Brusatol

Details

• Internal ID: 07f93e31-e602-43d8-84de-d4d3616b9fbd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-10,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
• SMILES (Canonical): CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C)(OC5)C(=O)OC)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)(OC5)C(=O)OC)O)O)C)O
• InChI: InChI=1S/C26H32O11/c1-10(2)6-15(28)37-18-20-25-9-35-26(20,23(33)34-5)21(31)17(30)19(25)24(4)8-13(27)16(29)11(3)12(24)7-14(25)36-22(18)32/h6,12,14,17-21,29-31H,7-9H2,1-5H3/t12-,14+,17+,18+,19+,20+,21-,24-,25+,26-/m0/s1
• InChI Key: ZZZYHIMVKOHVIH-VILODJCFSA-N
• Popularity: 97 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₁
• Molecular Weight: 520.50 g/mol
• Exact Mass: 520.19446183 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.52
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• Yatansin
• 14907-98-3
• (+)-Brusatol
• NSC 172924
• CHEBI:3197
• BRN 1444847
• CHEMBL459546
• Methyl 13,20-epoxy-3,11,12-trihydroxy-15-((3-methyl-1-oxo-2-butenyl)oxy)-2,16-dioxopicras-3-en-21-oate (11beta,12alpha,15beta)-
• (11beta,12alpha,15beta)-13,20-Epoxy-3,11,12-trihydroxy-15-((3-methyl-1-oxo-2-butenyl)oxy)-2,16-dioxopicras-3-en-21-oic acid, methyl ester
• (1R,2S,3S,3aS,3a1R,4R,6aR,7aR,11aS,11bR)-Methyl 1,2,9-trihydroxy-8,11a-dimethyl-4-((3-methylbut-2-enoyl)oxy)-5,10-dioxo-2,3,3a,4,5,6a,7,7a,10,11,11a,11b-dodecahydro-1H-3,3a1-(epoxymethano)dibenzo[de,g]chromene-3-carboxylate
• 2H-3,11c-beta-(Epoxymethano)phenanthro(10,1-bc)pyran-3-alpha(3a-beta-H)-carboxylic acid, 1,4,5,6a-beta,7,7a-alpha,10,11,11a,11b-alpha-decahydro-8,11a-beta-dimethyl-5,10-dioxo-1-beta,2-alpha,4-beta,9-tetrahydroxy-, methyl ester, 4-(3-methylcrotonate)
• Picras-3-en-21-oic acid, 13,20-epoxy-3,11,12-trihydroxy-15-((3-methyl-1-oxo-2-butenyl)oxy)-2,16-dioxo-, methyl ester, (11beta,12alpha,15beta)-
• NSC-172924
• 3ATY6SZ64B
• SCHEMBL1276480
• Brusatol, >=95% (HPLC)
• DTXSID70164163
• GLXC-16649
• BCP15272
• methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-10,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
• BDBM50535743
• MFCD01746220
• AKOS016013415
• CS-W019658
• AS-55977
• HY-19543
• LS-64076
• C08754
• Q27105985
• methyl trihydroxy-dimethyl-(3-methylbut-2-enoyloxy)-dioxo-[?]carboxylate
• (1R,2S,3S,3aS,3a1R,4R,6aR,7aR,11aS,11bR)-Methyl1,2,9-trihydroxy-8,11a-dimethyl-4-((3-methylbut-2-enoyl)oxy)-5,10-dioxo-2,3,3a,4,5,6a,7,7a,10,11,11a,11b-dodecahydro-1H-3,3a1-(epoxymethano)dibenzo[de,g]chromene-3-carboxylate
• 2H-3,11cbeta-(Epoxymethano)phenanthro[10,1-bc]pyran-3alpha(3abetaH)-carboxylic acid, 1,4,5,6abeta,7,7aalpha,10,11,11a,11balpha-decahydro-1beta,2alpha,4beta,9-tetrahydroxy-8,11abeta-dimethyl-5,10-dioxo-, methyl ester, 4-(3-methylcrotonate)
• Crotonic acid, 3-methyl-, 4-ester with methyl 1,4,5,6abeta,7,7aalpha,10,11,11a,11balpha-decahydro-1beta,2alpha,4beta,9-tetrahydroxy-8,11abeta-dimethyl-5,10-dioxo-2H-3,11cbeta-(epoxymethano)phenanthro[10,1-bc]pyran-3alpha(3abetaH)-carboxylate
• Picras-3-en-21-oic acid, 13,20-epoxy-3,11,12-trihydroxy-15-[(3-methyl-1-oxo-2-buten-1-yl)oxy]-2,16-dioxo-, methyl ester, (11beta,12alpha,15beta)-
• Picras-3-en-21-oicacid,13,20-epoxy-3,11,12-trihydroxy-15-[(3-methyl-1-oxo-2-buten-1-yl)oxy]-2,16-dioxo-,methyl ester, (11b,12a,15b)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9461	94.61%
Caco-2	-	0.7850	78.50%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8150	81.50%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8646	86.46%
OATP1B3 inhibitior	+	0.9194	91.94%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9434	94.34%
P-glycoprotein inhibitior	+	0.6796	67.96%
P-glycoprotein substrate	+	0.9097	90.97%
CYP3A4 substrate	+	0.7058	70.58%
CYP2C9 substrate	-	0.8217	82.17%
CYP2D6 substrate	-	0.8917	89.17%
CYP3A4 inhibition	-	0.7852	78.52%
CYP2C9 inhibition	-	0.7951	79.51%
CYP2C19 inhibition	-	0.8467	84.67%
CYP2D6 inhibition	-	0.9413	94.13%
CYP1A2 inhibition	-	0.8327	83.27%
CYP2C8 inhibition	+	0.4751	47.51%
CYP inhibitory promiscuity	-	0.9291	92.91%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5617	56.17%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9038	90.38%
Skin irritation	-	0.6481	64.81%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5172	51.72%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8465	84.65%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.7826	78.26%
Acute Oral Toxicity (c)	I	0.4133	41.33%
Estrogen receptor binding	+	0.7690	76.90%
Androgen receptor binding	+	0.6936	69.36%
Thyroid receptor binding	-	0.4934	49.34%
Glucocorticoid receptor binding	+	0.7945	79.45%
Aromatase binding	+	0.7412	74.12%
PPAR gamma	+	0.6981	69.81%
Honey bee toxicity	-	0.5211	52.11%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9895	98.95%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	29.19 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.71%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.98%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.87%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.46%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.44%	96.77%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	91.56%	89.34%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	91.00%	91.07%
CHEMBL2581	P07339	Cathepsin D	90.95%	98.95%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	90.54%	97.47%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.21%	94.45%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	89.16%	95.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.75%	89.00%
CHEMBL299	P17252	Protein kinase C alpha	88.18%	98.03%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.55%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.14%	95.56%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.47%	97.28%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.38%	99.23%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.06%	94.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.22%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	85.14%	91.19%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.69%	90.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.36%	95.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.71%	93.03%
CHEMBL5028	O14672	ADAM10	83.36%	97.50%
CHEMBL2243	O00519	Anandamide amidohydrolase	83.36%	97.53%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.69%	93.04%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.21%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.80%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.55%	95.50%
CHEMBL2996	Q05655	Protein kinase C delta	80.54%	97.79%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	80.48%	97.88%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.37%	96.38%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.14%	97.14%

Plants that contains it

• Asplenium normale
• Brucea javanica
• Brucea mollis
• 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: 73432
• NPASS: NPC152301
• LOTUS: LTS0180340
• wikiData: Q27105985