Broussonetine I

Details

• Internal ID: d7bb187b-cc04-4801-840c-01c9af241704
• Taxonomy: Organoheterocyclic compounds > Piperidines > N-acylpiperidines
• IUPAC Name: 1-[(2R)-2-[(1S,2S)-8-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1,2-dihydroxyoctyl]piperidin-1-yl]ethanone
• SMILES (Canonical): CC(=O)N1CCCCC1C(C(CCCCCCC2C(C(C(N2)CO)O)O)O)O
• SMILES (Isomeric): CC(=O)N1CCCC[C@@H]1[C@@H]([C@H](CCCCCC[C@@H]2[C@H]([C@@H]([C@H](N2)CO)O)O)O)O
• InChI: InChI=1S/C20H38N2O6/c1-13(24)22-11-7-6-9-16(22)20(28)17(25)10-5-3-2-4-8-14-18(26)19(27)15(12-23)21-14/h14-21,23,25-28H,2-12H2,1H3/t14-,15-,16-,17+,18-,19-,20+/m1/s1
• InChI Key: JOZUWNJNFDODBK-KDQPAEPOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₈N₂O₆
• Molecular Weight: 402.50 g/mol
• Exact Mass: 402.27298694 g/mol
• Topological Polar Surface Area (TPSA): 134.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.50
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

• 1-((2R)-2-((1S,2S)-8-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)-1,2-dihydroxyoctyl)piperidin-1-yl)ethanone
• 1-[(2R)-2-[(1S,2S)-8-[(2R,3R,4R,5R)-3,4-Dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1,2-dihydroxyoctyl]piperidin-1-yl]ethanone
• RefChem:917624
• 215117-10-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6520	65.20%
Caco-2	-	0.8078	80.78%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6282	62.82%
OATP2B1 inhibitior	-	0.7157	71.57%
OATP1B1 inhibitior	+	0.9372	93.72%
OATP1B3 inhibitior	+	0.9378	93.78%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5383	53.83%
P-glycoprotein inhibitior	-	0.8197	81.97%
P-glycoprotein substrate	+	0.6430	64.30%
CYP3A4 substrate	+	0.6244	62.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7414	74.14%
CYP3A4 inhibition	-	0.9948	99.48%
CYP2C9 inhibition	-	0.9400	94.00%
CYP2C19 inhibition	-	0.9615	96.15%
CYP2D6 inhibition	-	0.9375	93.75%
CYP1A2 inhibition	-	0.9638	96.38%
CYP2C8 inhibition	-	0.9141	91.41%
CYP inhibitory promiscuity	-	0.9791	97.91%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6661	66.61%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9381	93.81%
Skin irritation	-	0.7663	76.63%
Skin corrosion	-	0.9242	92.42%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7967	79.67%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	-	0.5728	57.28%
skin sensitisation	-	0.9021	90.21%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.5343	53.43%
Acute Oral Toxicity (c)	III	0.5833	58.33%
Estrogen receptor binding	-	0.5385	53.85%
Androgen receptor binding	-	0.5441	54.41%
Thyroid receptor binding	-	0.5362	53.62%
Glucocorticoid receptor binding	-	0.5355	53.55%
Aromatase binding	-	0.6471	64.71%
PPAR gamma	-	0.6779	67.79%
Honey bee toxicity	-	0.9259	92.59%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.7107	71.07%
Fish aquatic toxicity	-	0.9248	92.48%

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	99.40%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.42%	98.95%
CHEMBL237	P41145	Kappa opioid receptor	96.21%	98.10%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.84%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.62%	97.09%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	93.60%	98.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	93.48%	90.08%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	92.30%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.35%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.05%	93.56%
CHEMBL340	P08684	Cytochrome P450 3A4	89.94%	91.19%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.83%	96.47%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.82%	96.77%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	88.37%	97.47%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.37%	100.00%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	88.15%	91.81%
CHEMBL5255	O00206	Toll-like receptor 4	87.31%	92.50%
CHEMBL3524	P56524	Histone deacetylase 4	86.74%	92.97%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.61%	93.04%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	86.41%	98.75%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.28%	100.00%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	85.60%	95.58%
CHEMBL5203	P33316	dUTP pyrophosphatase	85.40%	99.18%
CHEMBL274	P51681	C-C chemokine receptor type 5	84.47%	98.77%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.34%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.77%	95.89%
CHEMBL4683	Q12884	Fibroblast activation protein alpha	83.56%	93.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.39%	100.00%
CHEMBL1873	P00750	Tissue-type plasminogen activator	83.28%	93.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.12%	94.33%
CHEMBL2514	O95665	Neurotensin receptor 2	82.61%	100.00%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	80.74%	95.36%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	80.45%	96.03%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.33%	93.03%
CHEMBL3024	P53350	Serine/threonine-protein kinase PLK1	80.29%	97.43%

Plants that contains it

• Broussonetia kazinoki
• Broussonetia papyrifera

Cross-Links

• PubChem: 10644810
• LOTUS: LTS0181015
• wikiData: Q105132606