Esculeogenin B

Details

• Internal ID: 49aeb36a-e0d4-4490-9a9c-d7a691612272
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Solanocapsine-type alkaloids
• IUPAC Name: (1S,2R,5S,7S,10S,11S,14S,15R,16S,17S,20S,22R,24S)-20-(hydroxymethyl)-10,14,16-trimethyl-23-oxa-18-azahexacyclo[12.11.0.02,11.05,10.015,24.017,22]pentacosane-7,22-diol
• SMILES (Canonical): CC1C2C(CC3C2(CCC4C3CCC5C4(CCC(C5)O)C)C)OC6(C1NCC(C6)CO)O
• SMILES (Isomeric): C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC[C@@H]5[C@@]4(CC[C@@H](C5)O)C)C)O[C@]6([C@H]1NC[C@H](C6)CO)O
• InChI: InChI=1S/C27H45NO4/c1-15-23-22(32-27(31)12-16(14-29)13-28-24(15)27)11-21-19-5-4-17-10-18(30)6-8-25(17,2)20(19)7-9-26(21,23)3/h15-24,28-31H,4-14H2,1-3H3/t15-,16-,17-,18-,19+,20-,21-,22-,23-,24-,25-,26-,27+/m0/s1
• InChI Key: AGNQTDBSAUJBFO-JCEQVCBNSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₅NO₄
• Molecular Weight: 447.60 g/mol
• Exact Mass: 447.33485892 g/mol
• Topological Polar Surface Area (TPSA): 82.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.31
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• (5alpha,22s,23r,25s)-22,26-epimino-16beta,23-epoxy-3beta,23,27-trihydroxycholestane
• (1S,2R,5S,7S,10S,11S,14S,15R,16S,17S,20S,22R,24S)-20-(Hydroxymethyl)-10,14,16-trimethyl-23-oxa-18-azahexacyclo[12.11.0.02,11.05,10.015,24.017,22]pentacosane-7,22-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5347	53.47%
Caco-2	-	0.6789	67.89%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Lysosomes	0.6769	67.69%
OATP2B1 inhibitior	-	0.5650	56.50%
OATP1B1 inhibitior	+	0.8561	85.61%
OATP1B3 inhibitior	+	0.9298	92.98%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.5392	53.92%
P-glycoprotein inhibitior	-	0.6703	67.03%
P-glycoprotein substrate	+	0.5595	55.95%
CYP3A4 substrate	+	0.7357	73.57%
CYP2C9 substrate	-	0.8096	80.96%
CYP2D6 substrate	-	0.6902	69.02%
CYP3A4 inhibition	-	0.9827	98.27%
CYP2C9 inhibition	-	0.9398	93.98%
CYP2C19 inhibition	-	0.8871	88.71%
CYP2D6 inhibition	-	0.9201	92.01%
CYP1A2 inhibition	-	0.9499	94.99%
CYP2C8 inhibition	+	0.4935	49.35%
CYP inhibitory promiscuity	-	0.9625	96.25%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6458	64.58%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.9529	95.29%
Skin irritation	-	0.7418	74.18%
Skin corrosion	-	0.9232	92.32%
Ames mutagenesis	-	0.7032	70.32%
Human Ether-a-go-go-Related Gene inhibition	-	0.4597	45.97%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.5589	55.89%
skin sensitisation	-	0.8494	84.94%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.5872	58.72%
Acute Oral Toxicity (c)	III	0.6249	62.49%
Estrogen receptor binding	+	0.6190	61.90%
Androgen receptor binding	+	0.5886	58.86%
Thyroid receptor binding	+	0.6555	65.55%
Glucocorticoid receptor binding	+	0.7494	74.94%
Aromatase binding	+	0.7021	70.21%
PPAR gamma	+	0.5424	54.24%
Honey bee toxicity	-	0.6651	66.51%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	-	0.7070	70.70%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL204	P00734	Thrombin	97.72%	96.01%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.47%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.12%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.49%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.37%	96.61%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	94.13%	89.05%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.01%	91.11%
CHEMBL3045	P05771	Protein kinase C beta	93.97%	97.63%
CHEMBL237	P41145	Kappa opioid receptor	93.83%	98.10%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	92.37%	96.95%
CHEMBL299	P17252	Protein kinase C alpha	92.19%	98.03%
CHEMBL2996	Q05655	Protein kinase C delta	91.90%	97.79%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.86%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.38%	94.45%
CHEMBL1871	P10275	Androgen Receptor	90.57%	96.43%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	88.70%	92.88%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.19%	95.50%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	86.86%	92.86%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.53%	91.03%
CHEMBL2431	P31751	Serine/threonine-protein kinase AKT2	84.29%	98.33%
CHEMBL4581	P52732	Kinesin-like protein 1	84.19%	93.18%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.91%	96.77%
CHEMBL221	P23219	Cyclooxygenase-1	83.75%	90.17%
CHEMBL233	P35372	Mu opioid receptor	83.25%	97.93%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.89%	92.94%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	82.59%	96.03%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.47%	96.21%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	82.25%	95.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.02%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.99%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.30%	86.33%

Plants that contains it

• Solanum lycopersicum

Cross-Links

• PubChem: 11430786
• NPASS: NPC33428