Chiricanine D

Details

• Internal ID: e0ecdeb1-5c89-413f-8cd5-bbbed5d5d114
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 2,2-dimethyl-6-(3-methylbut-2-enyl)-5-[(E)-2-phenylethenyl]-3,4-dihydrochromene-3,7-diol
• SMILES (Canonical): CC(=CCC1=C(C2=C(C=C1O)OC(C(C2)O)(C)C)C=CC3=CC=CC=C3)C
• SMILES (Isomeric): CC(=CCC1=C(C2=C(C=C1O)OC(C(C2)O)(C)C)/C=C/C3=CC=CC=C3)C
• InChI: InChI=1S/C24H28O3/c1-16(2)10-12-19-18(13-11-17-8-6-5-7-9-17)20-14-23(26)24(3,4)27-22(20)15-21(19)25/h5-11,13,15,23,25-26H,12,14H2,1-4H3/b13-11+
• InChI Key: KKSDBZMBXBGTRS-ACCUITESSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₃
• Molecular Weight: 364.50 g/mol
• Exact Mass: 364.20384475 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 5.15
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• CHEMBL511800

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9959	99.59%
Caco-2	+	0.7667	76.67%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6612	66.12%
OATP2B1 inhibitior	-	0.8551	85.51%
OATP1B1 inhibitior	+	0.8480	84.80%
OATP1B3 inhibitior	+	0.9655	96.55%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9790	97.90%
P-glycoprotein inhibitior	+	0.7083	70.83%
P-glycoprotein substrate	-	0.7228	72.28%
CYP3A4 substrate	+	0.5360	53.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4111	41.11%
CYP3A4 inhibition	-	0.9389	93.89%
CYP2C9 inhibition	-	0.5397	53.97%
CYP2C19 inhibition	+	0.7357	73.57%
CYP2D6 inhibition	-	0.8135	81.35%
CYP1A2 inhibition	-	0.5775	57.75%
CYP2C8 inhibition	+	0.7746	77.46%
CYP inhibitory promiscuity	+	0.5846	58.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6638	66.38%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.8120	81.20%
Skin irritation	-	0.7467	74.67%
Skin corrosion	-	0.9171	91.71%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8289	82.89%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.6135	61.35%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6386	63.86%
Acute Oral Toxicity (c)	III	0.5812	58.12%
Estrogen receptor binding	+	0.8842	88.42%
Androgen receptor binding	+	0.8074	80.74%
Thyroid receptor binding	+	0.7559	75.59%
Glucocorticoid receptor binding	+	0.7818	78.18%
Aromatase binding	+	0.6695	66.95%
PPAR gamma	+	0.8950	89.50%
Honey bee toxicity	-	0.8704	87.04%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9783	97.83%

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	99.67%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.59%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.94%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	94.09%	90.17%
CHEMBL2581	P07339	Cathepsin D	93.83%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.27%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.03%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	90.00%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	89.02%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.59%	96.09%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	82.85%	89.44%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.24%	89.00%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	82.12%	92.68%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.56%	94.62%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	80.99%	85.49%

Plants that contains it

• Lonchocarpus chiricanus

Cross-Links

• PubChem: 10981364
• LOTUS: LTS0110325
• wikiData: Q105142339