Bruceolline N

Details

• Internal ID: b61faef5-1196-4a4b-860a-6bcb1e232543
• Taxonomy: Nucleosides, nucleotides, and analogues > Nucleoside and nucleotide analogues > 1-pyranosylindoles
• IUPAC Name: (3R)-3-[(2S)-2,3-dihydroxy-3-methylbutyl]-3-hydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]indol-2-one
• InChI: InChI=1S/C19H27NO9/c1-18(2,27)12(22)7-19(28)9-5-3-4-6-10(9)20(17(19)26)16-15(25)14(24)13(23)11(8-21)29-16/h3-6,11-16,21-25,27-28H,7-8H2,1-2H3/t11-,12+,13-,14+,15-,16-,19-/m1/s1
• InChI Key: QKHYSKWZRQYVRE-JYHHGOMKSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₇NO₉
• Molecular Weight: 413.40 g/mol
• Exact Mass: 413.16858144 g/mol
• Topological Polar Surface Area (TPSA): 171.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.46
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

• CHEBI:68925
• CHEMBL1922995
• DTXSID401111614
• Q27137280
• (3R)-3-[(2S)-2,3-dihydroxy-3-methylbutyl]-1-(beta-D-glucopyranosyl)-3-hydroxy-1,3-dihydro-2H-indol-2-one
• 1346764-94-0
• 2H-Indol-2-one, 3-[(2S)-2,3-dihydroxy-3-methylbutyl]-1-beta-D-glucopyranosyl-1,3-dihydro-3-hydroxy-, (3R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6655	66.55%
Caco-2	-	0.7645	76.45%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.4296	42.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8860	88.60%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9566	95.66%
BSEP inhibitior	-	0.8590	85.90%
P-glycoprotein inhibitior	-	0.8130	81.30%
P-glycoprotein substrate	-	0.8205	82.05%
CYP3A4 substrate	+	0.5928	59.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8206	82.06%
CYP3A4 inhibition	-	0.9062	90.62%
CYP2C9 inhibition	-	0.8344	83.44%
CYP2C19 inhibition	-	0.8517	85.17%
CYP2D6 inhibition	-	0.9091	90.91%
CYP1A2 inhibition	-	0.7473	74.73%
CYP2C8 inhibition	-	0.8573	85.73%
CYP inhibitory promiscuity	-	0.8430	84.30%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5815	58.15%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9428	94.28%
Skin irritation	-	0.7941	79.41%
Skin corrosion	-	0.9332	93.32%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5730	57.30%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.5699	56.99%
skin sensitisation	-	0.8455	84.55%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.5553	55.53%
Acute Oral Toxicity (c)	III	0.5997	59.97%
Estrogen receptor binding	+	0.6447	64.47%
Androgen receptor binding	-	0.5463	54.63%
Thyroid receptor binding	+	0.5873	58.73%
Glucocorticoid receptor binding	+	0.5493	54.93%
Aromatase binding	+	0.5422	54.22%
PPAR gamma	+	0.6519	65.19%
Honey bee toxicity	-	0.8499	84.99%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	-	0.4006	40.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.48%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.24%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.64%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.51%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.49%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.40%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.90%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.15%	89.00%
CHEMBL4208	P20618	Proteasome component C5	81.42%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	80.77%	94.73%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.65%	100.00%

Plants that contains it

• Brucea mollis

Cross-Links

• PubChem: 56833961
• LOTUS: LTS0114974
• wikiData: Q27137280