[(1S,2R,5S,7R,8R,12S,13S,18R,20S)-12-methyl-4-methylidene-14,19-dioxa-17-azaheptacyclo[10.7.2.22,5.02,7.08,18.08,21.013,17]tricosan-20-yl] acetate

Details

• Internal ID: b724836f-f905-468a-b5ca-01f399d2ca83
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Villanovane, atisane, trachylobane or helvifulvane diterpenoids > Atisane diterpenoids
• IUPAC Name: [(1S,2R,5S,7R,8R,12S,13S,18R,20S)-12-methyl-4-methylidene-14,19-dioxa-17-azaheptacyclo[10.7.2.22,5.02,7.08,18.08,21.013,17]tricosan-20-yl] acetate
• SMILES (Canonical): CC(=O)OC1C2C3(CCCC24C5CC6CCC5(C1OC4N7C3OCC7)CC6=C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@@H]2[C@@]34CC[C@@H](C[C@H]3[C@@]56C1[C@](CCC5)([C@H]7N([C@@H]6O2)CCO7)C)C(=C)C4
• InChI: InChI=1S/C24H33NO4/c1-13-12-23-8-5-15(13)11-16(23)24-7-4-6-22(3)18(24)17(28-14(2)26)19(23)29-21(24)25-9-10-27-20(22)25/h15-21H,1,4-12H2,2-3H3/t15-,16+,17-,18?,19+,20-,21+,22-,23+,24+/m0/s1
• InChI Key: HSZMQRORNAEJTB-ZAMCDJGJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₃NO₄
• Molecular Weight: 399.50 g/mol
• Exact Mass: 399.24095853 g/mol
• Topological Polar Surface Area (TPSA): 48.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.48
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9587	95.87%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.4561	45.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8535	85.35%
OATP1B3 inhibitior	+	0.9335	93.35%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.7048	70.48%
P-glycoprotein inhibitior	-	0.5360	53.60%
P-glycoprotein substrate	-	0.5382	53.82%
CYP3A4 substrate	+	0.7138	71.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8541	85.41%
CYP3A4 inhibition	-	0.8262	82.62%
CYP2C9 inhibition	-	0.9055	90.55%
CYP2C19 inhibition	-	0.8590	85.90%
CYP2D6 inhibition	-	0.9189	91.89%
CYP1A2 inhibition	-	0.8079	80.79%
CYP2C8 inhibition	+	0.4561	45.61%
CYP inhibitory promiscuity	-	0.7057	70.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4728	47.28%
Eye corrosion	-	0.9838	98.38%
Eye irritation	-	0.9345	93.45%
Skin irritation	-	0.7551	75.51%
Skin corrosion	-	0.8986	89.86%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7211	72.11%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.6584	65.84%
skin sensitisation	-	0.8279	82.79%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6339	63.39%
Acute Oral Toxicity (c)	III	0.7075	70.75%
Estrogen receptor binding	+	0.7181	71.81%
Androgen receptor binding	+	0.7215	72.15%
Thyroid receptor binding	-	0.5085	50.85%
Glucocorticoid receptor binding	+	0.7156	71.56%
Aromatase binding	+	0.5927	59.27%
PPAR gamma	+	0.6017	60.17%
Honey bee toxicity	-	0.7361	73.61%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9093	90.93%

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	95.93%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.44%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.74%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.71%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.93%	82.69%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	92.45%	93.04%
CHEMBL340	P08684	Cytochrome P450 3A4	90.20%	91.19%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.49%	95.50%
CHEMBL5028	O14672	ADAM10	87.02%	97.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.81%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.80%	86.33%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.54%	96.38%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.42%	92.94%
CHEMBL2581	P07339	Cathepsin D	86.12%	98.95%
CHEMBL3474	P14555	Phospholipase A2 group IIA	83.23%	94.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.47%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	82.44%	92.50%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.27%	90.24%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.99%	85.14%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.45%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.42%	93.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.12%	97.14%

Plants that contains it

• Hyoscyamus niger
• Spiraea japonica

Cross-Links

• PubChem: 138113922
• LOTUS: LTS0222478
• wikiData: Q105169991