methyl (1S,2S,3R,5R,10S)-2,6-dimethyl-8-oxido-21-oxo-14-oxa-8-azoniahexacyclo[11.6.1.11,5.02,10.03,8.017,20]henicosa-13(20),17-diene-18-carboxylate

Details

• Internal ID: bd4b44e7-3d6e-423a-9fcb-e59efb381331
• Taxonomy: Organoheterocyclic compounds > Indolizidines
• IUPAC Name: methyl (1S,2S,3R,5R,10S)-2,6-dimethyl-8-oxido-21-oxo-14-oxa-8-azoniahexacyclo[11.6.1.11,5.02,10.03,8.017,20]henicosa-13(20),17-diene-18-carboxylate
• SMILES (Canonical): CC1C[N+]2(CC3CCC4=C5C(=C(CC56C3(C2CC1C6=O)C)C(=O)OC)CCO4)[O-]
• SMILES (Isomeric): CC1C[N+]2(C[C@H]3CCC4=C5C(=C(C[C@]56[C@]3([C@H]2C[C@H]1C6=O)C)C(=O)OC)CCO4)[O-]
• InChI: InChI=1S/C23H29NO5/c1-12-10-24(27)11-13-4-5-17-19-14(6-7-29-17)16(21(26)28-3)9-23(19)20(25)15(12)8-18(24)22(13,23)2/h12-13,15,18H,4-11H2,1-3H3/t12?,13-,15-,18-,22-,23+,24?/m1/s1
• InChI Key: OHPSOIUFKKLGIW-LJROMOPWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₉NO₅
• Molecular Weight: 399.50 g/mol
• Exact Mass: 399.20457303 g/mol
• Topological Polar Surface Area (TPSA): 70.70 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 2.87
• 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	-	0.6144	61.44%
Caco-2	+	0.7075	70.75%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.3890	38.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8611	86.11%
OATP1B3 inhibitior	+	0.9414	94.14%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.8231	82.31%
P-glycoprotein inhibitior	-	0.6391	63.91%
P-glycoprotein substrate	+	0.5076	50.76%
CYP3A4 substrate	+	0.6987	69.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8849	88.49%
CYP3A4 inhibition	-	0.6726	67.26%
CYP2C9 inhibition	-	0.8589	85.89%
CYP2C19 inhibition	-	0.8237	82.37%
CYP2D6 inhibition	-	0.8876	88.76%
CYP1A2 inhibition	-	0.8189	81.89%
CYP2C8 inhibition	+	0.6498	64.98%
CYP inhibitory promiscuity	-	0.9486	94.86%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Danger	0.4230	42.30%
Eye corrosion	-	0.9785	97.85%
Eye irritation	-	0.8843	88.43%
Skin irritation	-	0.7628	76.28%
Skin corrosion	-	0.9168	91.68%
Ames mutagenesis	-	0.6291	62.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.4613	46.13%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8325	83.25%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.6546	65.46%
Acute Oral Toxicity (c)	III	0.6043	60.43%
Estrogen receptor binding	+	0.8087	80.87%
Androgen receptor binding	+	0.7283	72.83%
Thyroid receptor binding	-	0.5220	52.20%
Glucocorticoid receptor binding	+	0.7852	78.52%
Aromatase binding	+	0.6085	60.85%
PPAR gamma	-	0.5158	51.58%
Honey bee toxicity	-	0.7761	77.61%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9282	92.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.15%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.70%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.82%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.08%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	89.09%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.94%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.85%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.79%	92.94%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.28%	94.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.76%	91.24%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.40%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.86%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.86%	97.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.40%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.10%	95.89%
CHEMBL2581	P07339	Cathepsin D	82.46%	98.95%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.25%	93.03%
CHEMBL255	P29275	Adenosine A2b receptor	82.11%	98.59%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	81.31%	88.84%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.89%	95.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.63%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.54%	95.56%

Plants that contains it

• Daphniphyllum subverticillatum

Cross-Links

• PubChem: 137705433
• LOTUS: LTS0101818
• wikiData: Q104401017