Bruceolline H

Details

• Internal ID: 2592ce91-9c6b-4477-bfa3-d7eb2ff09208
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Hydroxyindoles
• IUPAC Name: 6-hydroxy-3,3-dimethyl-4H-cyclopenta[b]indole-1,2-dione
• InChI: InChI=1S/C13H11NO3/c1-13(2)11-9(10(16)12(13)17)7-4-3-6(15)5-8(7)14-11/h3-5,14-15H,1-2H3
• InChI Key: JGPRUCFGUSXLES-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₁NO₃
• Molecular Weight: 229.23 g/mol
• Exact Mass: 229.07389321 g/mol
• Topological Polar Surface Area (TPSA): 70.20 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.92
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• CHEBI:68919
• CHEMBL1922989
• DTXSID301179235
• Q27137274
• 3,4-Dihydro-6-hydroxy-3,3-dimethylcyclopent[b]indole-1,2-dione
• 6-hydroxy-3,3-dimethyl-3,4-dihydrocyclopenta[b]indole-1,2-dione
• 1346764-74-6

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9923	99.23%
Caco-2	-	0.7609	76.09%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8018	80.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8316	83.16%
OATP1B3 inhibitior	+	0.9341	93.41%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9106	91.06%
P-glycoprotein inhibitior	-	0.9579	95.79%
P-glycoprotein substrate	-	0.8863	88.63%
CYP3A4 substrate	-	0.5236	52.36%
CYP2C9 substrate	-	0.8095	80.95%
CYP2D6 substrate	-	0.8428	84.28%
CYP3A4 inhibition	-	0.8400	84.00%
CYP2C9 inhibition	-	0.5521	55.21%
CYP2C19 inhibition	-	0.5296	52.96%
CYP2D6 inhibition	-	0.7694	76.94%
CYP1A2 inhibition	+	0.7036	70.36%
CYP2C8 inhibition	-	0.5847	58.47%
CYP inhibitory promiscuity	+	0.5479	54.79%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9043	90.43%
Carcinogenicity (trinary)	Non-required	0.5444	54.44%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.5782	57.82%
Skin irritation	-	0.7687	76.87%
Skin corrosion	-	0.9047	90.47%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7375	73.75%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.7034	70.34%
skin sensitisation	-	0.8122	81.22%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5449	54.49%
Acute Oral Toxicity (c)	III	0.6587	65.87%
Estrogen receptor binding	+	0.6006	60.06%
Androgen receptor binding	+	0.8198	81.98%
Thyroid receptor binding	-	0.5366	53.66%
Glucocorticoid receptor binding	-	0.6137	61.37%
Aromatase binding	+	0.6447	64.47%
PPAR gamma	+	0.5750	57.50%
Honey bee toxicity	-	0.9455	94.55%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.7899	78.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.44%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.20%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.74%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.85%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	91.61%	94.75%
CHEMBL1951	P21397	Monoamine oxidase A	91.04%	91.49%
CHEMBL242	Q92731	Estrogen receptor beta	89.91%	98.35%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.85%	89.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.62%	91.71%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	85.55%	91.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.23%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.03%	99.23%
CHEMBL4040	P28482	MAP kinase ERK2	83.75%	83.82%
CHEMBL2535	P11166	Glucose transporter	83.29%	98.75%
CHEMBL255	P29275	Adenosine A2b receptor	83.02%	98.59%
CHEMBL4208	P20618	Proteasome component C5	81.43%	90.00%

Plants that contains it

• Brucea mollis

Cross-Links

• PubChem: 56833856
• LOTUS: LTS0118725
• wikiData: Q27137274