Azaphilone

Details

• Internal ID: afddfe9b-2cb7-4b04-a26f-7af7974f572b
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > p-Hydroxybenzoic acid esters > p-Hydroxybenzoic acid alkyl esters
• IUPAC Name: [(7R,8R,8aR)-7-hydroxy-7-methyl-6-oxo-3-[(E)-prop-1-enyl]-8,8a-dihydro-1H-isochromen-8-yl] 2,4-dihydroxy-6-methylbenzoate
• SMILES (Canonical): CC=CC1=CC2=CC(=O)C(C(C2CO1)OC(=O)C3=C(C=C(C=C3C)O)O)(C)O
• SMILES (Isomeric): C/C=C/C1=CC2=CC(=O)[C@]([C@@H]([C@H]2CO1)OC(=O)C3=C(C=C(C=C3C)O)O)(C)O
• InChI: InChI=1S/C21H22O7/c1-4-5-14-7-12-8-17(24)21(3,26)19(15(12)10-27-14)28-20(25)18-11(2)6-13(22)9-16(18)23/h4-9,15,19,22-23,26H,10H2,1-3H3/b5-4+/t15-,19+,21-/m0/s1
• InChI Key: HNVJWWBKFFDQAA-NRKPLWJESA-N
• Popularity: 143 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₇
• Molecular Weight: 386.40 g/mol
• Exact Mass: 386.13655304 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.30
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• Berkazaphilone C
• CHEMBL2024575

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9025	90.25%
Caco-2	-	0.6029	60.29%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6999	69.99%
OATP2B1 inhibitior	-	0.7215	72.15%
OATP1B1 inhibitior	+	0.8763	87.63%
OATP1B3 inhibitior	+	0.9255	92.55%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5869	58.69%
P-glycoprotein inhibitior	-	0.6225	62.25%
P-glycoprotein substrate	-	0.6148	61.48%
CYP3A4 substrate	+	0.6518	65.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8982	89.82%
CYP3A4 inhibition	-	0.8559	85.59%
CYP2C9 inhibition	+	0.6278	62.78%
CYP2C19 inhibition	-	0.5438	54.38%
CYP2D6 inhibition	-	0.8379	83.79%
CYP1A2 inhibition	+	0.7092	70.92%
CYP2C8 inhibition	+	0.6459	64.59%
CYP inhibitory promiscuity	+	0.6337	63.37%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5449	54.49%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9243	92.43%
Skin irritation	-	0.6590	65.90%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3965	39.65%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	-	0.7651	76.51%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6809	68.09%
Acute Oral Toxicity (c)	III	0.4459	44.59%
Estrogen receptor binding	+	0.8767	87.67%
Androgen receptor binding	+	0.7191	71.91%
Thyroid receptor binding	+	0.6325	63.25%
Glucocorticoid receptor binding	+	0.7745	77.45%
Aromatase binding	+	0.6197	61.97%
PPAR gamma	+	0.6383	63.83%
Honey bee toxicity	-	0.7235	72.35%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9808	98.08%

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	99.32%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.28%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.85%	89.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	93.51%	96.12%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.86%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	92.00%	91.19%
CHEMBL2581	P07339	Cathepsin D	90.12%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.04%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.15%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.02%	99.23%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.84%	93.40%
CHEMBL4208	P20618	Proteasome component C5	86.53%	90.00%
CHEMBL3194	P02766	Transthyretin	85.83%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.79%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.38%	92.94%
CHEMBL3401	O75469	Pregnane X receptor	82.50%	94.73%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.43%	94.42%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.23%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.74%	97.14%
CHEMBL1937	Q92769	Histone deacetylase 2	80.12%	94.75%

Plants that contains it

• Clibadium microcephalum
• Globularia nudicaulis
• Helianthus pumilus
• Leucas aspera
• Stemona parviflora

Cross-Links

• PubChem: 57384025
• NPASS: NPC76041
• ChEMBL: CHEMBL2024575