Sarsalignenone

Details

• Internal ID: 074715e7-4aaa-43b6-ae2a-ba36a85dcc51
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Oxosteroids
• IUPAC Name: (E)-N-[(3S,8R,9S,10R,13R,17S)-17-[(1S)-1-(dimethylamino)ethyl]-10,13-dimethyl-4-oxo-1,2,3,7,8,9,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-yl]-2-methylbut-2-enamide
• SMILES (Canonical): CC=C(C)C(=O)NC1CCC2(C3CCC4(C(CC=C4C3CC=C2C1=O)C(C)N(C)C)C)C
• SMILES (Isomeric): C/C=C(\C)/C(=O)N[C@H]1CC[C@@]2([C@H]3CC[C@@]4([C@H](CC=C4[C@@H]3CC=C2C1=O)[C@H](C)N(C)C)C)C
• InChI: InChI=1S/C28H42N2O2/c1-8-17(2)26(32)29-24-14-16-28(5)22-13-15-27(4)20(18(3)30(6)7)11-12-21(27)19(22)9-10-23(28)25(24)31/h8,10,12,18-20,22,24H,9,11,13-16H2,1-7H3,(H,29,32)/b17-8+/t18-,19-,20+,22-,24-,27+,28+/m0/s1
• InChI Key: GCHGDPVSONOHQE-PNUJEHDGSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₂N₂O₂
• Molecular Weight: 438.60 g/mol
• Exact Mass: 438.324628587 g/mol
• Topological Polar Surface Area (TPSA): 49.40 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.07
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• BDBM50135146
• (E)-2-Methyl-but-2-enoic acid [(3S,8R,9S,10R,13R,17S)-17-((S)-1-dimethylamino-ethyl)-10,13-dimethyl-4-oxo-2,3,4,7,8,9,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]-amide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9950	99.50%
Caco-2	-	0.6503	65.03%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5973	59.73%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8933	89.33%
OATP1B3 inhibitior	+	0.9416	94.16%
MATE1 inhibitior	-	0.7081	70.81%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.9609	96.09%
P-glycoprotein inhibitior	+	0.7643	76.43%
P-glycoprotein substrate	-	0.5079	50.79%
CYP3A4 substrate	+	0.6778	67.78%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8069	80.69%
CYP3A4 inhibition	-	0.7704	77.04%
CYP2C9 inhibition	-	0.6010	60.10%
CYP2C19 inhibition	-	0.6504	65.04%
CYP2D6 inhibition	-	0.8512	85.12%
CYP1A2 inhibition	-	0.7811	78.11%
CYP2C8 inhibition	-	0.6662	66.62%
CYP inhibitory promiscuity	-	0.5948	59.48%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5467	54.67%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.9741	97.41%
Skin irritation	-	0.7245	72.45%
Skin corrosion	-	0.8699	86.99%
Ames mutagenesis	-	0.5544	55.44%
Human Ether-a-go-go-Related Gene inhibition	+	0.7885	78.85%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.6134	61.34%
skin sensitisation	-	0.8180	81.80%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.6955	69.55%
Acute Oral Toxicity (c)	III	0.5236	52.36%
Estrogen receptor binding	+	0.7725	77.25%
Androgen receptor binding	+	0.7396	73.96%
Thyroid receptor binding	+	0.6626	66.26%
Glucocorticoid receptor binding	+	0.7589	75.89%
Aromatase binding	+	0.6691	66.91%
PPAR gamma	+	0.5503	55.03%
Honey bee toxicity	-	0.8377	83.77%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9660	96.60%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	5754.4 nM	IC50	PMID: 21894898
CHEMBL1914	P06276	Butyrylcholinesterase	4290 nM	IC50	PMID: 23013356

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.06%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.66%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.94%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.89%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	89.18%	95.93%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.29%	93.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.94%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	86.78%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.51%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.17%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.09%	90.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.59%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.51%	100.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.29%	91.03%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.47%	89.34%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.42%	96.77%
CHEMBL284	P27487	Dipeptidyl peptidase IV	84.28%	95.69%
CHEMBL1871	P10275	Androgen Receptor	84.06%	96.43%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.92%	93.03%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.55%	85.30%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.36%	85.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.16%	95.89%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	81.95%	88.81%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.61%	89.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	81.27%	80.96%
CHEMBL5028	O14672	ADAM10	80.55%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.48%	94.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.10%	93.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.04%	99.23%

Plants that contains it

• Sarcococca saligna

Cross-Links

• PubChem: 44358110
• NPASS: NPC226509
• ChEMBL: CHEMBL137039
• LOTUS: LTS0069761
• wikiData: Q104667646