[(1S,5R,8R,9S,10R,11S,13R,14S,16S,17R,18S,19S)-13-acetyloxy-10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-19-yl] benzoate

Details

• Internal ID: 42fece86-28b5-4f0b-80fe-45ed874057c0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Villanovane, atisane, trachylobane or helvifulvane diterpenoids > Atisane diterpenoids
• IUPAC Name: [(1S,5R,8R,9S,10R,11S,13R,14S,16S,17R,18S,19S)-13-acetyloxy-10-hydroxy-5-methyl-12-methylidene-3-oxo-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-19-yl] benzoate
• SMILES (Canonical): CC(=O)OC1C(=C)C2C(C3C14CC5C6C7(CC(=O)CC6(C4C2OC(=O)C8=CC=CC=C8)C3N5C7)C)O
• SMILES (Isomeric): CC(=O)O[C@@H]1C(=C)[C@H]2[C@@H]([C@H]3[C@@]14C[C@H]5[C@@H]6[C@]7(CC(=O)C[C@]6([C@@H]4[C@@H]2OC(=O)C8=CC=CC=C8)[C@@H]3N5C7)C)O
• InChI: InChI=1S/C29H31NO6/c1-13-18-20(33)19-24-29-10-16(32)9-27(3)12-30(24)17(22(27)29)11-28(19,25(13)35-14(2)31)23(29)21(18)36-26(34)15-7-5-4-6-8-15/h4-8,17-25,33H,1,9-12H2,2-3H3/t17-,18-,19+,20-,21+,22+,23+,24+,25+,27-,28+,29-/m0/s1
• InChI Key: XUKQBWKRCZANJN-MCMHOXFLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₁NO₆
• Molecular Weight: 489.60 g/mol
• Exact Mass: 489.21513771 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 7
• 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	+	0.9183	91.83%
Caco-2	-	0.8009	80.09%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6428	64.28%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8631	86.31%
OATP1B3 inhibitior	+	0.9244	92.44%
MATE1 inhibitior	-	0.8620	86.20%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.6194	61.94%
P-glycoprotein inhibitior	-	0.4354	43.54%
P-glycoprotein substrate	+	0.5308	53.08%
CYP3A4 substrate	+	0.6957	69.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7306	73.06%
CYP3A4 inhibition	-	0.8594	85.94%
CYP2C9 inhibition	-	0.8893	88.93%
CYP2C19 inhibition	-	0.8545	85.45%
CYP2D6 inhibition	-	0.9149	91.49%
CYP1A2 inhibition	-	0.8614	86.14%
CYP2C8 inhibition	+	0.6519	65.19%
CYP inhibitory promiscuity	-	0.7867	78.67%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4883	48.83%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9367	93.67%
Skin irritation	-	0.7527	75.27%
Skin corrosion	-	0.9342	93.42%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4132	41.32%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.5214	52.14%
skin sensitisation	-	0.8446	84.46%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.7960	79.60%
Acute Oral Toxicity (c)	III	0.5730	57.30%
Estrogen receptor binding	+	0.7392	73.92%
Androgen receptor binding	+	0.7043	70.43%
Thyroid receptor binding	-	0.5106	51.06%
Glucocorticoid receptor binding	+	0.6202	62.02%
Aromatase binding	+	0.6305	63.05%
PPAR gamma	+	0.6131	61.31%
Honey bee toxicity	-	0.7685	76.85%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9907	99.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.96%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	97.18%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.95%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.74%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.95%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.48%	91.11%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	88.81%	94.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.29%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.41%	94.62%
CHEMBL340	P08684	Cytochrome P450 3A4	84.07%	91.19%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.72%	82.69%
CHEMBL4208	P20618	Proteasome component C5	82.62%	90.00%
CHEMBL5028	O14672	ADAM10	82.40%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.15%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.60%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.12%	97.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.54%	93.03%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.05%	91.07%

Plants that contains it

• Aconitum napellus
• Delphinium verdunense

Cross-Links

• PubChem: 101933621
• LOTUS: LTS0275123
• wikiData: Q105342381