[(1S,2S,3S,4S,5R,6R,8R,12R,13R,16S,19S,20S,21S)-2,6-dihydroxy-4,19-dimethoxy-14,16-dimethyl-9,11-dioxa-14-azaheptacyclo[10.7.2.12,5.01,13.03,8.08,12.016,20]docos-17-en-21-yl] acetate

Details

• Internal ID: 52d25f29-9b6e-4d83-872c-31753ac6d10d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Aconitane-type diterpenoid alkaloids
• IUPAC Name: [(1S,2S,3S,4S,5R,6R,8R,12R,13R,16S,19S,20S,21S)-2,6-dihydroxy-4,19-dimethoxy-14,16-dimethyl-9,11-dioxa-14-azaheptacyclo[10.7.2.12,5.01,13.03,8.08,12.016,20]docos-17-en-21-yl] acetate
• SMILES (Canonical): CC(=O)OC1C2C3(CN(C4C2(C(C=C3)OC)C5(CC6C(CC7(C14OCO7)C5C6OC)O)O)C)C
• SMILES (Isomeric): CC(=O)O[C@H]1[C@H]2[C@]3(CN([C@@H]4[C@@]2([C@H](C=C3)OC)[C@@]5(C[C@@H]6[C@@H](C[C@]7([C@]14OCO7)[C@H]5[C@H]6OC)O)O)C)C
• InChI: InChI=1S/C25H35NO8/c1-12(27)34-19-18-21(2)7-6-15(30-4)24(18)20(26(3)10-21)25(19)23(32-11-33-25)9-14(28)13-8-22(24,29)17(23)16(13)31-5/h6-7,13-20,28-29H,8-11H2,1-5H3/t13-,14-,15+,16+,17+,18+,19+,20-,21-,22+,23-,24+,25+/m1/s1
• InChI Key: YIRIOYAORYKQRE-BXSHUTGGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₅NO₈
• Molecular Weight: 477.50 g/mol
• Exact Mass: 477.23626707 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 0.08
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7113	71.13%
Caco-2	-	0.6414	64.14%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Lysosomes	0.6115	61.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8859	88.59%
OATP1B3 inhibitior	+	0.9437	94.37%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6914	69.14%
P-glycoprotein inhibitior	-	0.6139	61.39%
P-glycoprotein substrate	+	0.5880	58.80%
CYP3A4 substrate	+	0.7243	72.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8252	82.52%
CYP3A4 inhibition	-	0.8682	86.82%
CYP2C9 inhibition	-	0.9031	90.31%
CYP2C19 inhibition	-	0.8422	84.22%
CYP2D6 inhibition	-	0.8923	89.23%
CYP1A2 inhibition	-	0.9000	90.00%
CYP2C8 inhibition	-	0.5959	59.59%
CYP inhibitory promiscuity	-	0.9327	93.27%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4497	44.97%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.9398	93.98%
Skin irritation	-	0.7848	78.48%
Skin corrosion	-	0.9315	93.15%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6594	65.94%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.5051	50.51%
skin sensitisation	-	0.8388	83.88%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.7310	73.10%
Acute Oral Toxicity (c)	III	0.5322	53.22%
Estrogen receptor binding	+	0.8119	81.19%
Androgen receptor binding	+	0.7456	74.56%
Thyroid receptor binding	+	0.6177	61.77%
Glucocorticoid receptor binding	+	0.6239	62.39%
Aromatase binding	+	0.5959	59.59%
PPAR gamma	+	0.7141	71.41%
Honey bee toxicity	-	0.6069	60.69%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	-	0.4733	47.33%

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	98.81%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.14%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	97.17%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.69%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.95%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.42%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.41%	96.77%
CHEMBL2581	P07339	Cathepsin D	90.16%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.39%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.64%	89.00%
CHEMBL4208	P20618	Proteasome component C5	85.92%	90.00%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	85.35%	87.67%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.31%	89.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.21%	97.28%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.92%	91.24%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.54%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.92%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.80%	86.33%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.79%	81.11%
CHEMBL340	P08684	Cytochrome P450 3A4	80.70%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.05%	97.09%

Plants that contains it

• Delphinium siwanense

Cross-Links

• PubChem: 163106726
• LOTUS: LTS0098576
• wikiData: Q105349004