Acetic acid,4b,8-trimethyl-2(1H)-phenanthrenylidene]-, 2-(methylamino)ethyl ester, [1R-(1alpha,2E,4aalpha,4bbeta,7beta,8beta,8aalpha,10beta,10abeta)]-

Details

• Internal ID: 9c8883b8-cbd0-44c9-9f91-4184e3403b61
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Hydroxysteroids > 6-hydroxysteroids
• IUPAC Name: 2-(methylamino)ethyl (2E)-2-[(1R,4aS,4bR,7S,8R,8aR,10S,10aS)-7-acetyloxy-8-formyl-10-hydroxy-1,4b,8-trimethyl-3,4,4a,5,6,7,8a,9,10,10a-decahydro-1H-phenanthren-2-ylidene]acetate
• SMILES (Canonical): CC1C2C(CCC1=CC(=O)OCCNC)C3(CCC(C(C3CC2O)(C)C=O)OC(=O)C)C
• SMILES (Isomeric): C[C@@H]\1[C@H]2[C@H](CC/C1=C\C(=O)OCCNC)[C@]3(CC[C@@H]([C@]([C@@H]3C[C@@H]2O)(C)C=O)OC(=O)C)C
• InChI: InChI=1S/C25H39NO6/c1-15-17(12-22(30)31-11-10-26-5)6-7-18-23(15)19(29)13-20-24(18,3)9-8-21(32-16(2)28)25(20,4)14-27/h12,14-15,18-21,23,26,29H,6-11,13H2,1-5H3/b17-12+/t15-,18-,19-,20+,21-,23-,24+,25+/m0/s1
• InChI Key: QYQUUOBOLMCJEA-VVZAHHCISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₉NO₆
• Molecular Weight: 449.60 g/mol
• Exact Mass: 449.27773796 g/mol
• Topological Polar Surface Area (TPSA): 102.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.66
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• NSC-179181
• Acetic acid,4b,8-trimethyl-2(1H)-phenanthrenylidene]-, 2-(methylamino)ethyl ester, [1R-(1.alpha.,2E,4a.alpha.,4b.beta.,7.beta.,8.beta.,8a.alpha.,10.beta.,10a.beta.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9248	92.48%
Caco-2	-	0.6835	68.35%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7035	70.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8373	83.73%
OATP1B3 inhibitior	+	0.9151	91.51%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8770	87.70%
P-glycoprotein inhibitior	+	0.7192	71.92%
P-glycoprotein substrate	+	0.5333	53.33%
CYP3A4 substrate	+	0.7362	73.62%
CYP2C9 substrate	-	0.7872	78.72%
CYP2D6 substrate	-	0.8486	84.86%
CYP3A4 inhibition	-	0.6442	64.42%
CYP2C9 inhibition	-	0.8961	89.61%
CYP2C19 inhibition	-	0.8492	84.92%
CYP2D6 inhibition	-	0.8445	84.45%
CYP1A2 inhibition	-	0.7936	79.36%
CYP2C8 inhibition	+	0.4884	48.84%
CYP inhibitory promiscuity	-	0.9059	90.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5960	59.60%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9402	94.02%
Skin irritation	-	0.6632	66.32%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	-	0.6254	62.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7334	73.34%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.8141	81.41%
skin sensitisation	-	0.8351	83.51%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.7740	77.40%
Acute Oral Toxicity (c)	III	0.6697	66.97%
Estrogen receptor binding	+	0.8368	83.68%
Androgen receptor binding	+	0.7798	77.98%
Thyroid receptor binding	+	0.5774	57.74%
Glucocorticoid receptor binding	+	0.8528	85.28%
Aromatase binding	+	0.7005	70.05%
PPAR gamma	+	0.5846	58.46%
Honey bee toxicity	-	0.7260	72.60%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.8467	84.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.44%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.67%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.77%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.08%	97.09%
CHEMBL5028	O14672	ADAM10	88.62%	97.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.81%	94.45%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	87.58%	89.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.28%	95.50%
CHEMBL2996	Q05655	Protein kinase C delta	86.98%	97.79%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.52%	98.75%
CHEMBL2581	P07339	Cathepsin D	85.14%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	84.96%	95.93%
CHEMBL299	P17252	Protein kinase C alpha	84.66%	98.03%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.61%	95.89%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	84.18%	95.58%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	83.93%	95.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.53%	89.50%
CHEMBL221	P23219	Cyclooxygenase-1	83.45%	90.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.69%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.61%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.50%	91.19%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.48%	96.38%
CHEMBL255	P29275	Adenosine A2b receptor	82.44%	98.59%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.41%	100.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.07%	94.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.04%	91.24%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.86%	96.90%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.53%	94.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.29%	82.69%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.19%	97.50%
CHEMBL2664	P23526	Adenosylhomocysteinase	80.96%	86.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.43%	86.33%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	80.15%	95.71%

Plants that contains it

• Erythrophleum chlorostachys

Cross-Links

• PubChem: 6330379
• LOTUS: LTS0196391
• wikiData: Q105230346