(1S,9R,12R,13R,15S,16S,17R)-16-hydroxy-1,12-dimethyl-5,10,14-trioxapentacyclo[7.7.1.02,7.012,17.013,15]heptadeca-2,7-diene-4,11-dione

Details

• Internal ID: 4c08a4b7-4e7f-475a-b53c-4aa194926d85
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: (1S,9R,12R,13R,15S,16S,17R)-16-hydroxy-1,12-dimethyl-5,10,14-trioxapentacyclo[7.7.1.02,7.012,17.013,15]heptadeca-2,7-diene-4,11-dione
• SMILES (Canonical): CC12C3C(C=C4C1=CC(=O)OC4)OC(=O)C3(C5C(C2O)O5)C
• SMILES (Isomeric): C[C@]12[C@H]3[C@@H](C=C4C1=CC(=O)OC4)OC(=O)[C@]3([C@@H]5[C@H]([C@H]2O)O5)C
• InChI: InChI=1S/C16H16O6/c1-15-7-4-9(17)20-5-6(7)3-8-11(15)16(2,14(19)21-8)13-10(22-13)12(15)18/h3-4,8,10-13,18H,5H2,1-2H3/t8-,10+,11-,12-,13+,15-,16-/m1/s1
• InChI Key: MJENRSWOSGZXHW-IPWFQQAISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₆O₆
• Molecular Weight: 304.29 g/mol
• Exact Mass: 304.09468823 g/mol
• Topological Polar Surface Area (TPSA): 85.40 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 0.11
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9758	97.58%
Caco-2	-	0.5880	58.80%
Blood Brain Barrier	+	0.5839	58.39%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7791	77.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9002	90.02%
OATP1B3 inhibitior	+	0.9555	95.55%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8239	82.39%
P-glycoprotein inhibitior	-	0.8028	80.28%
P-glycoprotein substrate	-	0.6640	66.40%
CYP3A4 substrate	+	0.5872	58.72%
CYP2C9 substrate	-	0.7958	79.58%
CYP2D6 substrate	-	0.8837	88.37%
CYP3A4 inhibition	-	0.7713	77.13%
CYP2C9 inhibition	-	0.8403	84.03%
CYP2C19 inhibition	-	0.8546	85.46%
CYP2D6 inhibition	-	0.9276	92.76%
CYP1A2 inhibition	-	0.8349	83.49%
CYP2C8 inhibition	-	0.8902	89.02%
CYP inhibitory promiscuity	-	0.8129	81.29%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4688	46.88%
Eye corrosion	-	0.9787	97.87%
Eye irritation	-	0.9540	95.40%
Skin irritation	-	0.6083	60.83%
Skin corrosion	-	0.8890	88.90%
Ames mutagenesis	+	0.5763	57.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.8974	89.74%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.7251	72.51%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.6900	69.00%
Acute Oral Toxicity (c)	I	0.3723	37.23%
Estrogen receptor binding	+	0.7305	73.05%
Androgen receptor binding	+	0.5434	54.34%
Thyroid receptor binding	-	0.6490	64.90%
Glucocorticoid receptor binding	+	0.6108	61.08%
Aromatase binding	+	0.5993	59.93%
PPAR gamma	+	0.6361	63.61%
Honey bee toxicity	-	0.7876	78.76%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9186	91.86%

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	93.14%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.97%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	91.05%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.00%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.54%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.72%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.22%	85.14%
CHEMBL2581	P07339	Cathepsin D	85.36%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.61%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.43%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.13%	97.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 70695738
• LOTUS: LTS0003227
• wikiData: Q105165369