[(1R,5R,8R,9S,11S,13R,14R,16R,17R,18S,19R)-19-acetyloxy-11,16-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-13-yl] 2-methylpropanoate

Details

• Internal ID: 8e2a4ae7-019e-4ece-b094-85d777888607
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Villanovane, atisane, trachylobane or helvifulvane diterpenoids > Atisane diterpenoids > Hetisine-type diterpenoid alkaloids
• IUPAC Name: [(1R,5R,8R,9S,11S,13R,14R,16R,17R,18S,19R)-19-acetyloxy-11,16-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-13-yl] 2-methylpropanoate
• SMILES (Canonical): CC(C)C(=O)OC1C(=C)C2(CC3C14CC5(C6C7(CCCC6(C4C2OC(=O)C)C3N5C7)C)O)O
• SMILES (Isomeric): CC(C)C(=O)O[C@H]1C(=C)[C@]2(C[C@H]3[C@@]14C[C@]5([C@@H]6[C@]7(CCC[C@]6([C@@H]4[C@H]2OC(=O)C)[C@@H]3N5C7)C)O)O
• InChI: InChI=1S/C26H35NO6/c1-12(2)20(29)33-18-13(3)25(30)9-15-17-23-8-6-7-22(5)11-27(17)26(31,21(22)23)10-24(15,18)16(23)19(25)32-14(4)28/h12,15-19,21,30-31H,3,6-11H2,1-2,4-5H3/t15-,16+,17-,18+,19-,21-,22+,23+,24-,25+,26-/m1/s1
• InChI Key: MAOMVWHXLLFHSI-DDEBXCSHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₅NO₆
• Molecular Weight: 457.60 g/mol
• Exact Mass: 457.24643784 g/mol
• Topological Polar Surface Area (TPSA): 96.30 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.01
• H-Bond Acceptor: 7
• 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	+	0.9384	93.84%
Caco-2	-	0.6313	63.13%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6167	61.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8666	86.66%
OATP1B3 inhibitior	+	0.9215	92.15%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.6876	68.76%
P-glycoprotein inhibitior	-	0.5288	52.88%
P-glycoprotein substrate	-	0.6051	60.51%
CYP3A4 substrate	+	0.6877	68.77%
CYP2C9 substrate	-	0.7984	79.84%
CYP2D6 substrate	-	0.8629	86.29%
CYP3A4 inhibition	-	0.9283	92.83%
CYP2C9 inhibition	-	0.8181	81.81%
CYP2C19 inhibition	-	0.8462	84.62%
CYP2D6 inhibition	-	0.9297	92.97%
CYP1A2 inhibition	-	0.8737	87.37%
CYP2C8 inhibition	-	0.5817	58.17%
CYP inhibitory promiscuity	-	0.9253	92.53%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5020	50.20%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9143	91.43%
Skin irritation	-	0.7092	70.92%
Skin corrosion	-	0.9188	91.88%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4555	45.55%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.5416	54.16%
skin sensitisation	-	0.8578	85.78%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.6403	64.03%
Acute Oral Toxicity (c)	III	0.6061	60.61%
Estrogen receptor binding	+	0.7184	71.84%
Androgen receptor binding	+	0.7433	74.33%
Thyroid receptor binding	+	0.5707	57.07%
Glucocorticoid receptor binding	+	0.6589	65.89%
Aromatase binding	+	0.7108	71.08%
PPAR gamma	+	0.6616	66.16%
Honey bee toxicity	-	0.6600	66.00%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5755	57.55%
Fish aquatic toxicity	+	0.9790	97.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.24%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.41%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.15%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	91.91%	91.19%
CHEMBL2581	P07339	Cathepsin D	89.29%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.18%	91.11%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.94%	95.50%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	87.73%	95.71%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	86.59%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.36%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.04%	96.61%
CHEMBL204	P00734	Thrombin	84.68%	96.01%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.54%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	84.31%	94.75%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	83.63%	98.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.00%	95.56%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.55%	89.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.30%	97.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.13%	82.69%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.97%	91.07%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.70%	96.47%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.68%	91.24%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	81.42%	95.36%
CHEMBL268	P43235	Cathepsin K	81.21%	96.85%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.00%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.91%	95.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.86%	85.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.82%	96.38%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.73%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.38%	93.00%
CHEMBL5028	O14672	ADAM10	80.25%	97.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.07%	96.77%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.00%	82.50%

Plants that contains it

• Delphinium gracile

Cross-Links

• PubChem: 162922639
• LOTUS: LTS0003400
• wikiData: Q105160452