Bruceanic acid D

Details

• Internal ID: 6d0ea38e-a848-4a1a-a0a5-71610ef303ca
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: methyl (11S,12R,13S)-8-acetyl-11,12-dihydroxy-3-[(E)-4-hydroxy-3,4-dimethylpent-2-enoyl]oxy-9-(2-methoxy-2-oxoethyl)-4-oxo-5,14-dioxatetracyclo[8.5.0.01,6.02,13]pentadecane-13-carboxylate
• SMILES (Canonical): CC(=CC(=O)OC1C2C34COC2(C(C(C3C(C(CC4OC1=O)C(=O)C)CC(=O)OC)O)O)C(=O)OC)C(C)(C)O
• SMILES (Isomeric): C/C(=C\C(=O)OC1C2[C@]3([C@@H]([C@H](C4C2(CO3)C(CC(C4CC(=O)OC)C(=O)C)OC1=O)O)O)C(=O)OC)/C(C)(C)O
• InChI: InChI=1S/C27H36O13/c1-11(25(3,4)35)7-17(30)40-20-21-26-10-38-27(21,24(34)37-6)22(32)19(31)18(26)14(9-16(29)36-5)13(12(2)28)8-15(26)39-23(20)33/h7,13-15,18-22,31-32,35H,8-10H2,1-6H3/b11-7+/t13?,14?,15?,18?,19-,20?,21?,22+,26?,27-/m0/s1
• InChI Key: FKCBKHBQLCJMBJ-USLLDNLKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₆O₁₃
• Molecular Weight: 568.60 g/mol
• Exact Mass: 568.21559120 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.77
• H-Bond Acceptor: 13
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

• 132587-61-2
• 3,10-Ethano-1H,8H-furo(3,4-d)(1)benzopyran-9-acetic acid, 8-acetyloctahydro-11,12-dihydroxy-4-((4-hydroxy-3,4-dimethyl-1-oxo-2-pentenyl)oxy)-3-(methoxycarbonyl)-9-methyl-5-oxo-, (3S-(3alpha,3aalpha,4alpha(E),6aalpha,8alpha,9beta,10alpha,10aS,11S*,12R*))-
• Methyl (11S,12R,13S)-8-acetyl-11,12-dihydroxy-3-[(E)-4-hydroxy-3,4-dimethylpent-2-enoyl]oxy-9-(2-methoxy-2-oxoethyl)-4-oxo-5,14-dioxatetracyclo[8.5.0.01,6.02,13]pentadecane-13-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8986	89.86%
Caco-2	-	0.7971	79.71%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8349	83.49%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8322	83.22%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9259	92.59%
P-glycoprotein inhibitior	+	0.7735	77.35%
P-glycoprotein substrate	+	0.8061	80.61%
CYP3A4 substrate	+	0.6946	69.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8999	89.99%
CYP3A4 inhibition	-	0.8722	87.22%
CYP2C9 inhibition	-	0.8477	84.77%
CYP2C19 inhibition	-	0.8435	84.35%
CYP2D6 inhibition	-	0.9318	93.18%
CYP1A2 inhibition	-	0.8547	85.47%
CYP2C8 inhibition	+	0.5961	59.61%
CYP inhibitory promiscuity	-	0.8751	87.51%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5545	55.45%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9152	91.52%
Skin irritation	-	0.6460	64.60%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6789	67.89%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.6199	61.99%
skin sensitisation	-	0.8293	82.93%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.7958	79.58%
Acute Oral Toxicity (c)	I	0.4908	49.08%
Estrogen receptor binding	+	0.7280	72.80%
Androgen receptor binding	+	0.7168	71.68%
Thyroid receptor binding	-	0.5129	51.29%
Glucocorticoid receptor binding	+	0.7579	75.79%
Aromatase binding	+	0.6660	66.60%
PPAR gamma	+	0.6516	65.16%
Honey bee toxicity	-	0.6042	60.42%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9781	97.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.10%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.97%	91.11%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	96.43%	89.34%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.41%	85.14%
CHEMBL3922	P50579	Methionine aminopeptidase 2	92.84%	97.28%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.36%	96.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.49%	91.07%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.56%	96.77%
CHEMBL2581	P07339	Cathepsin D	88.76%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	88.50%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.37%	94.45%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.21%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.99%	89.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	86.31%	95.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.75%	95.56%
CHEMBL5028	O14672	ADAM10	84.54%	97.50%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.51%	90.93%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.04%	91.24%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.65%	89.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.95%	99.23%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.81%	96.90%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	82.41%	80.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.22%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.07%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.61%	100.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.96%	97.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.68%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.60%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.22%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.13%	97.14%

Plants that contains it

• Brucea antidysenterica

Cross-Links

• PubChem: 6439339
• LOTUS: LTS0103743
• wikiData: Q105105169