Bruceine E

Details

• Internal ID: c3db9caa-3ed5-480b-b079-d6db66dd2923
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: (1R,2R,3R,6R,8S,11S,12S,13S,14R,15R,16S,17R)-2,3,11,12,15,16-hexahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-en-4-one
• SMILES (Canonical): CC1=CC(C(C2(C1CC3C45C2C(C(C(C4(C(C(=O)O3)O)O)(OC5)C)O)O)C)O)O
• SMILES (Isomeric): CC1=C[C@@H]([C@H]([C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@]4([C@H](C(=O)O3)O)O)(OC5)C)O)O)C)O)O
• InChI: InChI=1S/C20H28O9/c1-7-4-9(21)13(23)17(2)8(7)5-10-19-6-28-18(3,14(24)11(22)12(17)19)20(19,27)15(25)16(26)29-10/h4,8-15,21-25,27H,5-6H2,1-3H3/t8-,9-,10+,11+,12+,13+,14-,15-,17-,18+,19+,20+/m0/s1
• InChI Key: ZBXITHPYBBXZRG-QYUWQHSUSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₉
• Molecular Weight: 412.40 g/mol
• Exact Mass: 412.17333247 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: -2.80
• Atomic LogP (AlogP): -2.16
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 0

Synonyms

• 21586-90-3
• CHEMBL2037038
• (1R,2R,3R,6R,8S,11S,12S,13S,14R,15R,16S,17R)-2,3,11,12,15,16-hexahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-en-4-one
• HY-N3015
• AKOS040760152
• CS-0022970

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8820	88.20%
Caco-2	-	0.7692	76.92%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7235	72.35%
OATP2B1 inhibitior	-	0.8617	86.17%
OATP1B1 inhibitior	+	0.8706	87.06%
OATP1B3 inhibitior	+	0.9640	96.40%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6452	64.52%
P-glycoprotein inhibitior	-	0.8313	83.13%
P-glycoprotein substrate	+	0.5405	54.05%
CYP3A4 substrate	+	0.6480	64.80%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8526	85.26%
CYP3A4 inhibition	-	0.9205	92.05%
CYP2C9 inhibition	-	0.9014	90.14%
CYP2C19 inhibition	-	0.8834	88.34%
CYP2D6 inhibition	-	0.9374	93.74%
CYP1A2 inhibition	-	0.8409	84.09%
CYP2C8 inhibition	-	0.8035	80.35%
CYP inhibitory promiscuity	-	0.9013	90.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5683	56.83%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9581	95.81%
Skin irritation	-	0.5860	58.60%
Skin corrosion	-	0.9201	92.01%
Ames mutagenesis	-	0.7264	72.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.5946	59.46%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5339	53.39%
skin sensitisation	-	0.8409	84.09%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.8165	81.65%
Acute Oral Toxicity (c)	III	0.5795	57.95%
Estrogen receptor binding	+	0.8101	81.01%
Androgen receptor binding	+	0.6904	69.04%
Thyroid receptor binding	+	0.5969	59.69%
Glucocorticoid receptor binding	+	0.6647	66.47%
Aromatase binding	+	0.6286	62.86%
PPAR gamma	+	0.6161	61.61%
Honey bee toxicity	-	0.7366	73.66%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9482	94.82%

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	96.02%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.39%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.32%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.39%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.80%	100.00%
CHEMBL2581	P07339	Cathepsin D	86.17%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.96%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.71%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.89%	97.09%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.50%	90.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.37%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.70%	86.33%

Plants that contains it

• Asplenium normale
• Brucea javanica
• 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: 5315510
• NPASS: NPC176513
• ChEMBL: CHEMBL2037038
• LOTUS: LTS0043116
• wikiData: Q105370892