Avicennol

Details

• Internal ID: 8a77355f-313f-4ad0-aefa-d6c308398f4c
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: 6-[(E)-3-hydroxy-3-methylbut-1-enyl]-5-methoxy-2,2-dimethylpyrano[2,3-h]chromen-8-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C3=C(C(=C2OC)C=CC(C)(C)O)OC(=O)C=C3)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C3=C(C(=C2OC)/C=C/C(C)(C)O)OC(=O)C=C3)C
• InChI: InChI=1S/C20H22O5/c1-19(2,22)10-8-13-16(23-5)14-9-11-20(3,4)25-18(14)12-6-7-15(21)24-17(12)13/h6-11,22H,1-5H3/b10-8+
• InChI Key: AXYRILDCSATJFU-CSKARUKUSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₅
• Molecular Weight: 342.40 g/mol
• Exact Mass: 342.14672380 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.77
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• Trans-Avicennol
• 6-[(E)-3-hydroxy-3-methyl-but-1-enyl]-5-methoxy-2,2-dimethyl-pyrano[2,3-h]chromen-8-one
• CHEMBL258230
• BDBM50379307
• 6-[(E)-3-hydroxy-3-methylbut-1-enyl]-5-methoxy-2,2-dimethylpyrano[2,3-h]chromen-8-one
• 56110-68-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9811	98.11%
Caco-2	+	0.5250	52.50%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7496	74.96%
OATP2B1 inhibitior	-	0.7233	72.33%
OATP1B1 inhibitior	+	0.8749	87.49%
OATP1B3 inhibitior	+	0.9674	96.74%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7914	79.14%
P-glycoprotein inhibitior	-	0.4734	47.34%
P-glycoprotein substrate	-	0.6973	69.73%
CYP3A4 substrate	+	0.6050	60.50%
CYP2C9 substrate	-	0.6589	65.89%
CYP2D6 substrate	-	0.8388	83.88%
CYP3A4 inhibition	-	0.5138	51.38%
CYP2C9 inhibition	-	0.8242	82.42%
CYP2C19 inhibition	-	0.5641	56.41%
CYP2D6 inhibition	-	0.8315	83.15%
CYP1A2 inhibition	-	0.6576	65.76%
CYP2C8 inhibition	+	0.4562	45.62%
CYP inhibitory promiscuity	-	0.6175	61.75%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9413	94.13%
Carcinogenicity (trinary)	Danger	0.6088	60.88%
Eye corrosion	-	0.9854	98.54%
Eye irritation	+	0.6711	67.11%
Skin irritation	-	0.7538	75.38%
Skin corrosion	-	0.9744	97.44%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3856	38.56%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.7449	74.49%
skin sensitisation	-	0.8661	86.61%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.6700	67.00%
Acute Oral Toxicity (c)	II	0.4457	44.57%
Estrogen receptor binding	+	0.9251	92.51%
Androgen receptor binding	+	0.5389	53.89%
Thyroid receptor binding	+	0.6590	65.90%
Glucocorticoid receptor binding	+	0.7297	72.97%
Aromatase binding	+	0.8150	81.50%
PPAR gamma	+	0.8472	84.72%
Honey bee toxicity	-	0.7653	76.53%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9798	97.98%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL261	P00915	Carbonic anhydrase I	8460 nM	Ki	PMID: 22892213
CHEMBL3594	Q16790	Carbonic anhydrase IX	780 nM; 780 nM	Ki; Ki	PMID: 22892213; via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	8980 nM	Ki	PMID: 22892213
CHEMBL3242	O43570	Carbonic anhydrase XII	770 nM; 770 nM	Ki; Ki	PMID: 22892213; via Super-PRED
CHEMBL3912	Q8N1Q1	Carbonic anhydrase XIII	29300 nM	Ki	PMID: 22892213

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.23%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.35%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.90%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.55%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.40%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	88.41%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.82%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.96%	94.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.70%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.69%	96.00%

Plants that contains it

• Asterolasia drummondii
• Philotheca apiculata
• Philotheca coccinea
• Philotheca thryptomenoides
• Zanthoxylum avicennae
• Zanthoxylum caribaeum subsp. rugosum

Cross-Links

• PubChem: 15118768
• NPASS: NPC232692
• ChEMBL: CHEMBL258230
• LOTUS: LTS0024472
• wikiData: Q104399577