Petasiphenone

Details

• Internal ID: ecb010e1-8412-44da-aa31-2a29679bd8c5
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: [2-(3,4-dihydroxyphenyl)-2-oxoethyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=C(C=C1C=CC(=O)OCC(=O)C2=CC(=C(C=C2)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C/C(=O)OCC(=O)C2=CC(=C(C=C2)O)O)O)O
• InChI: InChI=1S/C17H14O7/c18-12-4-1-10(7-14(12)20)2-6-17(23)24-9-16(22)11-3-5-13(19)15(21)8-11/h1-8,18-21H,9H2/b6-2+
• InChI Key: DPMVCMFEBYVTFB-QHHAFSJGSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₇
• Molecular Weight: 330.29 g/mol
• Exact Mass: 330.07395278 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.95
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• UNII-80JLG0ZRHZ
• 3,4-Dihydroxy-phenacyl caffeate
• 80JLG0ZRHZ
• 3,4-Dihydroxyphenacyl caffeate
• 162616-81-1
• 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, 2-(3,4-dihydroxyphenyl)-2-oxoethyl ester, (2E)-
• 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, 2-(3,4-dihydroxyphenyl)-2-oxoethyl ester, (E)-
• CHEBI:174449
• DTXSID801141069
• Q27269148
• [2-(3,4-dihydroxyphenyl)-2-oxoethyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 2-(3,4-Dihydroxyphenyl)-2-oxoethyl (2E)-3-(3,4-dihydroxyphenyl)-2-propenoate
• 2-(3,4-dihydroxyphenyl)-2-oxoethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9422	94.22%
Caco-2	-	0.8197	81.97%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8848	88.48%
OATP2B1 inhibitior	-	0.5793	57.93%
OATP1B1 inhibitior	+	0.9423	94.23%
OATP1B3 inhibitior	+	0.9017	90.17%
MATE1 inhibitior	-	0.5000	50.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4860	48.60%
P-glycoprotein inhibitior	-	0.8703	87.03%
P-glycoprotein substrate	-	0.9478	94.78%
CYP3A4 substrate	-	0.5969	59.69%
CYP2C9 substrate	-	0.6019	60.19%
CYP2D6 substrate	-	0.8608	86.08%
CYP3A4 inhibition	-	0.8225	82.25%
CYP2C9 inhibition	+	0.5226	52.26%
CYP2C19 inhibition	-	0.5715	57.15%
CYP2D6 inhibition	-	0.8674	86.74%
CYP1A2 inhibition	+	0.6543	65.43%
CYP2C8 inhibition	+	0.6934	69.34%
CYP inhibitory promiscuity	-	0.7339	73.39%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8116	81.16%
Carcinogenicity (trinary)	Non-required	0.6666	66.66%
Eye corrosion	-	0.9938	99.38%
Eye irritation	-	0.4775	47.75%
Skin irritation	-	0.8062	80.62%
Skin corrosion	-	0.9627	96.27%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6623	66.23%
Micronuclear	+	0.6508	65.08%
Hepatotoxicity	-	0.5822	58.22%
skin sensitisation	+	0.5123	51.23%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.6852	68.52%
Acute Oral Toxicity (c)	III	0.7928	79.28%
Estrogen receptor binding	+	0.8872	88.72%
Androgen receptor binding	+	0.8337	83.37%
Thyroid receptor binding	-	0.5393	53.93%
Glucocorticoid receptor binding	+	0.6360	63.60%
Aromatase binding	+	0.6644	66.44%
PPAR gamma	+	0.6628	66.28%
Honey bee toxicity	-	0.9002	90.02%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9938	99.38%

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	98.29%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.09%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	97.82%	91.49%
CHEMBL3194	P02766	Transthyretin	96.23%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.52%	96.00%
CHEMBL4208	P20618	Proteasome component C5	91.18%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.36%	99.17%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	89.82%	80.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.62%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.48%	89.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.98%	91.71%

Plants that contains it

• Acacia paradoxa
• Actaea racemosa
• Adonis sutchuenensis
• Astragalus ernestii
• Berneuxia thibetica
• Bongardia chrysogonum
• Eragrostis curvula
• Fritillaria meleagris
• Isophysis tasmanica
• Matricaria discoidea
• Metasequoia glyptostroboides
• Petasites japonicus
• Philenoptera laxiflora
• Plantago lundborgii
• Sideritis arborescens
• Solanum pseudoquina
• Triadica sebifera

Cross-Links

• PubChem: 16066851
• NPASS: NPC176365
• LOTUS: LTS0263997
• wikiData: Q27269148