Isoesculeogenin A

Details

• Internal ID: 45982089-d71e-4f30-9378-0979e0812b19
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Spirosolanes and derivatives
• IUPAC Name: (1R,2S,3'R,4S,5'S,6R,7S,8R,9S,12S,13S,16S,18S)-5'-(hydroxymethyl)-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-3',16-diol
• SMILES (Canonical): CC1C2C(CC3C2(CCC4C3CCC5C4(CCC(C5)O)C)C)OC16C(CC(CN6)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@@]16[C@@H](C[C@@H](CN6)CO)O
• InChI: InChI=1S/C27H45NO4/c1-15-24-22(32-27(15)23(31)10-16(14-29)13-28-27)12-21-19-5-4-17-11-18(30)6-8-25(17,2)20(19)7-9-26(21,24)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: FBKQAVWTYDQPAB-WSORYGKISA-N
• Popularity: 4 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

• (1R,2S,3'R,4S,5'S,6R,7S,8R,9S,12S,13S,16S,18S)-5'-(Hydroxymethyl)-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-3',16-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6716	67.16%
Caco-2	-	0.7341	73.41%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.5058	50.58%
OATP2B1 inhibitior	-	0.5629	56.29%
OATP1B1 inhibitior	+	0.8679	86.79%
OATP1B3 inhibitior	+	0.9463	94.63%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.7691	76.91%
P-glycoprotein inhibitior	-	0.6916	69.16%
P-glycoprotein substrate	+	0.5753	57.53%
CYP3A4 substrate	+	0.7161	71.61%
CYP2C9 substrate	-	0.8100	81.00%
CYP2D6 substrate	-	0.7181	71.81%
CYP3A4 inhibition	-	0.9781	97.81%
CYP2C9 inhibition	-	0.9171	91.71%
CYP2C19 inhibition	-	0.8919	89.19%
CYP2D6 inhibition	-	0.9223	92.23%
CYP1A2 inhibition	-	0.9458	94.58%
CYP2C8 inhibition	+	0.4799	47.99%
CYP inhibitory promiscuity	-	0.9221	92.21%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6213	62.13%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9566	95.66%
Skin irritation	-	0.7559	75.59%
Skin corrosion	-	0.9185	91.85%
Ames mutagenesis	-	0.6656	66.56%
Human Ether-a-go-go-Related Gene inhibition	-	0.3864	38.64%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.6535	65.35%
skin sensitisation	-	0.8432	84.32%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.7052	70.52%
Acute Oral Toxicity (c)	III	0.6447	64.47%
Estrogen receptor binding	+	0.5873	58.73%
Androgen receptor binding	-	0.5696	56.96%
Thyroid receptor binding	+	0.7174	71.74%
Glucocorticoid receptor binding	+	0.7745	77.45%
Aromatase binding	+	0.7205	72.05%
PPAR gamma	+	0.5841	58.41%
Honey bee toxicity	-	0.7110	71.10%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.8169	81.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL204	P00734	Thrombin	97.89%	96.01%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.64%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.50%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.07%	96.61%
CHEMBL237	P41145	Kappa opioid receptor	95.23%	98.10%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.00%	97.25%
CHEMBL3045	P05771	Protein kinase C beta	92.54%	97.63%
CHEMBL233	P35372	Mu opioid receptor	92.21%	97.93%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	91.54%	89.05%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.43%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.34%	100.00%
CHEMBL2996	Q05655	Protein kinase C delta	90.13%	97.79%
CHEMBL1871	P10275	Androgen Receptor	88.73%	96.43%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.99%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.46%	94.45%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	84.66%	95.58%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.37%	95.50%
CHEMBL4581	P52732	Kinesin-like protein 1	84.31%	93.18%
CHEMBL299	P17252	Protein kinase C alpha	83.80%	98.03%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.75%	96.77%
CHEMBL221	P23219	Cyclooxygenase-1	83.23%	90.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.00%	96.21%
CHEMBL226	P30542	Adenosine A1 receptor	81.50%	95.93%
CHEMBL4482	O96013	Serine/threonine-protein kinase PAK 4	81.41%	95.42%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.34%	92.94%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.31%	93.04%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.69%	92.86%
CHEMBL228	P31645	Serotonin transporter	80.36%	95.51%
CHEMBL2431	P31751	Serine/threonine-protein kinase AKT2	80.08%	98.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.06%	95.89%

Plants that contains it

• Solanum lycopersicum

Cross-Links

• PubChem: 11351338
• NPASS: NPC25947