4-[(12S,14S,15R)-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-1,2-diol

Details

• Internal ID: 55b8658b-60cb-4a46-a0ac-b69159f6f765
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > 2,2-dimethyl-1-benzopyrans
• IUPAC Name: 4-[(12S,14S,15R)-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-1,2-diol
• SMILES (Canonical): CC1(C=CC2=C3C4C(CC3=C(C=C2O1)OC)C(C4C5=CC(=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=CC(=C(C=C5)O)O)(C)C)C
• InChI: InChI=1S/C25H28O4/c1-24(2)9-8-14-20(29-24)12-19(28-5)15-11-16-22(21(14)15)23(25(16,3)4)13-6-7-17(26)18(27)10-13/h6-10,12,16,22-23,26-27H,11H2,1-5H3/t16-,22-,23-/m0/s1
• InChI Key: SXWKVOUWXXHZAC-GMWOSMDTSA-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	+	0.9741	97.41%
Caco-2	+	0.6237	62.37%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5872	58.72%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.9195	91.95%
OATP1B3 inhibitior	+	0.9558	95.58%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6121	61.21%
P-glycoprotein inhibitior	-	0.4658	46.58%
P-glycoprotein substrate	-	0.5861	58.61%
CYP3A4 substrate	+	0.6444	64.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6790	67.90%
CYP3A4 inhibition	+	0.5129	51.29%
CYP2C9 inhibition	-	0.6790	67.90%
CYP2C19 inhibition	+	0.7154	71.54%
CYP2D6 inhibition	-	0.8467	84.67%
CYP1A2 inhibition	-	0.6010	60.10%
CYP2C8 inhibition	+	0.7082	70.82%
CYP inhibitory promiscuity	+	0.5727	57.27%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4982	49.82%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.8132	81.32%
Skin irritation	-	0.7522	75.22%
Skin corrosion	-	0.9170	91.70%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7112	71.12%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.6936	69.36%
skin sensitisation	-	0.8359	83.59%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.5577	55.77%
Acute Oral Toxicity (c)	III	0.5088	50.88%
Estrogen receptor binding	+	0.9230	92.30%
Androgen receptor binding	+	0.6943	69.43%
Thyroid receptor binding	+	0.8390	83.90%
Glucocorticoid receptor binding	+	0.8136	81.36%
Aromatase binding	+	0.7422	74.22%
PPAR gamma	+	0.7721	77.21%
Honey bee toxicity	-	0.7375	73.75%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6251	62.51%
Fish aquatic toxicity	+	0.9846	98.46%

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	99.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.18%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	97.71%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.38%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.29%	95.89%
CHEMBL4208	P20618	Proteasome component C5	90.64%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.20%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.80%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.94%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.54%	86.33%
CHEMBL3438	Q05513	Protein kinase C zeta	87.33%	88.48%
CHEMBL2535	P11166	Glucose transporter	86.61%	98.75%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	86.58%	91.03%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.30%	92.94%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.10%	89.62%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.09%	92.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.46%	85.14%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.47%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.45%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	80.91%	91.19%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.30%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.06%	90.71%

Plants that contains it

• Artocarpus chama

Cross-Links

• PubChem: 16080289
• LOTUS: LTS0169675
• wikiData: Q105263372