Isopanduratin A

Details

• Internal ID: 434b98ed-6ed5-44bc-ac4a-751ddc0c4767
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (2,4-dihydroxy-6-methoxyphenyl)-[(1R,2S,6R)-3-methyl-2-(3-methylbut-2-enyl)-6-phenylcyclohex-3-en-1-yl]methanone
• SMILES (Canonical): CC1=CCC(C(C1CC=C(C)C)C(=O)C2=C(C=C(C=C2OC)O)O)C3=CC=CC=C3
• SMILES (Isomeric): CC1=CC[C@H]([C@@H]([C@@H]1CC=C(C)C)C(=O)C2=C(C=C(C=C2OC)O)O)C3=CC=CC=C3
• InChI: InChI=1S/C26H30O4/c1-16(2)10-12-20-17(3)11-13-21(18-8-6-5-7-9-18)24(20)26(29)25-22(28)14-19(27)15-23(25)30-4/h5-11,14-15,20-21,24,27-28H,12-13H2,1-4H3/t20-,21+,24-/m1/s1
• InChI Key: DIHCGASLQARQMP-ZFGGDYGUSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₄
• Molecular Weight: 406.50 g/mol
• Exact Mass: 406.21440943 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 6.01
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• (-)-isopanduratin A2
• CHEMBL398503
• (2,4-Dihydroxy-6-methoxyphenyl)-[(1R,2S,6R)-3-methyl-2-(3-methylbut-2-enyl)-6-phenylcyclohex-3-en-1-yl]methanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.7373	73.73%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8798	87.98%
OATP2B1 inhibitior	-	0.8633	86.33%
OATP1B1 inhibitior	+	0.9131	91.31%
OATP1B3 inhibitior	+	0.8448	84.48%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8227	82.27%
P-glycoprotein inhibitior	+	0.7468	74.68%
P-glycoprotein substrate	-	0.6540	65.40%
CYP3A4 substrate	+	0.6117	61.17%
CYP2C9 substrate	-	0.7904	79.04%
CYP2D6 substrate	-	0.8029	80.29%
CYP3A4 inhibition	-	0.6279	62.79%
CYP2C9 inhibition	+	0.8401	84.01%
CYP2C19 inhibition	+	0.9529	95.29%
CYP2D6 inhibition	-	0.7652	76.52%
CYP1A2 inhibition	+	0.8348	83.48%
CYP2C8 inhibition	+	0.8372	83.72%
CYP inhibitory promiscuity	+	0.9354	93.54%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7627	76.27%
Carcinogenicity (trinary)	Non-required	0.7440	74.40%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8831	88.31%
Skin irritation	-	0.8239	82.39%
Skin corrosion	-	0.9558	95.58%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7603	76.03%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.7651	76.51%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	+	0.4777	47.77%
Acute Oral Toxicity (c)	III	0.6726	67.26%
Estrogen receptor binding	+	0.8155	81.55%
Androgen receptor binding	+	0.7507	75.07%
Thyroid receptor binding	+	0.5992	59.92%
Glucocorticoid receptor binding	+	0.8546	85.46%
Aromatase binding	+	0.6529	65.29%
PPAR gamma	+	0.8938	89.38%
Honey bee toxicity	-	0.7354	73.54%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	98.45%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.01%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	95.60%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.11%	95.56%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	93.53%	97.21%
CHEMBL2581	P07339	Cathepsin D	93.24%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.89%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.34%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	87.00%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.92%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.19%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.52%	95.89%
CHEMBL2535	P11166	Glucose transporter	82.39%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.41%	89.62%
CHEMBL4208	P20618	Proteasome component C5	80.31%	90.00%

Plants that contains it

• Amorphophallus konjac
• Aniba santalodora
• Astragalus circassicus
• Beilschmiedia madang
• Bethencourtia palmensis
• Boesenbergia rotunda
• Boswellia ovalifoliolata
• Campanula bayerniana
• Caucasalia pontica
• Centaurea scoparia
• Centaurea sphaerocephala subsp. sphaerocephala
• Colchicum filifolium
• Dacrycarpus dacrydioides
• Dialium excelsum
• Drymaria cordata
• Erythrina subumbrans
• Euphorbia hylonoma
• Gaillardia coahuilensis
• Hardenbergia violacea
• Heliotropium marifolium
• Helleborus niger subsp. macranthus
• Lepechinia urbanii
• Lindelofia anchusoides subsp. macrostyla
• Lonchocarpus chiricanus
• Maclura cochinchinensis
• Mentzelia decapetala
• Mimosa pigra
• Mucuna holtonii
• Oncosiphon sabulosus
• Pterocaulon serrulatum
• Pulsatilla chinensis
• Quercus marilandica
• Rubia argyi
• Salix rosmarinifolia
• Salvia lavanduloides
• Salvia patens
• Salvia virgata
• Xylopia emarginata

Cross-Links

• PubChem: 10069916
• NPASS: NPC253422
• LOTUS: LTS0047188
• wikiData: Q104981346