4-hydroxypanduratin A

Details

• Internal ID: 6bbc751c-228b-41f4-b539-6074c1d36421
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: [(1R,2S,6R)-3-methyl-2-(3-methylbut-2-enyl)-6-phenylcyclohex-3-en-1-yl]-(2,4,6-trihydroxyphenyl)methanone
• SMILES (Canonical): CC1=CCC(C(C1CC=C(C)C)C(=O)C2=C(C=C(C=C2O)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=C2O)O)O)C3=CC=CC=C3
• InChI: InChI=1S/C25H28O4/c1-15(2)9-11-19-16(3)10-12-20(17-7-5-4-6-8-17)23(19)25(29)24-21(27)13-18(26)14-22(24)28/h4-10,13-14,19-20,23,26-28H,11-12H2,1-3H3/t19-,20+,23-/m1/s1
• InChI Key: AYPOOQWQTQIRFW-ZRCGQRJVSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₄
• Molecular Weight: 392.50 g/mol
• Exact Mass: 392.19875937 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.71
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• (-)-Hydroxypanduratin A
• CHEMBL210882
• Hydroxypanduratin A
• BDBM50185447
• [(1R,2S,6R)-3-methyl-2-(3-methylbut-2-enyl)-6-phenylcyclohex-3-en-1-yl]-(2,4,6-trihydroxyphenyl)methanone
• (-)-(2,4,6-Trihydroxyphenyl)[3'-methyl-2'-(3''-methylbut-2''-enyl)-6'-phenylcyclohex-3'-enyl]methanone
• [(1R,2S,6R)-3-methyl-2-(3-methylbut-2-enyl)-6-phenyl-cyclohex-3-en-1-yl]-(2,4,6-trihydroxyphenyl)methanone
• [3-Methyl-2-(3-methyl-but-2-enyl)-6-phenyl-cyclohex-3-enyl]-(2,4,6-trihydroxy-phenyl)-methanone
• InChI=1/C25H28O4/c1-15(2)9-11-19-16(3)10-12-20(17-7-5-4-6-8-17)23(19)25(29)24-21(27)13-18(26)14-22(24)28/h4-10,13-14,19-20,23,26-28H,11-12H2,1-3H3/t19-,20+,23-/m1/s
• Methanone, (2,4,6-trihydroxyphenyl)[(1R,2S,6R)-3-methyl-2-(3-methyl-2-butenyl)-6-phenyl-3-cyclohexen-1-yl]-
• methanone, [(1R,2S,6R)-3-methyl-2-(3-methyl-2-butenyl)-6-phenyl-3-cyclohexen-1-yl](2,4,6-trihydroxyphenyl)-
• rel-[(1R,2S,6R)-3-methyl-2-(3-methylbut-2-en-1-yl)-6-phenylcyclohex-3-en-1-yl](2,4,6-trihydroxyphenyl)methanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9957	99.57%
Caco-2	+	0.7060	70.60%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8756	87.56%
OATP2B1 inhibitior	-	0.5870	58.70%
OATP1B1 inhibitior	+	0.9075	90.75%
OATP1B3 inhibitior	+	0.8759	87.59%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6991	69.91%
P-glycoprotein inhibitior	-	0.4627	46.27%
P-glycoprotein substrate	-	0.7600	76.00%
CYP3A4 substrate	+	0.5488	54.88%
CYP2C9 substrate	-	0.7891	78.91%
CYP2D6 substrate	-	0.8268	82.68%
CYP3A4 inhibition	+	0.5143	51.43%
CYP2C9 inhibition	+	0.9090	90.90%
CYP2C19 inhibition	+	0.9436	94.36%
CYP2D6 inhibition	-	0.7921	79.21%
CYP1A2 inhibition	+	0.8992	89.92%
CYP2C8 inhibition	+	0.7324	73.24%
CYP inhibitory promiscuity	+	0.9385	93.85%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7383	73.83%
Carcinogenicity (trinary)	Non-required	0.7406	74.06%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.8538	85.38%
Skin irritation	-	0.7874	78.74%
Skin corrosion	-	0.9292	92.92%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7920	79.20%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.5407	54.07%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.5838	58.38%
Acute Oral Toxicity (c)	III	0.7345	73.45%
Estrogen receptor binding	+	0.8033	80.33%
Androgen receptor binding	+	0.7645	76.45%
Thyroid receptor binding	+	0.6729	67.29%
Glucocorticoid receptor binding	+	0.8343	83.43%
Aromatase binding	+	0.7126	71.26%
PPAR gamma	+	0.9093	90.93%
Honey bee toxicity	-	0.8557	85.57%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
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	98.15%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.13%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	94.89%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.80%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	91.83%	94.73%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	90.69%	97.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.44%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.63%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	86.59%	90.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.36%	94.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.83%	97.09%
CHEMBL4208	P20618	Proteasome component C5	84.30%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.23%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.90%	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
• 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: 636530
• NPASS: NPC175738
• ChEMBL: CHEMBL210882
• LOTUS: LTS0051680
• wikiData: Q104921311