Rocaglamide J

Details

• Internal ID: e4838b25-cc0a-423c-b6ff-eb9203c9fd4b
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Flavaglines
• IUPAC Name: methyl 1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate
• SMILES (Canonical): COC1=CC=C(C=C1)C23C(C(C(C2(C4=C(O3)C=C(C=C4OC)OC)O)O)C(=O)OC)C5=CC=CC=C5
• SMILES (Isomeric): COC1=CC=C(C=C1)C23C(C(C(C2(C4=C(O3)C=C(C=C4OC)OC)O)O)C(=O)OC)C5=CC=CC=C5
• InChI: InChI=1S/C28H28O8/c1-32-18-12-10-17(11-13-18)28-23(16-8-6-5-7-9-16)22(26(30)35-4)25(29)27(28,31)24-20(34-3)14-19(33-2)15-21(24)36-28/h5-15,22-23,25,29,31H,1-4H3
• InChI Key: VFTGDXPPYSWBSO-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₈O₈
• Molecular Weight: 492.50 g/mol
• Exact Mass: 492.17841785 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.14
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 147059-47-0
• SCHEMBL18835920

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9718	97.18%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7600	76.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8871	88.71%
OATP1B3 inhibitior	+	0.8323	83.23%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9597	95.97%
P-glycoprotein inhibitior	+	0.8563	85.63%
P-glycoprotein substrate	-	0.7015	70.15%
CYP3A4 substrate	+	0.6518	65.18%
CYP2C9 substrate	-	0.6173	61.73%
CYP2D6 substrate	-	0.7721	77.21%
CYP3A4 inhibition	-	0.5706	57.06%
CYP2C9 inhibition	-	0.8476	84.76%
CYP2C19 inhibition	-	0.7603	76.03%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	+	0.7704	77.04%
CYP inhibitory promiscuity	-	0.5464	54.64%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.3516	35.16%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.7804	78.04%
Skin irritation	-	0.7787	77.87%
Skin corrosion	-	0.9564	95.64%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4535	45.35%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.9233	92.33%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.7140	71.40%
Acute Oral Toxicity (c)	III	0.4467	44.67%
Estrogen receptor binding	+	0.7904	79.04%
Androgen receptor binding	+	0.8125	81.25%
Thyroid receptor binding	+	0.6555	65.55%
Glucocorticoid receptor binding	+	0.7460	74.60%
Aromatase binding	-	0.5746	57.46%
PPAR gamma	+	0.6775	67.75%
Honey bee toxicity	-	0.8385	83.85%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5851	58.51%
Fish aquatic toxicity	+	0.9811	98.11%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2052028	P60842	Eukaryotic initiation factor 4A-I	10 nM	EC50	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	794.3 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.95%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.44%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.00%	95.56%
CHEMBL240	Q12809	HERG	90.81%	89.76%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.31%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.29%	97.14%
CHEMBL4208	P20618	Proteasome component C5	88.54%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	87.69%	91.19%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.53%	96.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.40%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.36%	92.62%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	86.27%	89.44%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.09%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	85.74%	90.17%
CHEMBL2581	P07339	Cathepsin D	84.93%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.96%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.30%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.26%	99.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.14%	94.08%
CHEMBL2535	P11166	Glucose transporter	82.11%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.17%	94.00%

Plants that contains it

• Aglaia cucullata
• Aglaia elaeagnoidea
• Aglaia elliptica
• Aglaia mariannensis
• Aglaia odorata
• Aglaia rimosa
• Aglaia rubiginosa
• Aglaia spectabilis

Cross-Links

• PubChem: 4132
• LOTUS: LTS0019418
• wikiData: Q105285590