Bruceoside-F

Details

• Internal ID: 29c77821-b4f4-4468-83c0-19e81ee0f379
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: (1R,2S,3R,6R,8S,9S,13S,14R,15R,16S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-11-ene-17-carboxylic acid
• SMILES (Canonical): CC1C2CC3C45COC(C4C(C(=O)O3)OC(=O)C=C(C)C(C)(C)OC(=O)C)(C(C(C5C2(C=C(C1=O)OC6C(C(C(C(O6)CO)O)O)O)C)O)O)C(=O)O
• SMILES (Isomeric): C[C@H]1[C@@H]2C[C@@H]3[C@@]45COC([C@@H]4[C@H](C(=O)O3)OC(=O)/C=C(\C)/C(C)(C)OC(=O)C)([C@H]([C@@H]([C@@H]5[C@]2(C=C(C1=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)O)O)C(=O)O
• InChI: InChI=1S/C35H46O18/c1-12(32(4,5)53-14(3)37)7-19(38)52-25-27-34-11-48-35(27,31(46)47)28(44)24(43)26(34)33(6)9-16(20(39)13(2)15(33)8-18(34)51-29(25)45)49-30-23(42)22(41)21(40)17(10-36)50-30/h7,9,13,15,17-18,21-28,30,36,40-44H,8,10-11H2,1-6H3,(H,46,47)/b12-7+/t13-,15-,17+,18+,21+,22-,23+,24+,25+,26+,27+,28-,30+,33-,34+,35?/m0/s1
• InChI Key: HLVUVKGKEFOUCN-QQBCAOPKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₆O₁₈
• Molecular Weight: 754.70 g/mol
• Exact Mass: 754.26841461 g/mol
• Topological Polar Surface Area (TPSA): 282.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -2.14
• H-Bond Acceptor: 17
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• Bruceoside F
• (+)-Bruceoside F
• 167782-24-3
• (1R,2S,3R,6R,8S,9S,13S,14R,15R,16S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-11-ene-17-carboxylic acid
• Picras-1-en-21-oic acid, 15-((4-(acetyloxy)-3,4-dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-2-(beta-D-glucopyranosyloxy)-11,12-dihydroxy-3,16-dioxo-, (11beta,12alpha,15beta(E))-
• [(E)-4-acetoxy-3,4-dimethyl-pent-2-enoyl]oxy-dihydroxy-dimethyl-dioxo-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-[?]carboxylic acid
• Picras-1-en-21-oic acid, 15-[[4-(acetyloxy)-3,4-dimethyl-1-oxo-2-pentenyl]oxy]-13,20-epoxy-2-(.beta.-D-glucopyranosyloxy)-11,12-dihydroxy-3,16-dioxo-, [11.beta.,12.alpha.,15.beta.(E)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7113	71.13%
Caco-2	-	0.8716	87.16%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7832	78.32%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.8176	81.76%
OATP1B3 inhibitior	+	0.9267	92.67%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7872	78.72%
P-glycoprotein inhibitior	+	0.7406	74.06%
P-glycoprotein substrate	+	0.7245	72.45%
CYP3A4 substrate	+	0.7240	72.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8904	89.04%
CYP3A4 inhibition	-	0.9007	90.07%
CYP2C9 inhibition	-	0.8272	82.72%
CYP2C19 inhibition	-	0.8543	85.43%
CYP2D6 inhibition	-	0.9341	93.41%
CYP1A2 inhibition	-	0.8829	88.29%
CYP2C8 inhibition	+	0.7014	70.14%
CYP inhibitory promiscuity	-	0.8456	84.56%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6074	60.74%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9113	91.13%
Skin irritation	-	0.6909	69.09%
Skin corrosion	-	0.9328	93.28%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4019	40.19%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8500	85.00%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6488	64.88%
Acute Oral Toxicity (c)	III	0.6314	63.14%
Estrogen receptor binding	+	0.8037	80.37%
Androgen receptor binding	+	0.7410	74.10%
Thyroid receptor binding	+	0.5249	52.49%
Glucocorticoid receptor binding	+	0.7776	77.76%
Aromatase binding	+	0.6957	69.57%
PPAR gamma	+	0.7605	76.05%
Honey bee toxicity	-	0.6269	62.69%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9520	95.20%

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	98.72%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.88%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.44%	85.14%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	95.17%	89.34%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.86%	86.33%
CHEMBL2581	P07339	Cathepsin D	94.49%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.48%	96.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.47%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.37%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.23%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	88.15%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.12%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	87.36%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.90%	97.09%
CHEMBL5028	O14672	ADAM10	83.94%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.81%	91.07%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.60%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.95%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.87%	99.23%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.21%	97.28%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.70%	95.71%

Plants that contains it

• Brucea javanica

Cross-Links

• PubChem: 6451123
• LOTUS: LTS0208541
• wikiData: Q105030339