Buxalongifolamidine

Details

• Internal ID: af6e3980-28d4-4e70-9841-cd2a12e8df3a
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Buxus alkaloids
• IUPAC Name: [(3R,6S,7S,8S,11R,12S,14R,15S,16R)-6-benzamido-15-[(1S)-1-(dimethylamino)ethyl]-3-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyl-14-tetracyclo[9.7.0.03,8.012,16]octadeca-1(18),4-dienyl] acetate
• SMILES (Canonical): CC(C1C(CC2(C1(CC=C3C2CCC4C(C(C=CC4(C3)O)NC(=O)C5=CC=CC=C5)(C)CO)C)C)OC(=O)C)N(C)C
• SMILES (Isomeric): C[C@@H]([C@H]1[C@@H](C[C@@]2([C@@]1(CC=C3[C@H]2CC[C@H]4[C@]([C@H](C=C[C@@]4(C3)O)NC(=O)C5=CC=CC=C5)(C)CO)C)C)OC(=O)C)N(C)C
• InChI: InChI=1S/C35H50N2O5/c1-22(37(6)7)30-27(42-23(2)39)20-34(5)26-13-14-28-32(3,21-38)29(36-31(40)24-11-9-8-10-12-24)16-18-35(28,41)19-25(26)15-17-33(30,34)4/h8-12,15-16,18,22,26-30,38,41H,13-14,17,19-21H2,1-7H3,(H,36,40)/t22-,26+,27+,28-,29-,30-,32-,33+,34-,35-/m0/s1
• InChI Key: SQULXMOMDPJQNT-QCFSPYGNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₀N₂O₅
• Molecular Weight: 578.80 g/mol
• Exact Mass: 578.37197270 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.75
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• CHEMBL1651040
• CHEBI:70427
• BDBM50335590
• Q27138765
• 149472-47-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9312	93.12%
Caco-2	-	0.7873	78.73%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7093	70.93%
OATP2B1 inhibitior	-	0.7170	71.70%
OATP1B1 inhibitior	+	0.8638	86.38%
OATP1B3 inhibitior	+	0.9177	91.77%
MATE1 inhibitior	-	0.8272	82.72%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9899	98.99%
P-glycoprotein inhibitior	+	0.7300	73.00%
P-glycoprotein substrate	+	0.7132	71.32%
CYP3A4 substrate	+	0.7050	70.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8090	80.90%
CYP3A4 inhibition	-	0.6578	65.78%
CYP2C9 inhibition	-	0.6866	68.66%
CYP2C19 inhibition	-	0.7402	74.02%
CYP2D6 inhibition	-	0.8614	86.14%
CYP1A2 inhibition	-	0.8012	80.12%
CYP2C8 inhibition	+	0.6528	65.28%
CYP inhibitory promiscuity	-	0.6525	65.25%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6566	65.66%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9401	94.01%
Skin irritation	-	0.7479	74.79%
Skin corrosion	-	0.9246	92.46%
Ames mutagenesis	-	0.5453	54.53%
Human Ether-a-go-go-Related Gene inhibition	+	0.7509	75.09%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.5413	54.13%
skin sensitisation	-	0.8570	85.70%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.4650	46.50%
Acute Oral Toxicity (c)	III	0.6159	61.59%
Estrogen receptor binding	+	0.7753	77.53%
Androgen receptor binding	+	0.7576	75.76%
Thyroid receptor binding	+	0.5876	58.76%
Glucocorticoid receptor binding	+	0.7806	78.06%
Aromatase binding	+	0.6964	69.64%
PPAR gamma	+	0.7469	74.69%
Honey bee toxicity	-	0.7376	73.76%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9920	99.20%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	30200 nM	IC50	PMID: 20954721

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	98.80%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.74%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.20%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.23%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.45%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.06%	94.62%
CHEMBL5028	O14672	ADAM10	87.96%	97.50%
CHEMBL4072	P07858	Cathepsin B	87.86%	93.67%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.63%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.59%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.92%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.87%	99.17%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.43%	96.47%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.42%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.34%	91.07%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.22%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.98%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	84.85%	91.19%
CHEMBL1951	P21397	Monoamine oxidase A	84.29%	91.49%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.21%	94.08%
CHEMBL268	P43235	Cathepsin K	84.17%	96.85%
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	83.85%	91.43%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	83.68%	91.65%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.60%	94.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.12%	97.14%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.93%	89.67%

Plants that contains it

• Buxus balearica
• Buxus natalensis

Cross-Links

• PubChem: 53324854
• NPASS: NPC328824
• ChEMBL: CHEMBL1651040
• LOTUS: LTS0147269
• wikiData: Q27138765