(1R,2R,5S,7S,9S,17R)-11,14-dihydroxy-12-methoxy-17-methyl-6,8-dioxapentacyclo[7.7.1.02,7.05,17.010,15]heptadeca-10(15),11,13-trien-16-one

Details

• Internal ID: 1d917ad8-9a45-4662-a2c1-2384a47ef0fc
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
• IUPAC Name: (1R,2R,5S,7S,9S,17R)-11,14-dihydroxy-12-methoxy-17-methyl-6,8-dioxapentacyclo[7.7.1.02,7.05,17.010,15]heptadeca-10(15),11,13-trien-16-one
• SMILES (Canonical): CC12C3CCC4C1C(=O)C5=C(C2OC4O3)C(=C(C=C5O)OC)O
• SMILES (Isomeric): C[C@]12[C@@H]3CC[C@@H]4[C@H]1C(=O)C5=C([C@H]2O[C@@H]4O3)C(=C(C=C5O)OC)O
• InChI: InChI=1S/C17H18O6/c1-17-9-4-3-6-12(17)14(20)10-7(18)5-8(21-2)13(19)11(10)15(17)23-16(6)22-9/h5-6,9,12,15-16,18-19H,3-4H2,1-2H3/t6-,9+,12+,15-,16+,17+/m1/s1
• InChI Key: OTRFGWOUMRJFGT-CJHXGYTJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₆
• Molecular Weight: 318.32 g/mol
• Exact Mass: 318.11033829 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.13
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9399	93.99%
Caco-2	+	0.5121	51.21%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7675	76.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8592	85.92%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8309	83.09%
P-glycoprotein inhibitior	-	0.7425	74.25%
P-glycoprotein substrate	-	0.7501	75.01%
CYP3A4 substrate	+	0.6455	64.55%
CYP2C9 substrate	-	0.6021	60.21%
CYP2D6 substrate	-	0.8232	82.32%
CYP3A4 inhibition	-	0.9007	90.07%
CYP2C9 inhibition	-	0.9476	94.76%
CYP2C19 inhibition	-	0.8834	88.34%
CYP2D6 inhibition	-	0.8932	89.32%
CYP1A2 inhibition	-	0.6108	61.08%
CYP2C8 inhibition	-	0.5996	59.96%
CYP inhibitory promiscuity	-	0.8954	89.54%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5825	58.25%
Eye corrosion	-	0.9853	98.53%
Eye irritation	-	0.6389	63.89%
Skin irritation	-	0.6493	64.93%
Skin corrosion	-	0.8973	89.73%
Ames mutagenesis	-	0.5837	58.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5976	59.76%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8596	85.96%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.4836	48.36%
Acute Oral Toxicity (c)	III	0.6432	64.32%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.7111	71.11%
Thyroid receptor binding	+	0.5227	52.27%
Glucocorticoid receptor binding	+	0.8192	81.92%
Aromatase binding	+	0.5638	56.38%
PPAR gamma	+	0.8333	83.33%
Honey bee toxicity	-	0.8229	82.29%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5051	50.51%
Fish aquatic toxicity	+	0.7216	72.16%

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	99.71%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	97.10%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.69%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	94.39%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.27%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.50%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.17%	94.45%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	87.98%	91.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.85%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.66%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.50%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.39%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.47%	92.62%
CHEMBL2581	P07339	Cathepsin D	84.61%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.15%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.09%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.90%	99.23%
CHEMBL4355	O14976	Serine/threonine-protein kinase GAK	82.43%	89.32%
CHEMBL4530	P00488	Coagulation factor XIII	82.03%	96.00%
CHEMBL1937	Q92769	Histone deacetylase 2	81.86%	94.75%
CHEMBL4208	P20618	Proteasome component C5	81.51%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.57%	100.00%

Plants that contains it

• Cordia oncocalyx

Cross-Links

• PubChem: 101683238
• LOTUS: LTS0056230
• wikiData: Q105199768