(1R,2S,9R,10S,12R)-2-hydroxy-4,9-dimethyl-13-methylidene-6-oxatetracyclo[7.4.0.03,7.010,12]trideca-3,7-dien-5-one

Details

• Internal ID: 0b3766b0-9c14-4b19-90af-169e6033d247
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (1R,2S,9R,10S,12R)-2-hydroxy-4,9-dimethyl-13-methylidene-6-oxatetracyclo[7.4.0.03,7.010,12]trideca-3,7-dien-5-one
• SMILES (Canonical): CC1=C2C(C3C(=C)C4CC4C3(C=C2OC1=O)C)O
• SMILES (Isomeric): CC1=C2[C@H]([C@@H]3C(=C)[C@@H]4C[C@@H]4[C@]3(C=C2OC1=O)C)O
• InChI: InChI=1S/C15H16O3/c1-6-8-4-9(8)15(3)5-10-11(13(16)12(6)15)7(2)14(17)18-10/h5,8-9,12-13,16H,1,4H2,2-3H3/t8-,9-,12-,13+,15+/m0/s1
• InChI Key: BMSHIMSHONQYAQ-WLGFQKAXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₃
• Molecular Weight: 244.28 g/mol
• Exact Mass: 244.109944368 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.95
• 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	+	0.9973	99.73%
Caco-2	+	0.5245	52.45%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5656	56.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8494	84.94%
OATP1B3 inhibitior	+	0.9448	94.48%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8805	88.05%
P-glycoprotein inhibitior	-	0.8700	87.00%
P-glycoprotein substrate	-	0.8693	86.93%
CYP3A4 substrate	+	0.6233	62.33%
CYP2C9 substrate	-	0.7919	79.19%
CYP2D6 substrate	-	0.8698	86.98%
CYP3A4 inhibition	-	0.6922	69.22%
CYP2C9 inhibition	-	0.8898	88.98%
CYP2C19 inhibition	-	0.8099	80.99%
CYP2D6 inhibition	-	0.9332	93.32%
CYP1A2 inhibition	+	0.5263	52.63%
CYP2C8 inhibition	-	0.7599	75.99%
CYP inhibitory promiscuity	-	0.5936	59.36%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4097	40.97%
Eye corrosion	-	0.9571	95.71%
Eye irritation	-	0.8579	85.79%
Skin irritation	+	0.5335	53.35%
Skin corrosion	-	0.8772	87.72%
Ames mutagenesis	-	0.6028	60.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.5701	57.01%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	+	0.4892	48.92%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5196	51.96%
Acute Oral Toxicity (c)	III	0.4052	40.52%
Estrogen receptor binding	+	0.7611	76.11%
Androgen receptor binding	+	0.6661	66.61%
Thyroid receptor binding	-	0.5502	55.02%
Glucocorticoid receptor binding	+	0.5481	54.81%
Aromatase binding	-	0.6273	62.73%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8417	84.17%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9860	98.60%

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	91.95%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	91.34%	90.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.32%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.38%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.87%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.87%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.48%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.91%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.00%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	84.54%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.52%	96.61%
CHEMBL4530	P00488	Coagulation factor XIII	81.68%	96.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 122182497
• LOTUS: LTS0175664
• wikiData: Q104938533