%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.28%	96.09%
CHEMBL242	Q92731	Estrogen receptor beta	80.14%	98.35%

Plants that contains it

• Artocarpus altilis
• Artocarpus elasticus
• Artocarpus heterophyllus
• Morus alba

Cross-Links

• PubChem: 92471957
• LOTUS: LTS0015686
• wikiData: Q105006889