schweinfurthin F

Details

• Internal ID: 1b30b932-23a7-416d-91b8-aaedd1a99dbb
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthenes
• IUPAC Name: 5-[(E)-2-[(7R,8aR,10aR)-7-hydroxy-4-methoxy-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthen-2-yl]ethenyl]-2-(3-methylbut-2-enyl)benzene-1,3-diol
• SMILES (Canonical): CC(=CCC1=C(C=C(C=C1O)C=CC2=CC3=C(C(=C2)OC)OC4(CCC(C(C4C3)(C)C)O)C)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=C(C=C1O)/C=C/C2=CC3=C(C(=C2)OC)O[C@@]4(CC[C@H](C([C@H]4C3)(C)C)O)C)O)C
• InChI: InChI=1S/C30H38O5/c1-18(2)7-10-22-23(31)14-20(15-24(22)32)9-8-19-13-21-17-26-29(3,4)27(33)11-12-30(26,5)35-28(21)25(16-19)34-6/h7-9,13-16,26-27,31-33H,10-12,17H2,1-6H3/b9-8+/t26-,27-,30-/m1/s1
• InChI Key: BUFNPAYKUGAAAO-HLULBIOLSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₈O₅
• Molecular Weight: 478.60 g/mol
• Exact Mass: 478.27192431 g/mol
• Topological Polar Surface Area (TPSA): 79.20 Ų
• XlogP: 7.00
• Atomic LogP (AlogP): 6.28
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• CHEBI:66436
• 5-{(E)-2-[(2R,4aR,9aR)-2-hydroxy-5-methoxy-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthen-7-yl]ethenyl}-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol
• CHEMBL376007
• SCHEMBL24867153
• Q27134997
• 5-[(E)-2-[(7R,8aR,10aR)-7-hydroxy-4-methoxy-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthen-2-yl]ethenyl]-2-(3-methylbut-2-enyl)benzene-1,3-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9659	96.59%
Caco-2	-	0.6416	64.16%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5812	58.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8695	86.95%
OATP1B3 inhibitior	+	0.9099	90.99%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8064	80.64%
BSEP inhibitior	+	0.9824	98.24%
P-glycoprotein inhibitior	+	0.8222	82.22%
P-glycoprotein substrate	-	0.6093	60.93%
CYP3A4 substrate	+	0.6451	64.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3689	36.89%
CYP3A4 inhibition	-	0.6927	69.27%
CYP2C9 inhibition	-	0.6281	62.81%
CYP2C19 inhibition	+	0.5442	54.42%
CYP2D6 inhibition	-	0.7928	79.28%
CYP1A2 inhibition	+	0.6513	65.13%
CYP2C8 inhibition	+	0.6366	63.66%
CYP inhibitory promiscuity	-	0.6358	63.58%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7420	74.20%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9050	90.50%
Skin irritation	-	0.7277	72.77%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9414	94.14%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8291	82.91%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.7659	76.59%
Acute Oral Toxicity (c)	III	0.3711	37.11%
Estrogen receptor binding	+	0.8095	80.95%
Androgen receptor binding	+	0.7288	72.88%
Thyroid receptor binding	+	0.6897	68.97%
Glucocorticoid receptor binding	+	0.7994	79.94%
Aromatase binding	+	0.7789	77.89%
PPAR gamma	+	0.7844	78.44%
Honey bee toxicity	-	0.7154	71.54%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9879	98.79%

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	99.61%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.81%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.86%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.71%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.03%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.68%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.47%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.12%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.28%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.91%	96.95%
CHEMBL1951	P21397	Monoamine oxidase A	85.82%	91.49%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.57%	91.03%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.56%	93.99%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.54%	92.62%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	84.42%	92.68%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.04%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	83.88%	90.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.09%	95.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.45%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	82.40%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.35%	89.00%
CHEMBL2581	P07339	Cathepsin D	81.97%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.79%	89.62%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.69%	97.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.31%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.03%	97.14%

Plants that contains it

• Macaranga alnifolia

Cross-Links

• PubChem: 16721018
• LOTUS: LTS0203961
• wikiData: Q27134997