(13R)-8,17,19-trihydroxy-6-methoxy-14,14-dimethyl-3,15-dioxapentacyclo[11.6.1.02,11.04,9.016,20]icosa-1(20),2(11),4,6,8,16,18-heptaen-10-one

Details

• Internal ID: abf519fe-3a28-4182-acc3-40f03640ef3b
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: (13R)-8,17,19-trihydroxy-6-methoxy-14,14-dimethyl-3,15-dioxapentacyclo[11.6.1.02,11.04,9.016,20]icosa-1(20),2(11),4,6,8,16,18-heptaen-10-one
• SMILES (Canonical): CC1(C2CC3=C(C4=C2C(=C(C=C4O)O)O1)OC5=CC(=CC(=C5C3=O)O)OC)C
• SMILES (Isomeric): CC1([C@@H]2CC3=C(C4=C2C(=C(C=C4O)O)O1)OC5=CC(=CC(=C5C3=O)O)OC)C
• InChI: InChI=1S/C21H18O7/c1-21(2)10-6-9-18(25)16-11(22)4-8(26-3)5-14(16)27-19(9)17-12(23)7-13(24)20(28-21)15(10)17/h4-5,7,10,22-24H,6H2,1-3H3/t10-/m1/s1
• InChI Key: NMKFZSNRHNHWLX-SNVBAGLBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₈O₇
• Molecular Weight: 382.40 g/mol
• Exact Mass: 382.10525291 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.40
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9738	97.38%
Caco-2	+	0.5201	52.01%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6857	68.57%
OATP2B1 inhibitior	-	0.6971	69.71%
OATP1B1 inhibitior	+	0.8526	85.26%
OATP1B3 inhibitior	+	0.9356	93.56%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6007	60.07%
P-glycoprotein inhibitior	-	0.4919	49.19%
P-glycoprotein substrate	-	0.6513	65.13%
CYP3A4 substrate	+	0.6477	64.77%
CYP2C9 substrate	-	0.5598	55.98%
CYP2D6 substrate	-	0.8049	80.49%
CYP3A4 inhibition	-	0.5501	55.01%
CYP2C9 inhibition	-	0.6990	69.90%
CYP2C19 inhibition	+	0.5479	54.79%
CYP2D6 inhibition	+	0.5170	51.70%
CYP1A2 inhibition	+	0.6187	61.87%
CYP2C8 inhibition	+	0.6272	62.72%
CYP inhibitory promiscuity	+	0.6009	60.09%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4928	49.28%
Eye corrosion	-	0.9861	98.61%
Eye irritation	+	0.6589	65.89%
Skin irritation	-	0.7669	76.69%
Skin corrosion	-	0.9502	95.02%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6837	68.37%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8305	83.05%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6895	68.95%
Acute Oral Toxicity (c)	III	0.6461	64.61%
Estrogen receptor binding	+	0.8937	89.37%
Androgen receptor binding	+	0.7838	78.38%
Thyroid receptor binding	+	0.5513	55.13%
Glucocorticoid receptor binding	+	0.8770	87.70%
Aromatase binding	+	0.6107	61.07%
PPAR gamma	+	0.7989	79.89%
Honey bee toxicity	-	0.7940	79.40%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9037	90.37%

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	99.75%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.32%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.49%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.09%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.68%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.34%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.27%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	91.81%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.86%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.65%	98.95%
CHEMBL4208	P20618	Proteasome component C5	87.91%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.26%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.06%	99.15%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.90%	96.77%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.86%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.66%	95.89%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	83.10%	85.11%
CHEMBL340	P08684	Cytochrome P450 3A4	81.61%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.50%	92.94%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.49%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.79%	92.62%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	80.50%	80.00%

Plants that contains it

• Artocarpus altilis
• Artocarpus heterophyllus

Cross-Links

• PubChem: 163036529
• LOTUS: LTS0240035
• wikiData: Q105181823