bruguierins C

Details

• Internal ID: 3a54b89d-962f-433d-8529-7265859c9023
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(1R,3S,5S,8R,9S,10R,13R,14R,17S)-17-[(E,2S)-6-hydroperoxy-2-hydroxy-6-methylhept-4-en-2-yl]-1-hydroxy-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)(CC=CC(C)(C)OO)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)(C/C=C/C(C)(C)OO)O)C)O
• InChI: InChI=1S/C48H86O6/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-26-42(50)53-41-35-40(49)48(9)38(44(41,4)5)30-34-46(7)39(48)28-27-36-37(29-33-45(36,46)6)47(8,51)32-25-31-43(2,3)54-52/h25,31,36-41,49,51-52H,10-24,26-30,32-35H2,1-9H3/b31-25+/t36-,37+,38+,39+,40-,41+,45-,46-,47+,48+/m1/s1
• InChI Key: PNIOLRUIMUJAKL-MZOLOXAHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₈₆O₆
• Molecular Weight: 759.20 g/mol
• Exact Mass: 758.64244046 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 15.00
• Atomic LogP (AlogP): 12.78
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 22

Synonyms

• CHEMBL503931
• InChI=1/C48H86O6/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-26-42(50)53-41-35-40(49)48(9)38(44(41,4)5)30-34-46(7)39(48)28-27-36-37(29-33-45(36,46)6)47(8,51)32-25-31-43(2,3)54-52/h25,31,36-41,49,51-52H,10-24,26-30,32-35H2,1-9H3/b31-25+/t36-,37+,38+,3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9923	99.23%
Caco-2	-	0.8391	83.91%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6317	63.17%
OATP2B1 inhibitior	-	0.5704	57.04%
OATP1B1 inhibitior	+	0.7878	78.78%
OATP1B3 inhibitior	+	0.8817	88.17%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9514	95.14%
P-glycoprotein inhibitior	+	0.7510	75.10%
P-glycoprotein substrate	+	0.5527	55.27%
CYP3A4 substrate	+	0.7298	72.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8705	87.05%
CYP3A4 inhibition	-	0.7069	70.69%
CYP2C9 inhibition	-	0.8166	81.66%
CYP2C19 inhibition	-	0.7703	77.03%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.8477	84.77%
CYP2C8 inhibition	+	0.7388	73.88%
CYP inhibitory promiscuity	-	0.7864	78.64%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6501	65.01%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9022	90.22%
Skin irritation	+	0.5539	55.39%
Skin corrosion	-	0.8987	89.87%
Ames mutagenesis	-	0.6837	68.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6553	65.53%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.7645	76.45%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8504	85.04%
Acute Oral Toxicity (c)	I	0.4547	45.47%
Estrogen receptor binding	+	0.7525	75.25%
Androgen receptor binding	+	0.7077	70.77%
Thyroid receptor binding	-	0.5063	50.63%
Glucocorticoid receptor binding	+	0.6348	63.48%
Aromatase binding	+	0.6431	64.31%
PPAR gamma	+	0.6570	65.70%
Honey bee toxicity	-	0.7168	71.68%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.8093	80.93%
Fish aquatic toxicity	+	0.9973	99.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.44%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.74%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.59%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	96.02%	97.79%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	95.43%	92.86%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.33%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.85%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	94.09%	96.95%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	93.24%	100.00%
CHEMBL2581	P07339	Cathepsin D	93.17%	98.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	92.54%	100.00%
CHEMBL299	P17252	Protein kinase C alpha	91.94%	98.03%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	90.72%	97.29%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.24%	86.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.52%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.41%	97.09%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	87.93%	94.01%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.34%	95.89%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	86.98%	85.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.02%	95.56%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.61%	91.24%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.52%	92.62%
CHEMBL5255	O00206	Toll-like receptor 4	85.50%	92.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.65%	96.61%
CHEMBL340	P08684	Cytochrome P450 3A4	84.04%	91.19%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.25%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.09%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.14%	93.56%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.15%	82.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.98%	92.94%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	80.97%	96.25%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.23%	92.88%

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: 11629176
• NPASS: NPC222153
• ChEMBL: CHEMBL503931
• LOTUS: LTS0266753
• wikiData: Q105211958