Panduratin C

Details

• Internal ID: fb9bdee8-2f25-4984-a5cf-4483c085d6e9
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (2,4-dihydroxy-6-methoxyphenyl)-[(1R,2S,6R)-6-(4-hydroxyphenyl)-3-methyl-2-(3-methylbut-2-enyl)cyclohex-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=C(C=C3)O
• 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=C(C=C3)O
• InChI: InChI=1S/C26H30O5/c1-15(2)5-11-20-16(3)6-12-21(17-7-9-18(27)10-8-17)24(20)26(30)25-22(29)13-19(28)14-23(25)31-4/h5-10,13-14,20-21,24,27-29H,11-12H2,1-4H3/t20-,21+,24-/m1/s1
• InChI Key: UDUSGBMXZRNBJM-ZFGGDYGUSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₅
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.20932405 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.72
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• (+/-)-panduratin C
• CHEMBL398871
• (2,4-dihydroxy-6-methoxyphenyl)-[(1R,2S,6R)-6-(4-hydroxyphenyl)-3-methyl-2-(3-methylbut-2-enyl)cyclohex-3-en-1-yl]methanone
• (2,4-dihydroxy-6-methoxy-phenyl)-[(1R,2S,6R)-6-(4-hydroxyphenyl)-3-methyl-2-(3-methylbut-2-enyl)cyclohex-3-en-1-yl]methanone
• Methanone, (2,4-dihydroxy-6-methoxyphenyl)[(1R,2S,6R)-6-(4-hydroxyphenyl)-3-methyl-2-(3-methyl-2-butenyl)-3-cyclohexen-1-yl]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.7693	76.93%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8798	87.98%
OATP2B1 inhibitior	-	0.5864	58.64%
OATP1B1 inhibitior	+	0.8956	89.56%
OATP1B3 inhibitior	+	0.8448	84.48%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8326	83.26%
P-glycoprotein inhibitior	+	0.6744	67.44%
P-glycoprotein substrate	-	0.5858	58.58%
CYP3A4 substrate	+	0.6316	63.16%
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	+	0.7617	76.17%
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	-	0.8047	80.47%
Skin irritation	-	0.8239	82.39%
Skin corrosion	-	0.9558	95.58%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4409	44.09%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.7651	76.51%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	+	0.4759	47.59%
Acute Oral Toxicity (c)	III	0.6726	67.26%
Estrogen receptor binding	+	0.7992	79.92%
Androgen receptor binding	+	0.8115	81.15%
Thyroid receptor binding	+	0.6589	65.89%
Glucocorticoid receptor binding	+	0.8726	87.26%
Aromatase binding	+	0.5897	58.97%
PPAR gamma	+	0.8760	87.60%
Honey bee toxicity	-	0.7129	71.29%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
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	98.06%	91.11%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	96.59%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	96.44%	96.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.39%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.25%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.98%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.28%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.59%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.41%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.16%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.46%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.90%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	86.77%	94.73%
CHEMBL4208	P20618	Proteasome component C5	84.82%	90.00%
CHEMBL3194	P02766	Transthyretin	83.81%	90.71%
CHEMBL2535	P11166	Glucose transporter	81.62%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.53%	89.00%

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
• 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

Cross-Links

• PubChem: 6483647
• NPASS: NPC65920
• LOTUS: LTS0142513
• wikiData: Q105270530