(1R,3S)-9-methoxy-1,3-dimethyl-3,4-dihydro-1H-benzo[g]isochromen-10-ol

Details

• Internal ID: f86868f3-3ee3-475b-b1a2-52c5bba0922d
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: (1R,3S)-9-methoxy-1,3-dimethyl-3,4-dihydro-1H-benzo[g]isochromen-10-ol
• InChI: InChI=1S/C16H18O3/c1-9-7-12-8-11-5-4-6-13(18-3)15(11)16(17)14(12)10(2)19-9/h4-6,8-10,17H,7H2,1-3H3/t9-,10+/m0/s1
• InChI Key: XEEVCZPUHQFUAH-VHSXEESVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₈O₃
• Molecular Weight: 258.31 g/mol
• Exact Mass: 258.125594432 g/mol
• Topological Polar Surface Area (TPSA): 38.70 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.58
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9774	97.74%
Caco-2	+	0.8430	84.30%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6148	61.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9078	90.78%
OATP1B3 inhibitior	+	0.9856	98.56%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6392	63.92%
P-glycoprotein inhibitior	-	0.8946	89.46%
P-glycoprotein substrate	-	0.8070	80.70%
CYP3A4 substrate	+	0.5185	51.85%
CYP2C9 substrate	-	0.8074	80.74%
CYP2D6 substrate	+	0.5000	50.00%
CYP3A4 inhibition	-	0.9086	90.86%
CYP2C9 inhibition	-	0.7589	75.89%
CYP2C19 inhibition	+	0.5895	58.95%
CYP2D6 inhibition	-	0.7565	75.65%
CYP1A2 inhibition	+	0.9063	90.63%
CYP2C8 inhibition	-	0.6210	62.10%
CYP inhibitory promiscuity	-	0.6219	62.19%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9013	90.13%
Carcinogenicity (trinary)	Non-required	0.5570	55.70%
Eye corrosion	-	0.9811	98.11%
Eye irritation	-	0.8513	85.13%
Skin irritation	-	0.7785	77.85%
Skin corrosion	-	0.9674	96.74%
Ames mutagenesis	+	0.6963	69.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.6492	64.92%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.6126	61.26%
skin sensitisation	-	0.8619	86.19%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7112	71.12%
Acute Oral Toxicity (c)	III	0.5438	54.38%
Estrogen receptor binding	+	0.7609	76.09%
Androgen receptor binding	-	0.4823	48.23%
Thyroid receptor binding	+	0.5544	55.44%
Glucocorticoid receptor binding	-	0.5713	57.13%
Aromatase binding	+	0.6611	66.11%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9401	94.01%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.7368	73.68%

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	98.27%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.37%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.78%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.42%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.56%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.30%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.89%	95.56%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	88.58%	94.03%
CHEMBL2535	P11166	Glucose transporter	87.18%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.80%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.34%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.48%	95.89%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.41%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	81.14%	94.73%

Plants that contains it

• Karwinskia humboldtiana

Cross-Links

• PubChem: 162930076
• LOTUS: LTS0156751
• wikiData: Q105326313