(6R)-6-hydroxy-5,7,7-trimethyl-3,4,6,8-tetrahydrocyclopenta[g]isochromen-1-one

Details

• Internal ID: 883031c3-bc5b-4658-946b-4342ff2344a7
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 2-benzopyrans
• IUPAC Name: (6R)-6-hydroxy-5,7,7-trimethyl-3,4,6,8-tetrahydrocyclopenta[g]isochromen-1-one
• SMILES (Canonical): CC1=C2C(C(CC2=CC3=C1CCOC3=O)(C)C)O
• SMILES (Isomeric): CC1=C2[C@@H](C(CC2=CC3=C1CCOC3=O)(C)C)O
• InChI: InChI=1S/C15H18O3/c1-8-10-4-5-18-14(17)11(10)6-9-7-15(2,3)13(16)12(8)9/h6,13,16H,4-5,7H2,1-3H3/t13-/m0/s1
• InChI Key: NHBXPROMQJBCAH-ZDUSSCGKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.32
• H-Bond Acceptor: 3
• 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	+	0.9867	98.67%
Caco-2	+	0.8634	86.34%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8377	83.77%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.9062	90.62%
OATP1B3 inhibitior	+	0.9351	93.51%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.6781	67.81%
P-glycoprotein inhibitior	-	0.8979	89.79%
P-glycoprotein substrate	-	0.8618	86.18%
CYP3A4 substrate	+	0.6085	60.85%
CYP2C9 substrate	-	0.7904	79.04%
CYP2D6 substrate	-	0.8207	82.07%
CYP3A4 inhibition	-	0.8171	81.71%
CYP2C9 inhibition	+	0.5367	53.67%
CYP2C19 inhibition	-	0.7222	72.22%
CYP2D6 inhibition	-	0.9031	90.31%
CYP1A2 inhibition	+	0.6318	63.18%
CYP2C8 inhibition	-	0.8528	85.28%
CYP inhibitory promiscuity	-	0.9162	91.62%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5820	58.20%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.5228	52.28%
Skin irritation	-	0.6610	66.10%
Skin corrosion	-	0.8940	89.40%
Ames mutagenesis	+	0.5463	54.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.6862	68.62%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8055	80.55%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.4653	46.53%
Acute Oral Toxicity (c)	III	0.6035	60.35%
Estrogen receptor binding	+	0.5406	54.06%
Androgen receptor binding	+	0.5480	54.80%
Thyroid receptor binding	+	0.5300	53.00%
Glucocorticoid receptor binding	-	0.5094	50.94%
Aromatase binding	-	0.7156	71.56%
PPAR gamma	+	0.6831	68.31%
Honey bee toxicity	-	0.8883	88.83%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9363	93.63%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.52%	95.56%
CHEMBL2581	P07339	Cathepsin D	95.48%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.48%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	93.42%	91.49%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	92.57%	93.40%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.06%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.05%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.01%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.97%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.47%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.90%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.62%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.60%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.59%	95.89%

Plants that contains it

• Pityrogramma calomelanos

Cross-Links

• PubChem: 162821413
• LOTUS: LTS0165671
• wikiData: Q105179300