Bruceantinol A

Details

• Internal ID: 26161b30-fe5d-485c-a0e4-adb80c0595c3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylic acid
• SMILES (Canonical): CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C(C)(C)OC(=O)C)(OC5)C(=O)O)O)O)C)O
• SMILES (Isomeric): CC1=C(C(=O)C[C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@H]4[C@H](C(=O)O3)OC(=O)/C=C(\C)/C(C)(C)OC(=O)C)(OC5)C(=O)O)O)O)C)O
• InChI: InChI=1S/C29H36O13/c1-11(26(4,5)42-13(3)30)7-17(32)41-20-22-28-10-39-29(22,25(37)38)23(35)19(34)21(28)27(6)9-15(31)18(33)12(2)14(27)8-16(28)40-24(20)36/h7,14,16,19-23,33-35H,8-10H2,1-6H3,(H,37,38)/b11-7+/t14-,16+,19+,20+,21+,22+,23-,27-,28+,29-/m0/s1
• InChI Key: HPJCIKYCFBCHLF-IVOVFOCPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₃
• Molecular Weight: 592.60 g/mol
• Exact Mass: 592.21559120 g/mol
• Topological Polar Surface Area (TPSA): 203.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.75
• H-Bond Acceptor: 12
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 948038-36-6
• CHEMBL251342
• HY-N10897
• AKOS040763624
• CS-0637353
• (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8993	89.93%
Caco-2	-	0.8373	83.73%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8135	81.35%
OATP2B1 inhibitior	-	0.7193	71.93%
OATP1B1 inhibitior	+	0.8430	84.30%
OATP1B3 inhibitior	+	0.9205	92.05%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8899	88.99%
P-glycoprotein inhibitior	+	0.7219	72.19%
P-glycoprotein substrate	+	0.8247	82.47%
CYP3A4 substrate	+	0.7181	71.81%
CYP2C9 substrate	-	0.8191	81.91%
CYP2D6 substrate	-	0.8935	89.35%
CYP3A4 inhibition	-	0.8683	86.83%
CYP2C9 inhibition	-	0.7973	79.73%
CYP2C19 inhibition	-	0.8751	87.51%
CYP2D6 inhibition	-	0.9396	93.96%
CYP1A2 inhibition	-	0.8667	86.67%
CYP2C8 inhibition	+	0.6072	60.72%
CYP inhibitory promiscuity	-	0.9039	90.39%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5995	59.95%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9134	91.34%
Skin irritation	-	0.6210	62.10%
Skin corrosion	-	0.9351	93.51%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5652	56.52%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.5879	58.79%
skin sensitisation	-	0.8505	85.05%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.8543	85.43%
Acute Oral Toxicity (c)	III	0.4965	49.65%
Estrogen receptor binding	+	0.7557	75.57%
Androgen receptor binding	+	0.7225	72.25%
Thyroid receptor binding	-	0.4905	49.05%
Glucocorticoid receptor binding	+	0.7966	79.66%
Aromatase binding	+	0.7547	75.47%
PPAR gamma	+	0.6888	68.88%
Honey bee toxicity	-	0.5686	56.86%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9932	99.32%

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	97.52%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.50%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.24%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.94%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	91.06%	89.34%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.83%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.51%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.95%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.78%	86.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.11%	96.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.85%	96.77%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.80%	93.04%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.77%	91.07%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	87.55%	97.47%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.11%	96.00%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	86.85%	90.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.71%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.85%	95.89%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.17%	96.47%
CHEMBL299	P17252	Protein kinase C alpha	84.14%	98.03%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	84.12%	97.88%
CHEMBL5028	O14672	ADAM10	84.02%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	83.33%	91.19%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.77%	97.28%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.34%	93.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.32%	89.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.65%	96.21%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.53%	95.71%
CHEMBL2996	Q05655	Protein kinase C delta	80.36%	97.79%

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: 23656477
• NPASS: NPC91693
• LOTUS: LTS0159157
• wikiData: Q105031720