Berkazaphilone A

Details

• Internal ID: 4937103a-ad78-4c92-8c21-2bbabe403775
• Taxonomy: Organoheterocyclic compounds > Azaphilones
• IUPAC Name: (7S,8R,8aR)-8-hydroxy-7-methyl-3-[(E)-prop-1-enyl]-1,7,8,8a-tetrahydroisochromen-6-one
• SMILES (Canonical): CC=CC1=CC2=CC(=O)C(C(C2CO1)O)C
• SMILES (Isomeric): C/C=C/C1=CC2=CC(=O)[C@H]([C@@H]([C@H]2CO1)O)C
• InChI: InChI=1S/C13H16O3/c1-3-4-10-5-9-6-12(14)8(2)13(15)11(9)7-16-10/h3-6,8,11,13,15H,7H2,1-2H3/b4-3+/t8-,11+,13+/m1/s1
• InChI Key: CHORXUQBNMRTBR-HKBNWMJQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆O₃
• Molecular Weight: 220.26 g/mol
• Exact Mass: 220.109944368 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.60
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• CHEBI:189263
• (7S,8R,8aR)-8-hydroxy-7-methyl-3-[(E)-prop-1-enyl]-1,7,8,8a-tetrahydroisochromen-6-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9962	99.62%
Caco-2	+	0.6825	68.25%
Blood Brain Barrier	-	0.5072	50.72%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7679	76.79%
OATP2B1 inhibitior	-	0.8618	86.18%
OATP1B1 inhibitior	+	0.8960	89.60%
OATP1B3 inhibitior	+	0.9775	97.75%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8422	84.22%
P-glycoprotein inhibitior	-	0.9683	96.83%
P-glycoprotein substrate	-	0.8289	82.89%
CYP3A4 substrate	-	0.5119	51.19%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8791	87.91%
CYP3A4 inhibition	-	0.7509	75.09%
CYP2C9 inhibition	-	0.7721	77.21%
CYP2C19 inhibition	-	0.5792	57.92%
CYP2D6 inhibition	-	0.8993	89.93%
CYP1A2 inhibition	+	0.7056	70.56%
CYP2C8 inhibition	-	0.9294	92.94%
CYP inhibitory promiscuity	-	0.6077	60.77%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.6093	60.93%
Eye corrosion	-	0.9583	95.83%
Eye irritation	-	0.8551	85.51%
Skin irritation	-	0.5692	56.92%
Skin corrosion	-	0.9483	94.83%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6689	66.89%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.5975	59.75%
skin sensitisation	-	0.6701	67.01%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6079	60.79%
Acute Oral Toxicity (c)	III	0.3919	39.19%
Estrogen receptor binding	-	0.5907	59.07%
Androgen receptor binding	-	0.5465	54.65%
Thyroid receptor binding	-	0.7591	75.91%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.7881	78.81%
PPAR gamma	-	0.6595	65.95%
Honey bee toxicity	-	0.8001	80.01%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.7876	78.76%

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	95.40%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.32%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.15%	100.00%
CHEMBL2581	P07339	Cathepsin D	90.47%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.35%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.55%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.90%	96.77%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.38%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.84%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.78%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	81.35%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.93%	96.09%

Plants that contains it

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

Cross-Links

• PubChem: 57379196
• NPASS: NPC152539
• LOTUS: LTS0012779
• wikiData: Q75059512