(20S)-3beta-(3-Methyl-2-butenoylamino)-4beta-acetoxy-20-(methylamino)-5alpha-pregnane

Details

• Internal ID: d6801654-6ee6-4e27-85cd-72a0922b017e
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Oxosteroids > 16-oxosteroids
• IUPAC Name: [(3S,4R,5R,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-[(1S)-1-(methylamino)ethyl]-3-(3-methylbut-2-enoylamino)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-4-yl] acetate
• SMILES (Canonical): CC(C1CCC2C1(CCC3C2CCC4C3(CCC(C4OC(=O)C)NC(=O)C=C(C)C)C)C)NC
• SMILES (Isomeric): C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@@H]([C@@H]4OC(=O)C)NC(=O)C=C(C)C)C)C)NC
• InChI: InChI=1S/C29H48N2O3/c1-17(2)16-26(33)31-25-13-15-29(6)23-12-14-28(5)21(18(3)30-7)10-11-22(28)20(23)8-9-24(29)27(25)34-19(4)32/h16,18,20-25,27,30H,8-15H2,1-7H3,(H,31,33)/t18-,20-,21+,22-,23-,24-,25-,27+,28+,29+/m0/s1
• InChI Key: LQBHXRUVFBZZNM-AQEYLYCMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₈N₂O₃
• Molecular Weight: 472.70 g/mol
• Exact Mass: 472.36649340 g/mol
• Topological Polar Surface Area (TPSA): 67.40 Ų
• XlogP: 6.30
• Atomic LogP (AlogP): 5.25
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• (20S)-3beta-(3-Methyl-2-butenoylamino)-4beta-acetoxy-20-(methylamino)-5alpha-pregnane

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9902	99.02%
Caco-2	-	0.6857	68.57%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7136	71.36%
OATP2B1 inhibitior	-	0.7170	71.70%
OATP1B1 inhibitior	+	0.8307	83.07%
OATP1B3 inhibitior	+	0.9145	91.45%
MATE1 inhibitior	-	0.5672	56.72%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.9308	93.08%
P-glycoprotein inhibitior	+	0.7103	71.03%
P-glycoprotein substrate	-	0.6144	61.44%
CYP3A4 substrate	+	0.7253	72.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8534	85.34%
CYP3A4 inhibition	-	0.7879	78.79%
CYP2C9 inhibition	+	0.6960	69.60%
CYP2C19 inhibition	+	0.5699	56.99%
CYP2D6 inhibition	-	0.9004	90.04%
CYP1A2 inhibition	-	0.8482	84.82%
CYP2C8 inhibition	-	0.6803	68.03%
CYP inhibitory promiscuity	+	0.7691	76.91%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5714	57.14%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9633	96.33%
Skin irritation	-	0.7258	72.58%
Skin corrosion	-	0.9342	93.42%
Ames mutagenesis	-	0.6337	63.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.8140	81.40%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	+	0.5513	55.13%
skin sensitisation	-	0.8327	83.27%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6981	69.81%
Acute Oral Toxicity (c)	III	0.4703	47.03%
Estrogen receptor binding	+	0.7846	78.46%
Androgen receptor binding	+	0.6971	69.71%
Thyroid receptor binding	+	0.6451	64.51%
Glucocorticoid receptor binding	+	0.6477	64.77%
Aromatase binding	+	0.6858	68.58%
PPAR gamma	+	0.7005	70.05%
Honey bee toxicity	-	0.5062	50.62%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9946	99.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.34%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.26%	96.09%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	95.09%	95.58%
CHEMBL204	P00734	Thrombin	94.74%	96.01%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.59%	96.38%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.06%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.57%	91.11%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	89.33%	95.36%
CHEMBL340	P08684	Cytochrome P450 3A4	88.98%	91.19%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	88.66%	91.03%
CHEMBL2413	P32246	C-C chemokine receptor type 1	87.78%	89.50%
CHEMBL2581	P07339	Cathepsin D	87.34%	98.95%
CHEMBL3055	P50613	Cyclin-dependent kinase 7	87.29%	81.88%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.05%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.35%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.11%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.26%	94.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.71%	95.71%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.43%	96.61%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	84.29%	97.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.96%	95.89%
CHEMBL5028	O14672	ADAM10	82.93%	97.50%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	82.39%	89.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.39%	97.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.27%	82.69%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.08%	92.88%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.05%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.00%	97.28%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.79%	93.03%
CHEMBL237	P41145	Kappa opioid receptor	81.21%	98.10%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.04%	95.71%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.03%	85.30%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.90%	91.07%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.78%	82.50%
CHEMBL299	P17252	Protein kinase C alpha	80.64%	98.03%

Plants that contains it

• Alpinia galanga
• Ampelopsis japonica
• Cneorum pulverulentum
• Sarcococca hookeriana

Cross-Links

• PubChem: 44587282
• NPASS: NPC72753
• ChEMBL: CHEMBL504923
• LOTUS: LTS0024791
• wikiData: Q105155466