bruguierins A

Details

• Internal ID: 9be38ef0-c7c5-494b-b0d8-7fd69560093d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(1R,3S,5S,8R,9S,10R,13R,14R,17S)-1-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] octadecanoate
• SMILES (Canonical): CCCCCCCCCCCCCCCCCC(=O)OC1CC(C2(C3CCC4C(CCC4(C3(CCC2C1(C)C)C)C)C(C)(CCC=C(C)C)O)C)O
• SMILES (Isomeric): CCCCCCCCCCCCCCCCCC(=O)O[C@H]1C[C@H]([C@@]2([C@H]3CC[C@@H]4[C@H](CC[C@]4([C@@]3(CC[C@H]2C1(C)C)C)C)[C@](C)(CCC=C(C)C)O)C)O
• InChI: InChI=1S/C48H86O4/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-27-43(50)52-42-35-41(49)48(9)39(44(42,4)5)31-34-46(7)40(48)29-28-37-38(30-33-45(37,46)6)47(8,51)32-25-26-36(2)3/h26,37-42,49,51H,10-25,27-35H2,1-9H3/t37-,38+,39+,40+,41-,42+,45-,46-,47+,48+/m1/s1
• InChI Key: BCRQTNOYBAWCDF-XRYSTRTLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₈₆O₄
• Molecular Weight: 727.20 g/mol
• Exact Mass: 726.65261122 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 16.60
• Atomic LogP (AlogP): 13.31
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 21

Synonyms

• bruguierins A
• BDBM50259771
• 1beta,20-(S)-dihydroxydammar-24(25)-ene-3beta-O-stearate
• InChI=1/C48H86O4/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-27-43(50)52-42-35-41(49)48(9)39(44(42,4)5)31-34-46(7)40(48)29-28-37-38(30-33-45(37,46)6)47(8,51)32-25-26-36(2)3/h26,37-42,49,51H,10-25,27-35H2,1-9H3/t37-,38+,39+,40+,41?,42?,45-,46-,47+,48+

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9967	99.67%
Caco-2	-	0.8250	82.50%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7456	74.56%
OATP2B1 inhibitior	-	0.5620	56.20%
OATP1B1 inhibitior	+	0.8001	80.01%
OATP1B3 inhibitior	+	0.8306	83.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9314	93.14%
P-glycoprotein inhibitior	+	0.7494	74.94%
P-glycoprotein substrate	-	0.5080	50.80%
CYP3A4 substrate	+	0.7231	72.31%
CYP2C9 substrate	-	0.8108	81.08%
CYP2D6 substrate	-	0.8629	86.29%
CYP3A4 inhibition	-	0.7174	71.74%
CYP2C9 inhibition	-	0.7835	78.35%
CYP2C19 inhibition	-	0.7964	79.64%
CYP2D6 inhibition	-	0.9440	94.40%
CYP1A2 inhibition	-	0.8929	89.29%
CYP2C8 inhibition	+	0.7093	70.93%
CYP inhibitory promiscuity	-	0.6926	69.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6248	62.48%
Eye corrosion	-	0.9954	99.54%
Eye irritation	-	0.8929	89.29%
Skin irritation	+	0.6634	66.34%
Skin corrosion	-	0.9570	95.70%
Ames mutagenesis	-	0.8137	81.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3684	36.84%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6901	69.01%
skin sensitisation	-	0.7196	71.96%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8036	80.36%
Acute Oral Toxicity (c)	I	0.6405	64.05%
Estrogen receptor binding	+	0.7098	70.98%
Androgen receptor binding	+	0.7084	70.84%
Thyroid receptor binding	-	0.5388	53.88%
Glucocorticoid receptor binding	+	0.6074	60.74%
Aromatase binding	+	0.6371	63.71%
PPAR gamma	+	0.6606	66.06%
Honey bee toxicity	-	0.6951	69.51%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.8318	83.18%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL230	P35354	Cyclooxygenase-2	370 nM	IC50	PMID: 16562850

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.04%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.24%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	96.31%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.26%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	95.25%	96.95%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	94.73%	92.86%
CHEMBL2581	P07339	Cathepsin D	94.71%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.61%	99.17%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	93.73%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.45%	94.45%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	93.30%	85.94%
CHEMBL4227	P25090	Lipoxin A4 receptor	92.84%	100.00%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	92.30%	97.29%
CHEMBL299	P17252	Protein kinase C alpha	91.66%	98.03%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	90.99%	92.08%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.69%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.26%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	88.19%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.85%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.86%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.13%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.09%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.00%	93.56%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	84.61%	82.50%
CHEMBL340	P08684	Cytochrome P450 3A4	83.76%	91.19%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	83.55%	94.01%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.49%	82.69%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.07%	91.24%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.49%	96.90%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.48%	92.94%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	82.35%	96.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.78%	94.33%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.59%	97.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.57%	97.21%

Plants that contains it

• Aegiceras corniculatum
• Ajuga integrifolia
• Allium multibulbosum
• Arbutus menziesii
• Bruguiera gymnorhiza
• Cinnamosma madagascariensis
• Echiochilon pauciflorum
• Helichrysum nudifolium
• Hypoxis nyasica
• Isoberlinia angolensis
• Macaranga sinensis
• Mirabilis jalapa
• Nicoteba betonica
• Otostegia fruticosa
• Paranephelius uniflorus
• Rhododendron aureum
• Seriphidium lessingianum
• Sonneratia alba
• Tephroseris integrifolia
• Terminalia tetraphylla
• Teucrium orientale
• Veltheimia capensis
• Xylopia aethiopica

Cross-Links

• PubChem: 11513260
• NPASS: NPC119036
• ChEMBL: CHEMBL504631
• LOTUS: LTS0137634
• wikiData: Q104923607