Xenognosin A

Details

• Internal ID: 50274815-3c27-42bc-ad69-14dd61de40a9
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Cinnamylphenols
• IUPAC Name: 4-[(E)-3-(4-hydroxyphenyl)prop-2-enyl]-3-methoxyphenol
• SMILES (Canonical): COC1=C(C=CC(=C1)O)CC=CC2=CC=C(C=C2)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)O)C/C=C/C2=CC=C(C=C2)O
• InChI: InChI=1S/C16H16O3/c1-19-16-11-15(18)10-7-13(16)4-2-3-12-5-8-14(17)9-6-12/h2-3,5-11,17-18H,4H2,1H3/b3-2+
• InChI Key: LOHIEGDVOARVPJ-NSCUHMNNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₆O₃
• Molecular Weight: 256.30 g/mol
• Exact Mass: 256.109944368 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.36
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• xenognosin
• 76907-79-4
• UNII-02F52L203E
• Phenol, 4-((2E)-3-(4-hydroxyphenyl)-2-propen-1-yl)-3-methoxy-
• 02F52L203E
• CHEBI:10075
• Phenol, 4-((2E)-3-(4-hydroxyphenyl)-2-propenyl)-3-methoxy-
• C08731
• 1-(4-hydroxyphenyl)-3-(4-hydroxy-2-methoxyphenyl)propene
• CHEMBL1087026
• 4-[(E)-3-(4-hydroxyphenyl)prop-2-enyl]-3-methoxyphenol
• DTXSID801318553
• 4-[3-(4-hydroxyphenyl)prop-2-enyl]-3-methoxy-phenol
• Q27108572
• 4-[3-(4-Hydroxyphenyl)-2-propenyl]-3-methoxyphenol, 9CI
• 4-[(2E)-3-(4-hydroxyphenyl)prop-2-en-1-yl]-3-methoxyphenol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9940	99.40%
Caco-2	+	0.8899	88.99%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8505	85.05%
OATP2B1 inhibitior	-	0.8511	85.11%
OATP1B1 inhibitior	+	0.6841	68.41%
OATP1B3 inhibitior	+	0.9609	96.09%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5966	59.66%
P-glycoprotein inhibitior	-	0.8613	86.13%
P-glycoprotein substrate	-	0.8110	81.10%
CYP3A4 substrate	-	0.5932	59.32%
CYP2C9 substrate	+	0.5888	58.88%
CYP2D6 substrate	+	0.4021	40.21%
CYP3A4 inhibition	-	0.8281	82.81%
CYP2C9 inhibition	+	0.6629	66.29%
CYP2C19 inhibition	+	0.9217	92.17%
CYP2D6 inhibition	-	0.8506	85.06%
CYP1A2 inhibition	+	0.8758	87.58%
CYP2C8 inhibition	+	0.7466	74.66%
CYP inhibitory promiscuity	+	0.9309	93.09%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.6356	63.56%
Carcinogenicity (trinary)	Non-required	0.5391	53.91%
Eye corrosion	-	0.9608	96.08%
Eye irritation	+	0.9321	93.21%
Skin irritation	-	0.6612	66.12%
Skin corrosion	-	0.8312	83.12%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6709	67.09%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.6697	66.97%
skin sensitisation	+	0.4882	48.82%
Respiratory toxicity	-	0.8333	83.33%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.8250	82.50%
Nephrotoxicity	-	0.5952	59.52%
Acute Oral Toxicity (c)	III	0.6245	62.45%
Estrogen receptor binding	+	0.8923	89.23%
Androgen receptor binding	+	0.6633	66.33%
Thyroid receptor binding	+	0.5546	55.46%
Glucocorticoid receptor binding	+	0.7542	75.42%
Aromatase binding	+	0.8311	83.11%
PPAR gamma	+	0.8036	80.36%
Honey bee toxicity	-	0.8581	85.81%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9772	97.72%

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	97.03%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.92%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.59%	96.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	92.62%	89.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.87%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.22%	99.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	90.56%	91.71%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.97%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.65%	95.56%
CHEMBL242	Q92731	Estrogen receptor beta	88.23%	98.35%
CHEMBL3194	P02766	Transthyretin	87.68%	90.71%
CHEMBL4208	P20618	Proteasome component C5	86.14%	90.00%
CHEMBL2535	P11166	Glucose transporter	85.91%	98.75%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	82.94%	96.09%
CHEMBL2581	P07339	Cathepsin D	82.92%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.17%	95.89%

Plants that contains it

• Boenninghausenia albiflora
• Citrus aurantiifolia
• Citrus deliciosa
• Citrus limon
• Dalbergia parviflora
• Lathyrus oleraceus
• Luvunga scandens
• Ruta graveolens
• Zanthoxylum ailanthoides
• Zanthoxylum americanum

Cross-Links

• PubChem: 5281296
• NPASS: NPC185541
• LOTUS: LTS0100361
• wikiData: Q27108572