4-[(12R,14R,15S)-9-methoxy-5,5,13,13-tetramethyl-6-oxatetracyclo[8.5.0.02,7.012,15]pentadeca-1,3,7,9-tetraen-14-yl]benzene-1,3-diol

Details

• Internal ID: a7e2f562-b387-4412-a4a4-0e233727fe67
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > 2,2-dimethyl-1-benzopyrans
• IUPAC Name: 4-[(12R,14R,15S)-9-methoxy-5,5,13,13-tetramethyl-6-oxatetracyclo[8.5.0.02,7.012,15]pentadeca-1,3,7,9-tetraen-14-yl]benzene-1,3-diol
• SMILES (Canonical): CC1(C=CC2=C3C4C(CC3=C(C=C2O1)OC)C(C4C5=C(C=C(C=C5)O)O)(C)C)C
• SMILES (Isomeric): CC1(C=CC2=C3[C@H]4[C@@H](CC3=C(C=C2O1)OC)C([C@@H]4C5=C(C=C(C=C5)O)O)(C)C)C
• InChI: InChI=1S/C25H28O4/c1-24(2)9-8-15-20(29-24)12-19(28-5)16-11-17-22(21(15)16)23(25(17,3)4)14-7-6-13(26)10-18(14)27/h6-10,12,17,22-23,26-27H,11H2,1-5H3/t17-,22-,23-/m1/s1
• InChI Key: GYUGGYHLTJWEBQ-NLSFWIRASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₄
• Molecular Weight: 392.50 g/mol
• Exact Mass: 392.19875937 g/mol
• Topological Polar Surface Area (TPSA): 58.90 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.37
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9779	97.79%
Caco-2	+	0.6557	65.57%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5459	54.59%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.8936	89.36%
OATP1B3 inhibitior	+	0.9266	92.66%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7489	74.89%
P-glycoprotein inhibitior	-	0.4873	48.73%
P-glycoprotein substrate	+	0.7077	70.77%
CYP3A4 substrate	+	0.6761	67.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3557	35.57%
CYP3A4 inhibition	+	0.6964	69.64%
CYP2C9 inhibition	+	0.5569	55.69%
CYP2C19 inhibition	+	0.7489	74.89%
CYP2D6 inhibition	-	0.7887	78.87%
CYP1A2 inhibition	+	0.6047	60.47%
CYP2C8 inhibition	+	0.7270	72.70%
CYP inhibitory promiscuity	+	0.8274	82.74%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4972	49.72%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.8161	81.61%
Skin irritation	-	0.7606	76.06%
Skin corrosion	-	0.9230	92.30%
Ames mutagenesis	+	0.5263	52.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.6803	68.03%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.6436	64.36%
skin sensitisation	-	0.8499	84.99%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.5949	59.49%
Acute Oral Toxicity (c)	III	0.5152	51.52%
Estrogen receptor binding	+	0.8721	87.21%
Androgen receptor binding	+	0.7156	71.56%
Thyroid receptor binding	+	0.8347	83.47%
Glucocorticoid receptor binding	+	0.7754	77.54%
Aromatase binding	+	0.7282	72.82%
PPAR gamma	+	0.8162	81.62%
Honey bee toxicity	-	0.7514	75.14%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9834	98.34%

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	98.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.25%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.25%	94.45%
CHEMBL2535	P11166	Glucose transporter	92.39%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.30%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.03%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.49%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.08%	89.62%
CHEMBL2581	P07339	Cathepsin D	87.73%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.26%	95.56%
CHEMBL4208	P20618	Proteasome component C5	86.96%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.12%	99.17%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	86.01%	91.79%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.49%	99.15%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.48%	92.94%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.96%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.87%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.63%	97.14%
CHEMBL3085	P43003	Excitatory amino acid transporter 1	82.48%	94.67%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	82.35%	85.49%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.13%	92.62%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.02%	91.03%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.85%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.84%	97.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.82%	93.40%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.67%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.28%	89.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.12%	91.19%

Plants that contains it

• Morus cathayana

Cross-Links

• PubChem: 163188123
• LOTUS: LTS0101103
• wikiData: Q105024182