bruguierins B

Details

• Internal ID: fc7c5653-0707-4259-9eaa-7f0ce57dfb27
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(3S,5R,8R,9R,10S,11R,13R,14R,17S)-11-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)OC1CCC2(C(C1(C)C)CCC3(C2C(CC4C3(CCC4C(C)(CCC=C(C)C)O)C)O)C)C
• SMILES (Isomeric): CCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]3([C@@H]2[C@@H](C[C@H]4[C@]3(CC[C@@H]4[C@](C)(CCC=C(C)C)O)C)O)C)C
• InChI: InChI=1S/C48H86O4/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-27-42(50)52-41-30-32-45(6)40(44(41,4)5)29-34-47(8)43(45)39(49)35-38-37(28-33-46(38,47)7)48(9,51)31-25-26-36(2)3/h26,37-41,43,49,51H,10-25,27-35H2,1-9H3/t37-,38+,39+,40-,41-,43+,45-,46+,47+,48-/m0/s1
• InChI Key: BKABTFBEUWNOKF-MVGNDMLNSA-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: 16.20
• Atomic LogP (AlogP): 13.31
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 21

Synonyms

• CHEMBL447269
• InChI=1/C48H86O4/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-27-42(50)52-41-30-32-45(6)40(44(41,4)5)29-34-47(8)43(45)39(49)35-38-37(28-33-46(38,47)7)48(9,51)31-25-26-36(2)3/h26,37-41,43,49,51H,10-25,27-35H2,1-9H3/t37-,38+,39?,40-,41?,43+,45-,46+,47+,

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9968	99.68%
Caco-2	-	0.8287	82.87%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7878	78.78%
OATP2B1 inhibitior	-	0.5633	56.33%
OATP1B1 inhibitior	+	0.7113	71.13%
OATP1B3 inhibitior	+	0.8473	84.73%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9430	94.30%
P-glycoprotein inhibitior	+	0.7498	74.98%
P-glycoprotein substrate	-	0.5511	55.11%
CYP3A4 substrate	+	0.7388	73.88%
CYP2C9 substrate	-	0.8108	81.08%
CYP2D6 substrate	-	0.8629	86.29%
CYP3A4 inhibition	-	0.6578	65.78%
CYP2C9 inhibition	-	0.8508	85.08%
CYP2C19 inhibition	-	0.8797	87.97%
CYP2D6 inhibition	-	0.9301	93.01%
CYP1A2 inhibition	-	0.9330	93.30%
CYP2C8 inhibition	+	0.6680	66.80%
CYP inhibitory promiscuity	-	0.6374	63.74%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6769	67.69%
Eye corrosion	-	0.9960	99.60%
Eye irritation	-	0.8975	89.75%
Skin irritation	+	0.6580	65.80%
Skin corrosion	-	0.9649	96.49%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6431	64.31%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6440	64.40%
skin sensitisation	-	0.6550	65.50%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8309	83.09%
Acute Oral Toxicity (c)	III	0.4403	44.03%
Estrogen receptor binding	+	0.7173	71.73%
Androgen receptor binding	+	0.7077	70.77%
Thyroid receptor binding	-	0.5558	55.58%
Glucocorticoid receptor binding	+	0.5774	57.74%
Aromatase binding	+	0.6228	62.28%
PPAR gamma	+	0.6478	64.78%
Honey bee toxicity	-	0.7317	73.17%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.8418	84.18%
Fish aquatic toxicity	+	1.0000	100.00%

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	99.38%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.74%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.19%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	96.96%	97.79%
CHEMBL299	P17252	Protein kinase C alpha	95.53%	98.03%
CHEMBL2581	P07339	Cathepsin D	94.04%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.03%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.40%	99.17%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	92.97%	100.00%
CHEMBL1914	P06276	Butyrylcholinesterase	92.67%	95.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	92.44%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.35%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.27%	97.09%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	90.68%	85.94%
CHEMBL5255	O00206	Toll-like receptor 4	89.92%	92.50%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	89.01%	92.86%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	88.91%	82.50%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	88.69%	92.08%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.63%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.51%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.72%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.66%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	85.06%	91.19%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	85.02%	97.29%
CHEMBL1902	P62942	FK506-binding protein 1A	84.98%	97.05%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.96%	92.62%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.32%	93.56%
CHEMBL1871	P10275	Androgen Receptor	83.23%	96.43%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.14%	96.90%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.83%	85.31%
CHEMBL5028	O14672	ADAM10	82.73%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.68%	94.33%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.67%	97.50%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	80.86%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	80.85%	90.17%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	80.09%	96.25%

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: 11657758
• NPASS: NPC279974
• ChEMBL: CHEMBL447269
• LOTUS: LTS0271362
• wikiData: Q104937465