Brocaenol A

Details

• Internal ID: 7f04b67b-2851-4cfc-b879-b364056fb156
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans
• IUPAC Name: methyl (5R,5aS)-5,10,11-trihydroxy-4-methyl-1-oxo-5H-oxepino[4,3-b]chromene-5a-carboxylate
• SMILES (Canonical): CC1=COC(=O)C2=C(C3=C(C=CC=C3OC2(C1O)C(=O)OC)O)O
• SMILES (Isomeric): CC1=COC(=O)C2=C(C3=C(C=CC=C3O[C@@]2([C@@H]1O)C(=O)OC)O)O
• InChI: InChI=1S/C16H14O8/c1-7-6-23-14(20)11-12(18)10-8(17)4-3-5-9(10)24-16(11,13(7)19)15(21)22-2/h3-6,13,17-19H,1-2H3/t13-,16+/m1/s1
• InChI Key: GFYIIWHEPPLOOW-CJNGLKHVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₈
• Molecular Weight: 334.28 g/mol
• Exact Mass: 334.06886740 g/mol
• Topological Polar Surface Area (TPSA): 123.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.79
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9482	94.82%
Caco-2	-	0.5752	57.52%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5979	59.79%
OATP2B1 inhibitior	-	0.7161	71.61%
OATP1B1 inhibitior	+	0.8985	89.85%
OATP1B3 inhibitior	+	0.9284	92.84%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5434	54.34%
P-glycoprotein inhibitior	-	0.7621	76.21%
P-glycoprotein substrate	-	0.6871	68.71%
CYP3A4 substrate	+	0.6473	64.73%
CYP2C9 substrate	-	0.6131	61.31%
CYP2D6 substrate	-	0.8658	86.58%
CYP3A4 inhibition	-	0.6484	64.84%
CYP2C9 inhibition	-	0.7063	70.63%
CYP2C19 inhibition	-	0.5851	58.51%
CYP2D6 inhibition	-	0.8499	84.99%
CYP1A2 inhibition	-	0.8588	85.88%
CYP2C8 inhibition	+	0.5222	52.22%
CYP inhibitory promiscuity	-	0.5268	52.68%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9718	97.18%
Carcinogenicity (trinary)	Danger	0.5263	52.63%
Eye corrosion	-	0.9820	98.20%
Eye irritation	-	0.7198	71.98%
Skin irritation	-	0.6357	63.57%
Skin corrosion	-	0.9214	92.14%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8136	81.36%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.7694	76.94%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.7480	74.80%
Acute Oral Toxicity (c)	III	0.4323	43.23%
Estrogen receptor binding	+	0.7409	74.09%
Androgen receptor binding	+	0.6766	67.66%
Thyroid receptor binding	+	0.5396	53.96%
Glucocorticoid receptor binding	+	0.8141	81.41%
Aromatase binding	+	0.5229	52.29%
PPAR gamma	+	0.6695	66.95%
Honey bee toxicity	-	0.8783	87.83%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9582	95.82%

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	96.87%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	95.57%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.75%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.94%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.91%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.31%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.09%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	88.32%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.13%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.99%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.78%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.28%	95.50%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.61%	93.03%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.09%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	80.02%	91.19%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 54699129
• LOTUS: LTS0217138
• wikiData: Q75055202