Chiricanine A

Details

• Internal ID: db2e1a2e-776a-434c-97ad-1c08bbcd10b8
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 2-(3-methylbut-2-enyl)-5-[(E)-2-phenylethenyl]benzene-1,3-diol
• SMILES (Canonical): CC(=CCC1=C(C=C(C=C1O)C=CC2=CC=CC=C2)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=C(C=C1O)/C=C/C2=CC=CC=C2)O)C
• InChI: InChI=1S/C19H20O2/c1-14(2)8-11-17-18(20)12-16(13-19(17)21)10-9-15-6-4-3-5-7-15/h3-10,12-13,20-21H,11H2,1-2H3/b10-9+
• InChI Key: LJFRYKIVTYCTIO-MDZDMXLPSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₀O₂
• Molecular Weight: 280.40 g/mol
• Exact Mass: 280.146329876 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.78
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• Chiricanone A
• CHEMBL471087
• SCHEMBL19717932
• 2-(3-methylbut-2-enyl)-5-[(E)-2-phenylethenyl]benzene-1,3-diol
• AKOS040762922
• 350593-30-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9967	99.67%
Caco-2	+	0.5571	55.71%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7357	73.57%
OATP2B1 inhibitior	-	0.8509	85.09%
OATP1B1 inhibitior	+	0.8945	89.45%
OATP1B3 inhibitior	+	0.9517	95.17%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9088	90.88%
BSEP inhibitior	+	0.8425	84.25%
P-glycoprotein inhibitior	-	0.5463	54.63%
P-glycoprotein substrate	-	0.9439	94.39%
CYP3A4 substrate	-	0.6948	69.48%
CYP2C9 substrate	-	0.6075	60.75%
CYP2D6 substrate	-	0.6697	66.97%
CYP3A4 inhibition	+	0.5078	50.78%
CYP2C9 inhibition	+	0.9175	91.75%
CYP2C19 inhibition	+	0.9264	92.64%
CYP2D6 inhibition	-	0.6907	69.07%
CYP1A2 inhibition	+	0.9329	93.29%
CYP2C8 inhibition	-	0.6904	69.04%
CYP inhibitory promiscuity	+	0.9616	96.16%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7650	76.50%
Carcinogenicity (trinary)	Non-required	0.7260	72.60%
Eye corrosion	-	0.9652	96.52%
Eye irritation	+	0.9425	94.25%
Skin irritation	-	0.7616	76.16%
Skin corrosion	+	0.6441	64.41%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7352	73.52%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	+	0.8713	87.13%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.7121	71.21%
Acute Oral Toxicity (c)	III	0.6648	66.48%
Estrogen receptor binding	+	0.9520	95.20%
Androgen receptor binding	+	0.8942	89.42%
Thyroid receptor binding	+	0.7405	74.05%
Glucocorticoid receptor binding	+	0.8517	85.17%
Aromatase binding	+	0.8853	88.53%
PPAR gamma	+	0.9693	96.93%
Honey bee toxicity	-	0.9494	94.94%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9959	99.59%

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	97.95%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.03%	96.00%
CHEMBL2581	P07339	Cathepsin D	93.83%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	93.30%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	92.87%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.37%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.77%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.69%	93.99%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.31%	94.62%
CHEMBL221	P23219	Cyclooxygenase-1	86.18%	90.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.13%	91.71%

Plants that contains it

• Lonchocarpus chiricanus
• Rheum palmatum

Cross-Links

• PubChem: 11087176
• NPASS: NPC19808
• LOTUS: LTS0130470
• wikiData: Q105152543