(2R)-N-[(6S,7S,8R,11R,12S,15S,16R)-15-[(1S)-1-(dimethylamino)ethyl]-7-(hydroxymethyl)-7,12,16-trimethyl-6-tetracyclo[9.7.0.03,8.012,16]octadeca-1(18),2-dienyl]-2-hydroxy-N,3-dimethylbutanamide

Details

• Internal ID: 0668dcc6-b861-4579-ac69-30835c472f1c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Buxus alkaloids
• IUPAC Name: (2R)-N-[(6S,7S,8R,11R,12S,15S,16R)-15-[(1S)-1-(dimethylamino)ethyl]-7-(hydroxymethyl)-7,12,16-trimethyl-6-tetracyclo[9.7.0.03,8.012,16]octadeca-1(18),2-dienyl]-2-hydroxy-N,3-dimethylbutanamide
• SMILES (Canonical): CC(C)C(C(=O)N(C)C1CCC2=CC3=CCC4(C(CCC4(C3CCC2C1(C)CO)C)C(C)N(C)C)C)O
• SMILES (Isomeric): C[C@@H]([C@H]1CC[C@@]2([C@@]1(CC=C3[C@H]2CC[C@@H]4C(=C3)CC[C@@H]([C@@]4(C)CO)N(C)C(=O)[C@@H](C(C)C)O)C)C)N(C)C
• InChI: InChI=1S/C32H54N2O3/c1-20(2)28(36)29(37)34(9)27-13-10-22-18-23-14-16-31(5)24(21(3)33(7)8)15-17-32(31,6)26(23)12-11-25(22)30(27,4)19-35/h14,18,20-21,24-28,35-36H,10-13,15-17,19H2,1-9H3/t21-,24+,25+,26+,27-,28+,30-,31+,32-/m0/s1
• InChI Key: WQUVNLRFMHVSNA-JNUNAGPTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₅₄N₂O₃
• Molecular Weight: 514.80 g/mol
• Exact Mass: 514.41344359 g/mol
• Topological Polar Surface Area (TPSA): 64.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.28
• H-Bond Acceptor: 4
• 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	+	0.9431	94.31%
Caco-2	-	0.5596	55.96%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6769	67.69%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8485	84.85%
OATP1B3 inhibitior	+	0.9362	93.62%
MATE1 inhibitior	-	0.9310	93.10%
OCT2 inhibitior	-	0.6278	62.78%
BSEP inhibitior	+	0.9550	95.50%
P-glycoprotein inhibitior	+	0.6224	62.24%
P-glycoprotein substrate	+	0.6020	60.20%
CYP3A4 substrate	+	0.6765	67.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7469	74.69%
CYP3A4 inhibition	-	0.7429	74.29%
CYP2C9 inhibition	-	0.7001	70.01%
CYP2C19 inhibition	-	0.7619	76.19%
CYP2D6 inhibition	-	0.7946	79.46%
CYP1A2 inhibition	-	0.7993	79.93%
CYP2C8 inhibition	-	0.6121	61.21%
CYP inhibitory promiscuity	-	0.5480	54.80%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.6243	62.43%
Eye corrosion	-	0.9812	98.12%
Eye irritation	-	0.9466	94.66%
Skin irritation	-	0.7471	74.71%
Skin corrosion	-	0.9009	90.09%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6970	69.70%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	-	0.5013	50.13%
skin sensitisation	-	0.8181	81.81%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.7389	73.89%
Acute Oral Toxicity (c)	III	0.6199	61.99%
Estrogen receptor binding	+	0.7850	78.50%
Androgen receptor binding	+	0.7631	76.31%
Thyroid receptor binding	+	0.6413	64.13%
Glucocorticoid receptor binding	+	0.7840	78.40%
Aromatase binding	+	0.6475	64.75%
PPAR gamma	+	0.5490	54.90%
Honey bee toxicity	-	0.8356	83.56%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9564	95.64%

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	98.84%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.52%	97.25%
CHEMBL2581	P07339	Cathepsin D	95.79%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.85%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.25%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.35%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.20%	90.71%
CHEMBL268	P43235	Cathepsin K	86.61%	96.85%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.08%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	85.86%	90.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.57%	94.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	85.21%	90.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.86%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.85%	95.89%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.77%	98.75%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.74%	85.11%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.27%	100.00%

Plants that contains it

• Buxus papillosa

Cross-Links

• PubChem: 5478953
• LOTUS: LTS0117957
• wikiData: Q105311009