(1S,2R,3R,4S,5S,6S,8S,9S,10R,13S,16S,17R)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecane-4,8-diol

Details

• Internal ID: 128a35b2-b72a-4d69-a1b7-988a9c051e16
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Aconitane-type diterpenoid alkaloids
• IUPAC Name: (1S,2R,3R,4S,5S,6S,8S,9S,10R,13S,16S,17R)-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecane-4,8-diol
• SMILES (Canonical): CCN1CC2(CCC(C34C2CC(C31)C5(CC(C6CC4C5C6O)OC)O)OC)COC
• SMILES (Isomeric): CCN1C[C@@]2(CC[C@@H]([C@@]34[C@@H]2C[C@@H]([C@H]31)[C@]5(C[C@@H]([C@H]6C[C@@H]4[C@@H]5[C@H]6O)OC)O)OC)COC
• InChI: InChI=1S/C24H39NO5/c1-5-25-11-22(12-28-2)7-6-18(30-4)24-14-8-13-16(29-3)10-23(27,19(14)20(13)26)15(21(24)25)9-17(22)24/h13-21,26-27H,5-12H2,1-4H3/t13-,14-,15+,16+,17-,18+,19-,20+,21-,22+,23+,24-/m1/s1
• InChI Key: BDCURAWBZJMFIK-OGVVJMRYSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₉NO₅
• Molecular Weight: 421.60 g/mol
• Exact Mass: 421.28282334 g/mol
• Topological Polar Surface Area (TPSA): 71.40 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• Talatizamine
• 20501-56-8
• C24-H39-N-O5
• (1S,4S,5R,7S,8S,9R,10R, 11S,13S,14S,16S,17R)-N-methyl- 8,14-dihydroxy-1,16-trimethoxy-4-(methoxymethylene)aconitane

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8399	83.99%
Caco-2	-	0.5303	53.03%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Lysosomes	0.7408	74.08%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.9263	92.63%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.5872	58.72%
P-glycoprotein inhibitior	-	0.8949	89.49%
P-glycoprotein substrate	+	0.6327	63.27%
CYP3A4 substrate	+	0.6905	69.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4514	45.14%
CYP3A4 inhibition	-	0.9356	93.56%
CYP2C9 inhibition	-	0.8984	89.84%
CYP2C19 inhibition	-	0.8889	88.89%
CYP2D6 inhibition	-	0.9224	92.24%
CYP1A2 inhibition	-	0.9230	92.30%
CYP2C8 inhibition	+	0.5847	58.47%
CYP inhibitory promiscuity	-	0.9489	94.89%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6314	63.14%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9039	90.39%
Skin irritation	-	0.7772	77.72%
Skin corrosion	-	0.9284	92.84%
Ames mutagenesis	-	0.5970	59.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6915	69.15%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	-	0.7366	73.66%
skin sensitisation	-	0.8608	86.08%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7339	73.39%
Acute Oral Toxicity (c)	III	0.4756	47.56%
Estrogen receptor binding	+	0.7509	75.09%
Androgen receptor binding	+	0.6858	68.58%
Thyroid receptor binding	+	0.6742	67.42%
Glucocorticoid receptor binding	+	0.5384	53.84%
Aromatase binding	+	0.6770	67.70%
PPAR gamma	+	0.6087	60.87%
Honey bee toxicity	-	0.7873	78.73%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	-	0.6766	67.66%

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	99.01%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.50%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.39%	85.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	94.05%	96.38%
CHEMBL204	P00734	Thrombin	93.27%	96.01%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.47%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.42%	97.09%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	91.90%	95.58%
CHEMBL226	P30542	Adenosine A1 receptor	91.75%	95.93%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	90.77%	91.03%
CHEMBL221	P23219	Cyclooxygenase-1	90.33%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.63%	100.00%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	87.64%	98.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.30%	95.89%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	86.26%	95.36%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	85.01%	92.38%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	84.20%	95.17%
CHEMBL1871	P10275	Androgen Receptor	83.90%	96.43%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.32%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.98%	97.14%
CHEMBL3820	P35557	Hexokinase type IV	82.28%	91.96%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	82.28%	82.38%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.97%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.79%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.65%	92.62%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	81.52%	94.78%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.18%	89.62%
CHEMBL4073	P09237	Matrix metalloproteinase 7	81.11%	97.56%
CHEMBL259	P32245	Melanocortin receptor 4	80.85%	95.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.39%	94.45%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.32%	90.24%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	80.32%	95.52%
CHEMBL2581	P07339	Cathepsin D	80.23%	98.95%

Plants that contains it

• Aconitum carmichaelii
• Aconitum cochleare
• Aconitum columbianum
• Aconitum hemsleyanum
• Aconitum jaluense
• Aconitum japonicum
• Aconitum kusnezoffii
• Aconitum macrorhynchum
• Aconitum nagarum
• Aconitum nasutum
• Aconitum sczukinii
• Aconitum transsectum
• Aconitum variegatum
• Aconitum volubile var. pubescens
• Duranta erecta
• Elsholtzia stauntonii
• Radermachera boniana

Cross-Links

• PubChem: 57506227
• NPASS: NPC205595
• LOTUS: LTS0086498
• wikiData: Q104923925