10H-Cyclopenta[h]pyrano[3,2-b]xanthene-3-carboxylic acid, 1,2,3,6-tetrahydro-12-(3-hydroperoxy-3-methyl-1-butenyl)-3,7-dihydroxy-10,10-dimethyl-4-(1-methylethenyl)-1,6-dioxo-, methyl ester

Details

• Internal ID: 7e87d528-a519-408b-b7a9-e3e88cce25bd
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > Pyranoxanthones
• IUPAC Name: methyl 21-(3-hydroperoxy-3-methylbut-1-enyl)-7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-prop-1-en-2-yl-2,19-dioxapentacyclo[11.8.0.03,11.04,8.015,20]henicosa-1(13),3,8,10,14,16,20-heptaene-7-carboxylate
• SMILES (Canonical): CC(=C)C1=C2C(=C3C(=C1)C(=O)C4=C(O3)C(=C5C(=C4O)C=CC(O5)(C)C)C=CC(C)(C)OO)C(=O)CC2(C(=O)OC)O
• SMILES (Isomeric): CC(=C)C1=C2C(=C3C(=C1)C(=O)C4=C(O3)C(=C5C(=C4O)C=CC(O5)(C)C)C=CC(C)(C)OO)C(=O)CC2(C(=O)OC)O
• InChI: InChI=1S/C31H30O10/c1-14(2)17-12-18-24(34)21-23(33)15-8-10-29(3,4)40-25(15)16(9-11-30(5,6)41-37)26(21)39-27(18)20-19(32)13-31(36,22(17)20)28(35)38-7/h8-12,33,36-37H,1,13H2,2-7H3
• InChI Key: DHSZUELPJXKISQ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₀O₁₀
• Molecular Weight: 562.60 g/mol
• Exact Mass: 562.18389715 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 5.10
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 10H-Cyclopenta[h]pyrano[3,2-b]xanthene-3-carboxylic acid, 1,2,3,6-tetrahydro-12-(3-hydroperoxy-3-methyl-1-butenyl)-3,7-dihydroxy-10,10-dimethyl-4-(1-methylethenyl)-1,6-dioxo-, methyl ester
• 161017-01-2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9578	95.78%
Caco-2	-	0.7889	78.89%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6306	63.06%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.8397	83.97%
OATP1B3 inhibitior	+	0.8953	89.53%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9199	91.99%
P-glycoprotein inhibitior	+	0.7688	76.88%
P-glycoprotein substrate	+	0.7181	71.81%
CYP3A4 substrate	+	0.7076	70.76%
CYP2C9 substrate	+	0.6237	62.37%
CYP2D6 substrate	-	0.8610	86.10%
CYP3A4 inhibition	+	0.5603	56.03%
CYP2C9 inhibition	-	0.6960	69.60%
CYP2C19 inhibition	-	0.6159	61.59%
CYP2D6 inhibition	-	0.8351	83.51%
CYP1A2 inhibition	-	0.7151	71.51%
CYP2C8 inhibition	+	0.7064	70.64%
CYP inhibitory promiscuity	-	0.6905	69.05%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.4393	43.93%
Eye corrosion	-	0.9811	98.11%
Eye irritation	-	0.8498	84.98%
Skin irritation	-	0.7676	76.76%
Skin corrosion	-	0.9304	93.04%
Ames mutagenesis	+	0.6746	67.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7281	72.81%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.5801	58.01%
skin sensitisation	-	0.7088	70.88%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6167	61.67%
Acute Oral Toxicity (c)	III	0.4822	48.22%
Estrogen receptor binding	+	0.8281	82.81%
Androgen receptor binding	+	0.7387	73.87%
Thyroid receptor binding	+	0.6623	66.23%
Glucocorticoid receptor binding	+	0.7717	77.17%
Aromatase binding	+	0.7512	75.12%
PPAR gamma	+	0.7079	70.79%
Honey bee toxicity	-	0.6411	64.11%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9773	97.73%

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	99.94%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.72%	94.45%
CHEMBL2581	P07339	Cathepsin D	98.37%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.18%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	94.68%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.12%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.70%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.49%	95.56%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	91.46%	94.42%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	90.04%	80.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.21%	99.23%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	88.95%	85.30%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	88.24%	90.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.29%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.22%	95.89%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.07%	89.34%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.22%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	85.88%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	85.19%	91.49%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	85.00%	92.29%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.06%	91.07%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	84.03%	92.88%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.27%	91.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.03%	96.09%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.64%	89.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.32%	97.14%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.28%	96.90%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.47%	95.71%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.87%	100.00%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	80.37%	81.14%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.31%	83.10%

Plants that contains it

• Artocarpus heterophyllus

Cross-Links

• PubChem: 162927899
• LOTUS: LTS0172440
• wikiData: Q104980826