Bruceanic Acid A Methyl Ester

Details

• Internal ID: ec522391-0ce8-4215-90de-782ecf2cdff9
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: methyl 8-acetyl-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-11,12-dihydroxy-9-(2-methoxy-2-oxoethyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.01,6.02,13]pentadecane-13-carboxylate
• SMILES (Canonical): CC(C)C(=CC(=O)OC1C2C34COC2(C(C(C3C(C(CC4OC1=O)C(=O)C)(C)CC(=O)OC)O)O)C(=O)OC)C
• SMILES (Isomeric): CC(C)/C(=C/C(=O)OC1C2C34COC2(C(C(C3C(C(CC4OC1=O)C(=O)C)(C)CC(=O)OC)O)O)C(=O)OC)/C
• InChI: InChI=1S/C28H38O12/c1-12(2)13(3)8-17(30)40-20-22-27-11-38-28(22,25(35)37-7)23(33)19(32)21(27)26(5,10-18(31)36-6)15(14(4)29)9-16(27)39-24(20)34/h8,12,15-16,19-23,32-33H,9-11H2,1-7H3/b13-8+
• InChI Key: YGHOWFTZPVOCHA-MDWZMJQESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₁₂
• Molecular Weight: 566.60 g/mol
• Exact Mass: 566.23632664 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.50
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• 53663-08-4
• methyl 8-acetyl-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-11,12-dihydroxy-9-(2-methoxy-2-oxoethyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.01,6.02,13]pentadecane-13-carboxylate
• NSC238184
• BRUCEANTIN DECOMP. (B611103F121 AND K121)
• NSC 238184
• NSC-238184
• 3,10-Ethano-1H,8H-furo(3,4-d)(1)benzopyran-9-acetic acid, 8-acetyl-4-((3,4-dimethyl-1-oxo-2-pentenyl)oxy)octahydro-11,12-dihydroxy-3-(methoxycarbonyl)-9-methyl-5-oxo-, methyl ester, (3S-(3alpha,3aalpha,4alpha(E),6aalpha,8alpha,9beta,10alpha,10aS*,11S*,12R*))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9170	91.70%
Caco-2	-	0.7770	77.70%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8192	81.92%
OATP2B1 inhibitior	-	0.7195	71.95%
OATP1B1 inhibitior	+	0.8478	84.78%
OATP1B3 inhibitior	+	0.9284	92.84%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9223	92.23%
P-glycoprotein inhibitior	+	0.8098	80.98%
P-glycoprotein substrate	+	0.8427	84.27%
CYP3A4 substrate	+	0.6967	69.67%
CYP2C9 substrate	-	0.8253	82.53%
CYP2D6 substrate	-	0.8954	89.54%
CYP3A4 inhibition	-	0.8220	82.20%
CYP2C9 inhibition	-	0.8277	82.77%
CYP2C19 inhibition	-	0.8507	85.07%
CYP2D6 inhibition	-	0.9395	93.95%
CYP1A2 inhibition	-	0.8457	84.57%
CYP2C8 inhibition	+	0.4609	46.09%
CYP inhibitory promiscuity	-	0.8842	88.42%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5345	53.45%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9112	91.12%
Skin irritation	-	0.6188	61.88%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6351	63.51%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.5878	58.78%
skin sensitisation	-	0.8466	84.66%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6287	62.87%
Acute Oral Toxicity (c)	I	0.5678	56.78%
Estrogen receptor binding	+	0.7820	78.20%
Androgen receptor binding	+	0.6769	67.69%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7731	77.31%
Aromatase binding	+	0.6799	67.99%
PPAR gamma	+	0.6801	68.01%
Honey bee toxicity	-	0.5537	55.37%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9885	98.85%

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	99.42%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	98.22%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.24%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.25%	96.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	95.38%	89.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.28%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.95%	85.14%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	92.89%	96.47%
CHEMBL2581	P07339	Cathepsin D	92.10%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.35%	96.77%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	91.10%	95.71%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	90.73%	98.75%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.98%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.08%	92.62%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.62%	89.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.62%	95.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.05%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.00%	94.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.98%	97.28%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.35%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.21%	89.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.64%	95.71%
CHEMBL340	P08684	Cytochrome P450 3A4	83.64%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.61%	95.89%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.28%	92.88%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.02%	100.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.93%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.74%	99.23%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	81.87%	97.47%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.82%	96.38%
CHEMBL255	P29275	Adenosine A2b receptor	81.80%	98.59%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.36%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	80.04%	98.03%

Plants that contains it

• Brucea antidysenterica

Cross-Links

• PubChem: 5960381
• LOTUS: LTS0151352
• wikiData: Q105348092