[(1S,4S,5R,6S,8R,9R,13S,16S,18S)-11-ethyl-8,9-dihydroxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl]methyl 2-aminobenzoate

Details

• Internal ID: 374873d8-564a-41b4-9ce8-857df00f100d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Aconitane-type diterpenoid alkaloids
• IUPAC Name: [(1S,4S,5R,6S,8R,9R,13S,16S,18S)-11-ethyl-8,9-dihydroxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl]methyl 2-aminobenzoate
• SMILES (Canonical): CCN1CC2(CCC(C34C2C(C(C31)(C5(CC(C6CC4C5C6OC)OC)O)O)OC)OC)COC(=O)C7=CC=CC=C7N
• SMILES (Isomeric): CCN1C[C@@]2(CC[C@@H]([C@@]34C2[C@@H]([C@](C31)([C@]5(C[C@@H]([C@H]6CC4C5[C@H]6OC)OC)O)O)OC)OC)COC(=O)C7=CC=CC=C7N
• InChI: InChI=1S/C32H46N2O8/c1-6-34-15-29(16-42-27(35)17-9-7-8-10-20(17)33)12-11-22(39-3)31-19-13-18-21(38-2)14-30(36,23(19)24(18)40-4)32(37,28(31)34)26(41-5)25(29)31/h7-10,18-19,21-26,28,36-37H,6,11-16,33H2,1-5H3/t18-,19?,21+,22+,23?,24+,25?,26+,28?,29+,30-,31+,32+/m1/s1
• InChI Key: NNDHDYDFEDRMGH-ZPGZUGTNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₆N₂O₈
• Molecular Weight: 586.70 g/mol
• Exact Mass: 586.32541643 g/mol
• Topological Polar Surface Area (TPSA): 133.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.72
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• CHEMBL359227
• BDBM50054814

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4900	49.00%
Caco-2	-	0.7957	79.57%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Lysosomes	0.5726	57.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8804	88.04%
OATP1B3 inhibitior	+	0.9386	93.86%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9831	98.31%
P-glycoprotein inhibitior	+	0.6122	61.22%
P-glycoprotein substrate	+	0.7445	74.45%
CYP3A4 substrate	+	0.7231	72.31%
CYP2C9 substrate	-	0.5881	58.81%
CYP2D6 substrate	-	0.7875	78.75%
CYP3A4 inhibition	-	0.8535	85.35%
CYP2C9 inhibition	-	0.9050	90.50%
CYP2C19 inhibition	-	0.8772	87.72%
CYP2D6 inhibition	-	0.8180	81.80%
CYP1A2 inhibition	-	0.8648	86.48%
CYP2C8 inhibition	+	0.7593	75.93%
CYP inhibitory promiscuity	-	0.9549	95.49%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6170	61.70%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9285	92.85%
Skin irritation	-	0.7750	77.50%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	-	0.7370	73.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7316	73.16%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	-	0.6317	63.17%
skin sensitisation	-	0.8601	86.01%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8946	89.46%
Acute Oral Toxicity (c)	III	0.5470	54.70%
Estrogen receptor binding	+	0.8352	83.52%
Androgen receptor binding	+	0.7660	76.60%
Thyroid receptor binding	+	0.6078	60.78%
Glucocorticoid receptor binding	+	0.5657	56.57%
Aromatase binding	+	0.7491	74.91%
PPAR gamma	+	0.7621	76.21%
Honey bee toxicity	-	0.7498	74.98%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.7892	78.92%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	79.4 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.69%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.82%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	97.47%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.30%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.31%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.23%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	89.35%	95.93%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.38%	82.69%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.18%	89.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.57%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.18%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.92%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.29%	95.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.18%	93.03%
CHEMBL5028	O14672	ADAM10	81.36%	97.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.87%	94.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.13%	100.00%

Plants that contains it

• Allium sativum
• Arctium lappa
• Cynara cardunculus
• Galinsoga parviflora
• Platycodon grandiflorus
• Sphenoclea zeylanica
• Taraxacum officinale

Cross-Links

• PubChem: 44363234
• LOTUS: LTS0153720
• wikiData: Q104395236