Bruceolline B

Details

• Internal ID: c012e65a-91ee-43ea-aeba-26ba78f38ca0
• Taxonomy: Alkaloids and derivatives > Indolonaphthyridine alkaloids
• IUPAC Name: 3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
• SMILES (Canonical): C1=CC=C2C(=C1)C3=C4N2C(=O)C(=CC4=NC=C3)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C3=C4N2C(=O)C(=CC4=NC=C3)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O)O
• InChI: InChI=1S/C26H28N2O12/c29-8-15-18(30)20(32)22(34)25(39-15)37-9-16-19(31)21(33)23(35)26(40-16)38-14-7-12-17-11(5-6-27-12)10-3-1-2-4-13(10)28(17)24(14)36/h1-7,15-16,18-23,25-26,29-35H,8-9H2/t15-,16-,18-,19-,20+,21+,22-,23-,25-,26-/m1/s1
• InChI Key: VNELTEBGMWTQED-NXEOTYAVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈N₂O₁₂
• Molecular Weight: 560.50 g/mol
• Exact Mass: 560.16422433 g/mol
• Topological Polar Surface Area (TPSA): 213.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.56
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

• Bruceacanthinoside
• 159194-91-9
• 5-O-Glucopyranosyl-1-6-glucopyranosylcanthin-6-one
• 3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
• DTXSID40936071
• 6-Oxo-6H-indolo[3,2,1-de][1,5]naphthyridin-5-yl 6-O-hexopyranosylhexopyranoside
• 6H-Indolo(3,2,1-de)(1,5)naphthyridin-6-one, 5-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5798	57.98%
Caco-2	-	0.8823	88.23%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.4064	40.64%
OATP2B1 inhibitior	-	0.7076	70.76%
OATP1B1 inhibitior	+	0.9234	92.34%
OATP1B3 inhibitior	+	0.9423	94.23%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7257	72.57%
P-glycoprotein inhibitior	-	0.6086	60.86%
P-glycoprotein substrate	-	0.6692	66.92%
CYP3A4 substrate	+	0.6473	64.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8610	86.10%
CYP3A4 inhibition	-	0.8512	85.12%
CYP2C9 inhibition	-	0.8753	87.53%
CYP2C19 inhibition	-	0.8426	84.26%
CYP2D6 inhibition	-	0.8609	86.09%
CYP1A2 inhibition	+	0.5406	54.06%
CYP2C8 inhibition	+	0.6494	64.94%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6163	61.63%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9417	94.17%
Skin irritation	-	0.8064	80.64%
Skin corrosion	-	0.9476	94.76%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6599	65.99%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.5460	54.60%
skin sensitisation	-	0.8885	88.85%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7267	72.67%
Acute Oral Toxicity (c)	III	0.5375	53.75%
Estrogen receptor binding	+	0.7249	72.49%
Androgen receptor binding	+	0.5786	57.86%
Thyroid receptor binding	+	0.6356	63.56%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.7125	71.25%
PPAR gamma	+	0.7511	75.11%
Honey bee toxicity	-	0.8313	83.13%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.5935	59.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.91%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.64%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.36%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.84%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.23%	85.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	93.03%	95.83%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.99%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.97%	95.56%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	91.73%	96.47%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.39%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.40%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	87.64%	91.49%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.42%	97.36%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.33%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.27%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.55%	99.17%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	81.25%	88.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.17%	94.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.47%	94.62%

Plants that contains it

• Asplenium normale
• Brucea javanica
• Brucea mollis
• Carpobrotus edulis
• Castanea crenata
• Centrolobium tomentosum
• Ceratophyllum submersum
• Dracocephalum kotschyi
• Lippia carviodora
• Myrica nana
• Psilostrophe cooperi
• Sideritis tragoriganum
• Solanum jamaicense
• Trifolium alexandrinum

Cross-Links

• PubChem: 190940
• NPASS: NPC37685
• LOTUS: LTS0145152
• wikiData: Q82912213