(E)-N-[(3S,5S,8R,9S,10S,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-N,3,4-trimethylpent-2-enamide

Details

• Internal ID: be27a170-e642-4164-8aa2-42a24299edbc
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Azasteroids and derivatives
• IUPAC Name: (E)-N-[(3S,5S,8R,9S,10S,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-N,3,4-trimethylpent-2-enamide
• SMILES (Canonical): CC(C)C(=CC(=O)N(C)C1CCC2(C(C1)CCC3C2CCC4(C3CCC4C(C)N(C)C)C)C)C
• 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](C4)N(C)C(=O)/C=C(\C)/C(C)C)C)C)N(C)C
• InChI: InChI=1S/C31H54N2O/c1-20(2)21(3)18-29(34)33(9)24-14-16-30(5)23(19-24)10-11-25-27-13-12-26(22(4)32(7)8)31(27,6)17-15-28(25)30/h18,20,22-28H,10-17,19H2,1-9H3/b21-18+/t22-,23-,24-,25-,26+,27-,28-,30-,31+/m0/s1
• InChI Key: WCBPBBFIAODRLI-AWUJJIRRSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₅₄N₂O
• Molecular Weight: 470.80 g/mol
• Exact Mass: 470.423614350 g/mol
• Topological Polar Surface Area (TPSA): 23.60 Ų
• XlogP: 8.30
• Atomic LogP (AlogP): 7.02
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• Salignenamide F
• BDBM50135153
• (E)-3,4-Dimethyl-pent-2-enoic acid [(3S,5S,8R,9S,10S,13S,14S,17S)-17-((S)-1-dimethylamino-ethyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl]-methyl-amide
• 3,4-Dimethyl-pent-2-enoic acid [(3S,5S,8R,9S,10S,13S,14S,17S)-17-(1-dimethylamino-ethyl)-10-methyl-13-(S)-methyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl]-methyl-amide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9855	98.55%
Caco-2	-	0.6222	62.22%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Plasma membrane	0.3478	34.78%
OATP2B1 inhibitior	-	0.7194	71.94%
OATP1B1 inhibitior	+	0.8312	83.12%
OATP1B3 inhibitior	+	0.9339	93.39%
MATE1 inhibitior	-	0.7027	70.27%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.8546	85.46%
P-glycoprotein inhibitior	+	0.6690	66.90%
P-glycoprotein substrate	-	0.5656	56.56%
CYP3A4 substrate	+	0.7354	73.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8086	80.86%
CYP3A4 inhibition	-	0.6791	67.91%
CYP2C9 inhibition	-	0.5645	56.45%
CYP2C19 inhibition	-	0.6483	64.83%
CYP2D6 inhibition	-	0.8993	89.93%
CYP1A2 inhibition	-	0.7196	71.96%
CYP2C8 inhibition	-	0.7633	76.33%
CYP inhibitory promiscuity	+	0.5654	56.54%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.5850	58.50%
Eye corrosion	-	0.9689	96.89%
Eye irritation	-	0.9503	95.03%
Skin irritation	-	0.6586	65.86%
Skin corrosion	-	0.7481	74.81%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3670	36.70%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.5558	55.58%
skin sensitisation	-	0.7708	77.08%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8450	84.50%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.8090	80.90%
Androgen receptor binding	+	0.7943	79.43%
Thyroid receptor binding	+	0.5645	56.45%
Glucocorticoid receptor binding	+	0.6509	65.09%
Aromatase binding	+	0.5983	59.83%
PPAR gamma	+	0.6706	67.06%
Honey bee toxicity	-	0.6859	68.59%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9846	98.46%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	6456.54 nM	IC50	PMID: 14643329
CHEMBL1914	P06276	Butyrylcholinesterase	4070 nM	IC50	PMID: 14584959

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.78%	96.09%
CHEMBL204	P00734	Thrombin	93.91%	96.01%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.66%	97.25%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	92.28%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.83%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.49%	100.00%
CHEMBL237	P41145	Kappa opioid receptor	91.35%	98.10%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.47%	96.77%
CHEMBL340	P08684	Cytochrome P450 3A4	89.15%	91.19%
CHEMBL1871	P10275	Androgen Receptor	88.29%	96.43%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.29%	95.89%
CHEMBL3837	P07711	Cathepsin L	87.77%	96.61%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	85.45%	97.47%
CHEMBL4370	P16662	UDP-glucuronosyltransferase 2B7	84.73%	100.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	84.56%	97.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.53%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.12%	90.71%
CHEMBL2179	P04062	Beta-glucocerebrosidase	83.80%	85.31%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.74%	91.03%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	83.51%	85.30%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.84%	96.47%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.79%	94.33%
CHEMBL236	P41143	Delta opioid receptor	82.39%	99.35%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	81.85%	80.96%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.40%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.36%	95.56%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.26%	95.71%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.17%	93.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.35%	92.62%
CHEMBL2514	O95665	Neurotensin receptor 2	80.17%	100.00%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.06%	85.11%

Plants that contains it

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

Cross-Links

• PubChem: 11113449
• NPASS: NPC147513
• ChEMBL: CHEMBL344593
• LOTUS: LTS0168741
• wikiData: Q104667141