[(6S,7R,8R,11R,12S,14R,15S,16R)-15-[(1S)-1-(dimethylamino)ethyl]-7-(hydroxymethyl)-7,12,16-trimethyl-6-[[(E)-2-methylbut-2-enoyl]amino]-14-tetracyclo[9.7.0.03,8.012,16]octadeca-1(18),2-dienyl] acetate

Details

• Internal ID: 0f5d6ee6-e7af-45aa-a533-3f0e7bec619d
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Buxus alkaloids
• IUPAC Name: [(6S,7R,8R,11R,12S,14R,15S,16R)-15-[(1S)-1-(dimethylamino)ethyl]-7-(hydroxymethyl)-7,12,16-trimethyl-6-[[(E)-2-methylbut-2-enoyl]amino]-14-tetracyclo[9.7.0.03,8.012,16]octadeca-1(18),2-dienyl] acetate
• SMILES (Canonical): CC=C(C)C(=O)NC1CCC2=CC3=CCC4(C(C(CC4(C3CCC2C1(C)CO)C)OC(=O)C)C(C)N(C)C)C
• SMILES (Isomeric): C/C=C(\C)/C(=O)N[C@H]1CCC2=CC3=CC[C@@]4([C@H]([C@@H](C[C@]4([C@@H]3CC[C@H]2[C@@]1(C)CO)C)OC(=O)C)[C@H](C)N(C)C)C
• InChI: InChI=1S/C33H52N2O4/c1-10-20(2)30(38)34-28-14-11-23-17-24-15-16-32(6)29(21(3)35(8)9)27(39-22(4)37)18-33(32,7)26(24)13-12-25(23)31(28,5)19-36/h10,15,17,21,25-29,36H,11-14,16,18-19H2,1-9H3,(H,34,38)/b20-10+/t21-,25+,26+,27+,28-,29-,31+,32+,33-/m0/s1
• InChI Key: BRGSDABMUAIXHJ-JIXSKCAHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₂N₂O₄
• Molecular Weight: 540.80 g/mol
• Exact Mass: 540.39270814 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.43
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9307	93.07%
Caco-2	-	0.6817	68.17%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6837	68.37%
OATP2B1 inhibitior	-	0.8577	85.77%
OATP1B1 inhibitior	+	0.8222	82.22%
OATP1B3 inhibitior	+	0.9158	91.58%
MATE1 inhibitior	-	0.6544	65.44%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.9738	97.38%
P-glycoprotein inhibitior	+	0.7694	76.94%
P-glycoprotein substrate	+	0.6459	64.59%
CYP3A4 substrate	+	0.7105	71.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8353	83.53%
CYP3A4 inhibition	-	0.7980	79.80%
CYP2C9 inhibition	-	0.7129	71.29%
CYP2C19 inhibition	-	0.8016	80.16%
CYP2D6 inhibition	-	0.8839	88.39%
CYP1A2 inhibition	-	0.8630	86.30%
CYP2C8 inhibition	+	0.5153	51.53%
CYP inhibitory promiscuity	-	0.7261	72.61%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6310	63.10%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.9479	94.79%
Skin irritation	-	0.7408	74.08%
Skin corrosion	-	0.9190	91.90%
Ames mutagenesis	-	0.5924	59.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7526	75.26%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.5113	51.13%
skin sensitisation	-	0.8546	85.46%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.6690	66.90%
Acute Oral Toxicity (c)	III	0.6117	61.17%
Estrogen receptor binding	+	0.7332	73.32%
Androgen receptor binding	+	0.7359	73.59%
Thyroid receptor binding	+	0.5786	57.86%
Glucocorticoid receptor binding	+	0.8071	80.71%
Aromatase binding	+	0.7304	73.04%
PPAR gamma	+	0.6955	69.55%
Honey bee toxicity	-	0.7288	72.88%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9768	97.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.58%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.73%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.71%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.16%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	89.42%	90.17%
CHEMBL340	P08684	Cytochrome P450 3A4	88.34%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.96%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.65%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.86%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.48%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.44%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.05%	94.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.95%	95.89%
CHEMBL4040	P28482	MAP kinase ERK2	83.81%	83.82%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.19%	91.24%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.68%	95.56%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.87%	98.75%
CHEMBL226	P30542	Adenosine A1 receptor	80.65%	95.93%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	80.30%	91.65%

Plants that contains it

• Buxus sempervirens

Cross-Links

• PubChem: 162904692
• LOTUS: LTS0117018
• wikiData: Q104944791