Bruceantin

Details

• Internal ID: dadba60f-ca34-4528-b5a6-b06dbfddffbe
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-[(E)-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-carboxylate
• SMILES (Canonical): CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(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(C)C)(OC5)C(=O)OC)O)O)C)O
• InChI: InChI=1S/C28H36O11/c1-11(2)12(3)7-17(30)39-20-22-27-10-37-28(22,25(35)36-6)23(33)19(32)21(27)26(5)9-15(29)18(31)13(4)14(26)8-16(27)38-24(20)34/h7,11,14,16,19-23,31-33H,8-10H2,1-6H3/b12-7+/t14-,16+,19+,20+,21+,22+,23-,26-,27+,28-/m0/s1
• InChI Key: IRQXZTBHNKVIRL-GOTQHHPNSA-N
• Popularity: 45 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₆O₁₁
• Molecular Weight: 548.60 g/mol
• Exact Mass: 548.22576196 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.15
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 41451-75-6
• Bruceantine
• NSC-165563
• UNII-S3NW88DI4T
• Bruceantin(NSC165563)
• S3NW88DI4T
• MLS002703020
• CHEBI:3188
• NSC 165563
• NSC165563
• Picras-3-en-21-oic acid, 15-((3,4-dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-3,11,12-trihydroxy-2,16-dioxo-, methyl ester, (11beta,12alpha,15beta(E))- (9CI)
• C28-H36-O11
• Picras-3-en-21-oic acid,4-dimethyl-1-oxo-2-pentenyl)oxy]-13,20-epoxy-3,11,12-trihydroxy-2,16-dioxo-, methyl ester, (11.beta.,12.alpha.,15.beta.(E))-
• Picras-3-en-21-oic acid,4-dimethyl-1-oxo-2-pentenyl)oxy]-13,20-epoxy-3,11,12-trihydroxy-2,16-dioxo-, methyl ester, [11.beta.,12.alpha.,15.beta.(E)]-
• BRUCEANTIN [MI]
• CHEMBL509895
• SCHEMBL16742407
• 2H-3,11c-(Epoxymethano)phenanthro(10,1-bc)pyran, picras-3-en-21-oic acid deriv.
• 2H-3,11c-(Epoxymethano)phenanthro[10,1-bc]pyran, picras-3-en-21-oic acid deriv.
• IRQXZTBHNKVIRL-GOTQHHPNSA-N
• HY-N0840
• Picras-3-en-21-oic acid, 15-((3,4-dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-3,11,12-trihydroxy-2,16-dioxo-, methyl ester, (11beta,12alpha,15beta(E))-
• MFCD00866510
• NCI-165563
• MS-30048
• C08749
• A873054
• 2H-3,1-bc]pyran, picras-3-en-21-oic acid deriv.
• Q27105979
• 2H-3,11c-(Epoxymethano)phenanthro[10,1-bc]pyran, picras-3-en-21-oic acid deriv
• methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-[(E)-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-carboxylate
• PICRAS-3-EN-21-OIC ACID, 15-(((2E)-3,4-DIMETHYL-1-OXO-2-PENTEN-1-YL)OXY)-13,20-EPOXY-3,11,12-TRIHYDROXY-2,16-DIOXO-, METHYL ESTER, (11.BETA.,12.ALPHA.,15.BETA.)-
• Picras-3-en-21-oic acid,4-dimethyl-1-oxo-2-pentenyl)oxy]-13,20-epoxy-3,11,12-trihydroxy-2,16-dioxo-, methyl ester [11.beta.,12.alpha.,15.beta.(E]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9461	94.61%
Caco-2	-	0.7924	79.24%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8150	81.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8541	85.41%
OATP1B3 inhibitior	+	0.9194	91.94%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8887	88.87%
P-glycoprotein inhibitior	+	0.7320	73.20%
P-glycoprotein substrate	+	0.8913	89.13%
CYP3A4 substrate	+	0.7072	70.72%
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	+	0.4722	47.22%
CYP inhibitory promiscuity	-	0.9291	92.91%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5617	56.17%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9146	91.46%
Skin irritation	-	0.6481	64.81%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6224	62.24%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8465	84.65%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.6946	69.46%
Acute Oral Toxicity (c)	I	0.4133	41.33%
Estrogen receptor binding	+	0.7744	77.44%
Androgen receptor binding	+	0.7013	70.13%
Thyroid receptor binding	+	0.5173	51.73%
Glucocorticoid receptor binding	+	0.7997	79.97%
Aromatase binding	+	0.7544	75.44%
PPAR gamma	+	0.7018	70.18%
Honey bee toxicity	-	0.5000	50.00%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9895	98.95%

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	99.57%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	99.46%	83.82%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.38%	96.77%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	95.16%	96.47%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.11%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.10%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.98%	94.45%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	94.56%	97.47%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	94.49%	95.71%
CHEMBL2581	P07339	Cathepsin D	94.17%	98.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	93.99%	89.34%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.75%	96.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	92.34%	91.07%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	90.11%	98.75%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.95%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.43%	95.56%
CHEMBL299	P17252	Protein kinase C alpha	87.97%	98.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.17%	89.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.63%	96.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.39%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.10%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.07%	96.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.34%	94.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.31%	97.28%
CHEMBL340	P08684	Cytochrome P450 3A4	85.23%	91.19%
CHEMBL1937	Q92769	Histone deacetylase 2	85.19%	94.75%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.92%	89.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.74%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.13%	97.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.97%	97.21%
CHEMBL5028	O14672	ADAM10	81.71%	97.50%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.23%	90.93%
CHEMBL2996	Q05655	Protein kinase C delta	80.42%	97.79%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.23%	91.24%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.16%	92.62%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.12%	93.04%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.06%	95.89%

Plants that contains it

• Asplenium normale
• Brucea antidysenterica
• 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: 5281304
• NPASS: NPC265557
• ChEMBL: CHEMBL509895
• LOTUS: LTS0019470
• wikiData: Q27105979