Berkazaphilone B

Details

• Internal ID: 54107f7d-fec4-41f2-91e7-781f635fbe28
• Taxonomy: Organoheterocyclic compounds > Azaphilones
• IUPAC Name: [(7R,8R,8aR)-8-hydroxy-7-methyl-6-oxo-3-[(E)-prop-1-enyl]-8,8a-dihydro-1H-isochromen-7-yl] 2,4-dihydroxy-6-methylbenzoate
• SMILES (Canonical): CC=CC1=CC2=CC(=O)C(C(C2CO1)O)(C)OC(=O)C3=C(C=C(C=C3C)O)O
• SMILES (Isomeric): C/C=C/C1=CC2=CC(=O)[C@]([C@@H]([C@H]2CO1)O)(C)OC(=O)C3=C(C=C(C=C3C)O)O
• InChI: InChI=1S/C21H22O7/c1-4-5-14-7-12-8-17(24)21(3,19(25)15(12)10-27-14)28-20(26)18-11(2)6-13(22)9-16(18)23/h4-9,15,19,22-23,25H,10H2,1-3H3/b5-4+/t15-,19+,21-/m0/s1
• InChI Key: JCQWLKQBYHSHOG-NRKPLWJESA-N
• Popularity: 1 reference 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

• CHEMBL2024574

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9557	95.57%
Caco-2	-	0.6565	65.65%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6685	66.85%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8565	85.65%
OATP1B3 inhibitior	+	0.8740	87.40%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.5920	59.20%
P-glycoprotein inhibitior	-	0.5950	59.50%
P-glycoprotein substrate	-	0.6210	62.10%
CYP3A4 substrate	+	0.6761	67.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8907	89.07%
CYP3A4 inhibition	-	0.8996	89.96%
CYP2C9 inhibition	+	0.5378	53.78%
CYP2C19 inhibition	-	0.6036	60.36%
CYP2D6 inhibition	-	0.9062	90.62%
CYP1A2 inhibition	+	0.6684	66.84%
CYP2C8 inhibition	+	0.6262	62.62%
CYP inhibitory promiscuity	-	0.5203	52.03%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9918	99.18%
Carcinogenicity (trinary)	Non-required	0.5939	59.39%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9175	91.75%
Skin irritation	-	0.6874	68.74%
Skin corrosion	-	0.9406	94.06%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3980	39.80%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	+	0.5909	59.09%
skin sensitisation	-	0.7400	74.00%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7029	70.29%
Acute Oral Toxicity (c)	III	0.5391	53.91%
Estrogen receptor binding	+	0.8440	84.40%
Androgen receptor binding	+	0.7467	74.67%
Thyroid receptor binding	+	0.5275	52.75%
Glucocorticoid receptor binding	+	0.8119	81.19%
Aromatase binding	+	0.6118	61.18%
PPAR gamma	+	0.6792	67.92%
Honey bee toxicity	-	0.7193	71.93%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9814	98.14%

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	98.80%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.57%	94.45%
CHEMBL1929	P47989	Xanthine dehydrogenase	95.45%	96.12%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.73%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.20%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.79%	100.00%
CHEMBL2581	P07339	Cathepsin D	89.72%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.44%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.95%	96.09%
CHEMBL4208	P20618	Proteasome component C5	88.33%	90.00%
CHEMBL3194	P02766	Transthyretin	86.02%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.94%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	84.94%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	83.92%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.85%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.85%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.76%	99.17%
CHEMBL1937	Q92769	Histone deacetylase 2	80.34%	94.75%

Plants that contains it

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

Cross-Links

• PubChem: 57379197
• NPASS: NPC208173
• ChEMBL: CHEMBL2024574
• LOTUS: LTS0048233
• wikiData: Q77377106