methyl (1'S,2S,7'S,9'S)-9'-[(1R)-1-hydroxyethyl]-6-methoxy-3-oxospiro[1H-indole-2,6'-3-azatricyclo[5.3.1.03,8]undecane]-7'-carboxylate

Details

• Internal ID: b151b58c-139f-4975-ad5d-8cabbb38e3b6
• Taxonomy: Organoheterocyclic compounds > Quinolizidines
• IUPAC Name: methyl (1'S,2S,7'S,9'S)-9'-[(1R)-1-hydroxyethyl]-6-methoxy-3-oxospiro[1H-indole-2,6'-3-azatricyclo[5.3.1.03,8]undecane]-7'-carboxylate
• SMILES (Canonical): CC(C1CC2CC3(C1N(C2)CCC34C(=O)C5=C(N4)C=C(C=C5)OC)C(=O)OC)O
• SMILES (Isomeric): C[C@H]([C@H]1C[C@H]2C[C@@]3(C1N(C2)CC[C@@]34C(=O)C5=C(N4)C=C(C=C5)OC)C(=O)OC)O
• InChI: InChI=1S/C22H28N2O5/c1-12(25)16-8-13-10-21(20(27)29-3)18(16)24(11-13)7-6-22(21)19(26)15-5-4-14(28-2)9-17(15)23-22/h4-5,9,12-13,16,18,23,25H,6-8,10-11H2,1-3H3/t12-,13+,16-,18?,21-,22-/m1/s1
• InChI Key: JHHVBOHRLGSLAJ-CISRQMPOSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈N₂O₅
• Molecular Weight: 400.50 g/mol
• Exact Mass: 400.19982200 g/mol
• Topological Polar Surface Area (TPSA): 88.10 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.70
• 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	+	0.9089	90.89%
Caco-2	+	0.6418	64.18%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6422	64.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9286	92.86%
OATP1B3 inhibitior	+	0.9247	92.47%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6604	66.04%
P-glycoprotein inhibitior	-	0.5546	55.46%
P-glycoprotein substrate	+	0.7372	73.72%
CYP3A4 substrate	+	0.6741	67.41%
CYP2C9 substrate	+	0.6033	60.33%
CYP2D6 substrate	-	0.7393	73.93%
CYP3A4 inhibition	-	0.8287	82.87%
CYP2C9 inhibition	-	0.8869	88.69%
CYP2C19 inhibition	-	0.8263	82.63%
CYP2D6 inhibition	-	0.6824	68.24%
CYP1A2 inhibition	-	0.8212	82.12%
CYP2C8 inhibition	-	0.8212	82.12%
CYP inhibitory promiscuity	-	0.9604	96.04%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6279	62.79%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9896	98.96%
Skin irritation	-	0.7902	79.02%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6829	68.29%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8688	86.88%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8067	80.67%
Acute Oral Toxicity (c)	III	0.5477	54.77%
Estrogen receptor binding	+	0.7464	74.64%
Androgen receptor binding	+	0.7629	76.29%
Thyroid receptor binding	+	0.5961	59.61%
Glucocorticoid receptor binding	+	0.6412	64.12%
Aromatase binding	+	0.7212	72.12%
PPAR gamma	-	0.6431	64.31%
Honey bee toxicity	-	0.7472	74.72%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.8681	86.81%

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	99.10%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.57%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.72%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.12%	98.95%
CHEMBL4208	P20618	Proteasome component C5	96.09%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.62%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.78%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.40%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	92.01%	90.71%
CHEMBL2535	P11166	Glucose transporter	89.16%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	88.66%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.54%	95.89%
CHEMBL3437	Q16853	Amine oxidase, copper containing	88.29%	94.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	87.95%	91.03%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.49%	82.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.25%	97.14%
CHEMBL4073	P09237	Matrix metalloproteinase 7	85.10%	97.56%
CHEMBL4588	P22894	Matrix metalloproteinase 8	85.08%	94.66%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.76%	96.77%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.43%	91.07%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.19%	93.03%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.73%	94.08%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.85%	94.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.03%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.53%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.27%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	80.07%	83.82%

Plants that contains it

• Tabernaemontana alternifolia

Cross-Links

• PubChem: 101133884
• LOTUS: LTS0165775
• wikiData: Q105127987