Bruceajavanin A

Details

• Internal ID: 8ddefb4d-0b8d-4e71-9549-88687d9236ab
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(5R,7R,8R,9R,10R,13S,17S)-17-[(2R,3S,5R)-2-acetyloxy-5-[(2S)-3,3-dimethyloxiran-2-yl]oxolan-3-yl]-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC2C(C(=O)C=CC2(C3C1(C4=CCC(C4(CC3)C)C5CC(OC5OC(=O)C)C6C(O6)(C)C)C)C)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@](C=CC(=O)C2(C)C)([C@@H]3[C@@]1(C4=CC[C@H]([C@@]4(CC3)C)[C@@H]5C[C@@H](O[C@@H]5OC(=O)C)[C@H]6C(O6)(C)C)C)C
• InChI: InChI=1S/C34H48O7/c1-18(35)38-27-17-25-30(3,4)26(37)13-15-33(25,8)24-12-14-32(7)21(10-11-23(32)34(24,27)9)20-16-22(28-31(5,6)41-28)40-29(20)39-19(2)36/h11,13,15,20-22,24-25,27-29H,10,12,14,16-17H2,1-9H3/t20-,21-,22+,24+,25-,27+,28-,29-,32-,33+,34-/m0/s1
• InChI Key: ZTCBOAIWPIKLEJ-DAMXAWHRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₈O₇
• Molecular Weight: 568.70 g/mol
• Exact Mass: 568.34000387 g/mol
• Topological Polar Surface Area (TPSA): 91.40 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 5.95
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 161043-66-9
• [(5R,7R,8R,9R,10R,13S,17S)-17-[(2R,3S,5R)-2-acetyloxy-5-[(2S)-3,3-dimethyloxiran-2-yl]oxolan-3-yl]-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-yl] acetate
• Cholesta-1,14-dien-3-one, 7,21-bis(acetyloxy)-21,23:24,25-diepoxy-4,4,8-trimethyl-, (5alpha,7alpha,13alpha,17alpha,20S,21R,23R,24S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9934	99.34%
Caco-2	-	0.7534	75.34%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8110	81.10%
OATP2B1 inhibitior	-	0.8626	86.26%
OATP1B1 inhibitior	+	0.7803	78.03%
OATP1B3 inhibitior	+	0.8041	80.41%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9214	92.14%
P-glycoprotein inhibitior	+	0.8253	82.53%
P-glycoprotein substrate	-	0.5460	54.60%
CYP3A4 substrate	+	0.7421	74.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8875	88.75%
CYP3A4 inhibition	-	0.5425	54.25%
CYP2C9 inhibition	-	0.7603	76.03%
CYP2C19 inhibition	-	0.8218	82.18%
CYP2D6 inhibition	-	0.9418	94.18%
CYP1A2 inhibition	-	0.7550	75.50%
CYP2C8 inhibition	+	0.6802	68.02%
CYP inhibitory promiscuity	-	0.8079	80.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4503	45.03%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.9177	91.77%
Skin irritation	-	0.5885	58.85%
Skin corrosion	-	0.8996	89.96%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7053	70.53%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.7976	79.76%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7050	70.50%
Acute Oral Toxicity (c)	III	0.4210	42.10%
Estrogen receptor binding	+	0.7922	79.22%
Androgen receptor binding	+	0.7089	70.89%
Thyroid receptor binding	+	0.6167	61.67%
Glucocorticoid receptor binding	+	0.7355	73.55%
Aromatase binding	+	0.6840	68.40%
PPAR gamma	+	0.7441	74.41%
Honey bee toxicity	-	0.7230	72.30%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9969	99.69%

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	96.01%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.45%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.10%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.90%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.53%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.54%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	89.14%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.75%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.92%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.29%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.65%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.64%	82.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.12%	97.14%
CHEMBL5028	O14672	ADAM10	82.73%	97.50%
CHEMBL1937	Q92769	Histone deacetylase 2	82.46%	94.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.25%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.63%	92.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.56%	97.25%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.81%	97.28%

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: 10030889
• NPASS: NPC61694
• LOTUS: LTS0252530
• wikiData: Q105382837