[(1S,5R,8R,9S,10S,11R,14R,16S,17S,18R,19R)-19-hydroxy-5-methyl-12-methylidene-4-oxo-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-10-yl] (2S)-2-methylbutanoate

Details

• Internal ID: e210b737-4200-42d1-b08f-2ac75df7a177
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Villanovane, atisane, trachylobane or helvifulvane diterpenoids > Atisane diterpenoids > Hetisine-type diterpenoid alkaloids
• IUPAC Name: [(1S,5R,8R,9S,10S,11R,14R,16S,17S,18R,19R)-19-hydroxy-5-methyl-12-methylidene-4-oxo-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-10-yl] (2S)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C2C(C3C45CCC(=O)C6(C4C7CC3(C1C5N7C6)CC2=C)C)O
• SMILES (Isomeric): CC[C@H](C)C(=O)O[C@@H]1[C@H]2[C@@H]([C@H]3[C@]45CCC(=O)[C@@]6([C@H]4[C@@H]7C[C@]3([C@H]1[C@H]5N7C6)CC2=C)C)O
• InChI: InChI=1S/C25H33NO4/c1-5-11(2)22(29)30-18-15-12(3)8-24-9-13-19-23(4)10-26(13)21(16(18)24)25(19,7-6-14(23)27)20(24)17(15)28/h11,13,15-21,28H,3,5-10H2,1-2,4H3/t11-,13-,15+,16+,17-,18+,19+,20+,21+,23+,24-,25-/m0/s1
• InChI Key: LQWKDKOZXSGMGH-MLSYSCIVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₃NO₄
• Molecular Weight: 411.50 g/mol
• Exact Mass: 411.24095853 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.57
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9131	91.31%
Caco-2	-	0.5363	53.63%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6078	60.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8569	85.69%
OATP1B3 inhibitior	+	0.9277	92.77%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.7065	70.65%
P-glycoprotein inhibitior	-	0.7025	70.25%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6720	67.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7264	72.64%
CYP3A4 inhibition	-	0.8891	88.91%
CYP2C9 inhibition	-	0.8821	88.21%
CYP2C19 inhibition	-	0.8894	88.94%
CYP2D6 inhibition	-	0.8553	85.53%
CYP1A2 inhibition	-	0.7777	77.77%
CYP2C8 inhibition	-	0.5734	57.34%
CYP inhibitory promiscuity	-	0.8027	80.27%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5301	53.01%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9585	95.85%
Skin irritation	-	0.6886	68.86%
Skin corrosion	-	0.9218	92.18%
Ames mutagenesis	-	0.7554	75.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5116	51.16%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	+	0.5399	53.99%
skin sensitisation	-	0.8667	86.67%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5633	56.33%
Acute Oral Toxicity (c)	III	0.7022	70.22%
Estrogen receptor binding	+	0.6696	66.96%
Androgen receptor binding	+	0.6909	69.09%
Thyroid receptor binding	+	0.5985	59.85%
Glucocorticoid receptor binding	+	0.7407	74.07%
Aromatase binding	+	0.6645	66.45%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8143	81.43%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9878	98.78%

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	98.96%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.84%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.32%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.34%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	91.65%	90.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.48%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.06%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.21%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.73%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.00%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	82.99%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.14%	86.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.61%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.55%	92.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.38%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.17%	99.23%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.87%	96.38%
CHEMBL4072	P07858	Cathepsin B	80.60%	93.67%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.27%	90.71%

Plants that contains it

• Delphinium majus

Cross-Links

• PubChem: 163104936
• LOTUS: LTS0250615
• wikiData: Q105155928