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

Details

• Internal ID: 5f9f29d7-d7ea-4a0c-83c7-b58af550f598
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Hydroxysteroids
• IUPAC Name: (E)-N-[(3S,4R,8S,9S,10R,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-4-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]-2-methylbut-2-enamide
• SMILES (Canonical): CC=C(C)C(=O)NC1CCC2(C3CCC4(C(C3CC=C2C1O)CCC4C(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]([C@@H]3CC=C2[C@H]1O)CC[C@@H]4[C@H](C)N(C)C)C)C
• InChI: InChI=1S/C28H46N2O2/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/h8,10,18-22,24-25,31H,9,11-16H2,1-7H3,(H,29,32)/b17-8+/t18-,19-,20+,21-,22-,24-,25+,27+,28+/m0/s1
• InChI Key: VLFYYOVMWNJQBE-KFRXLHHWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₆N₂O₂
• Molecular Weight: 442.70 g/mol
• Exact Mass: 442.35592871 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.94
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• BDBM50421635

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9866	98.66%
Caco-2	-	0.6488	64.88%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6525	65.25%
OATP2B1 inhibitior	-	0.7171	71.71%
OATP1B1 inhibitior	+	0.8896	88.96%
OATP1B3 inhibitior	+	0.9406	94.06%
MATE1 inhibitior	-	0.8726	87.26%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8915	89.15%
P-glycoprotein inhibitior	-	0.4382	43.82%
P-glycoprotein substrate	+	0.5113	51.13%
CYP3A4 substrate	+	0.7419	74.19%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.7916	79.16%
CYP3A4 inhibition	-	0.6174	61.74%
CYP2C9 inhibition	-	0.5869	58.69%
CYP2C19 inhibition	-	0.6698	66.98%
CYP2D6 inhibition	-	0.7834	78.34%
CYP1A2 inhibition	-	0.8094	80.94%
CYP2C8 inhibition	-	0.6667	66.67%
CYP inhibitory promiscuity	-	0.6210	62.10%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5722	57.22%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.9776	97.76%
Skin irritation	-	0.7265	72.65%
Skin corrosion	-	0.8864	88.64%
Ames mutagenesis	-	0.5944	59.44%
Human Ether-a-go-go-Related Gene inhibition	+	0.7926	79.26%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.6660	66.60%
skin sensitisation	-	0.8303	83.03%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8650	86.50%
Acute Oral Toxicity (c)	III	0.5172	51.72%
Estrogen receptor binding	+	0.8312	83.12%
Androgen receptor binding	+	0.7781	77.81%
Thyroid receptor binding	+	0.6714	67.14%
Glucocorticoid receptor binding	+	0.7256	72.56%
Aromatase binding	+	0.6744	67.44%
PPAR gamma	+	0.5741	57.41%
Honey bee toxicity	-	0.7838	78.38%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9690	96.90%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	30199.52 nM	IC50	PMID: 19606850

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.79%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	95.48%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.84%	91.11%
CHEMBL1871	P10275	Androgen Receptor	92.76%	96.43%
CHEMBL2581	P07339	Cathepsin D	92.70%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.00%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.03%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	87.90%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.84%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.82%	93.00%
CHEMBL226	P30542	Adenosine A1 receptor	86.46%	95.93%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.73%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.10%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.04%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.52%	97.25%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.69%	93.56%
CHEMBL5028	O14672	ADAM10	83.20%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.33%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.20%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.78%	95.56%

Plants that contains it

• Garcinia cowa
• Garcinia oblongifolia
• Sarcococca saligna
• Symphonia globulifera

Cross-Links

• PubChem: 11154961
• NPASS: NPC471083
• ChEMBL: CHEMBL2368067
• LOTUS: LTS0011355
• wikiData: Q105191515