Rocaglaol

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	5a83a9be-171d-45fe-ad1c-d5f7e2deec26
Taxonomy	Organoheterocyclic compounds > Benzofurans > Flavaglines
IUPAC Name	(1R,3S,3aR,8bS)-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1,8b-diol
SMILES (Canonical)	COC1=CC=C(C=C1)C23C(CC(C2(C4=C(O3)C=C(C=C4OC)OC)O)O)C5=CC=CC=C5
SMILES (Isomeric)	COC1=CC=C(C=C1)[C@]23[C@@H](C[C@H]([C@]2(C4=C(O3)C=C(C=C4OC)OC)O)O)C5=CC=CC=C5
InChI	InChI=1S/C26H26O6/c1-29-18-11-9-17(10-12-18)26-20(16-7-5-4-6-8-16)15-23(27)25(26,28)24-21(31-3)13-19(30-2)14-22(24)32-26/h4-14,20,23,27-28H,15H2,1-3H3/t20-,23+,25+,26-/m0/s1
InChI Key	RRVZOJQBRVGMMK-HCBGRYSISA-N
Popularity	22 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₆H₂₆O₆
Molecular Weight	434.50 g/mol
Exact Mass	434.17293854 g/mol
Topological Polar Surface Area (TPSA)	77.40 Å²
XlogP	3.20
Atomic LogP (AlogP)	3.74
H-Bond Acceptor	6
H-Bond Donor	2
Rotatable Bonds	5

Synonyms

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147059-46-9

(1R,3S,3aR,8bS)-6,8-Dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1,8b-diol

(1R,3S,3aR,8bS)-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1,8b-diol

Ferrugin

(+/-)-Rocaglaol

SCHEMBL750024

CHEMBL468454

HY-N1342

NSC695796

CCG-261725

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9724	97.24%
Caco-2	+	0.5676	56.76%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6618	66.18%
OATP2B1 inhibitior	-	0.8614	86.14%
OATP1B1 inhibitior	+	0.8955	89.55%
OATP1B3 inhibitior	+	0.9499	94.99%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8655	86.55%
P-glycoprotein inhibitior	+	0.7790	77.90%
P-glycoprotein substrate	-	0.6396	63.96%
CYP3A4 substrate	+	0.6174	61.74%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	+	0.4780	47.80%
CYP3A4 inhibition	-	0.7471	74.71%
CYP2C9 inhibition	-	0.8198	81.98%
CYP2C19 inhibition	-	0.6508	65.08%
CYP2D6 inhibition	-	0.8483	84.83%
CYP1A2 inhibition	-	0.7076	70.76%
CYP2C8 inhibition	+	0.6884	68.84%
CYP inhibitory promiscuity	-	0.6230	62.30%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.3572	35.72%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.8329	83.29%
Skin irritation	-	0.7762	77.62%
Skin corrosion	-	0.9283	92.83%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7126	71.26%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8775	87.75%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6177	61.77%
Acute Oral Toxicity (c)	III	0.4677	46.77%
Estrogen receptor binding	+	0.7865	78.65%
Androgen receptor binding	+	0.7993	79.93%
Thyroid receptor binding	+	0.7576	75.76%
Glucocorticoid receptor binding	+	0.7320	73.20%
Aromatase binding	-	0.5059	50.59%
PPAR gamma	+	0.7001	70.01%
Honey bee toxicity	-	0.8710	87.10%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6551	65.51%
Fish aquatic toxicity	+	0.8823	88.23%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5533	Q04206	Nuclear factor NF-kappa-B p65 subunit	0.005 nM	ED50	PMID: 23301897

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.20%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.11%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.25%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.98%	97.09%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	92.68%	89.44%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.94%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.38%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	89.93%	90.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.13%	97.14%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	89.11%	94.08%
CHEMBL4208	P20618	Proteasome component C5	89.07%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.43%	92.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.24%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.22%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.38%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.63%	94.00%
CHEMBL240	Q12809	HERG	83.19%	89.76%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.91%	96.00%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.84%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.73%	96.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.76%	91.07%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.09%	94.62%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Ammodendron karelinii

Citrus japonica

Duguetia chrysocarpa

Phaseolus coccineus