methyl (1R,9R,12R,21S)-4-methoxy-20-oxo-19-oxa-8,16-diazahexacyclo[10.6.4.01,9.02,7.09,21.012,16]docosa-2(7),3,5,13-tetraene-8-carboxylate

Details

• Internal ID: 560355e1-932e-459a-b097-5df281134d61
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indolecarboxylic acids and derivatives > Indolecarboxylic acids
• IUPAC Name: methyl (1R,9R,12R,21S)-4-methoxy-20-oxo-19-oxa-8,16-diazahexacyclo[10.6.4.01,9.02,7.09,21.012,16]docosa-2(7),3,5,13-tetraene-8-carboxylate
• SMILES (Canonical): COC1=CC2=C(C=C1)N(C34C25CCN6CC=CC6(CC3)CC4C(=O)O5)C(=O)OC
• SMILES (Isomeric): COC1=CC2=C(C=C1)N([C@]34[C@@]25CCN6CC=C[C@@]6(CC3)C[C@@H]4C(=O)O5)C(=O)OC
• InChI: InChI=1S/C22H24N2O5/c1-27-14-4-5-17-15(12-14)22-9-11-23-10-3-6-20(23)7-8-21(22,24(17)19(26)28-2)16(13-20)18(25)29-22/h3-6,12,16H,7-11,13H2,1-2H3/t16-,20-,21-,22-/m1/s1
• InChI Key: WIRDHJSGFBXCLT-XUFNMVPLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₄N₂O₅
• Molecular Weight: 396.40 g/mol
• Exact Mass: 396.16852187 g/mol
• Topological Polar Surface Area (TPSA): 68.30 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.59
• H-Bond Acceptor: 6
• 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	+	0.9794	97.94%
Caco-2	+	0.7050	70.50%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5709	57.09%
OATP2B1 inhibitior	-	0.8577	85.77%
OATP1B1 inhibitior	+	0.8759	87.59%
OATP1B3 inhibitior	+	0.9374	93.74%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8979	89.79%
P-glycoprotein inhibitior	+	0.7742	77.42%
P-glycoprotein substrate	+	0.5233	52.33%
CYP3A4 substrate	+	0.6872	68.72%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	+	0.3798	37.98%
CYP3A4 inhibition	+	0.5880	58.80%
CYP2C9 inhibition	-	0.7184	71.84%
CYP2C19 inhibition	-	0.5141	51.41%
CYP2D6 inhibition	-	0.9206	92.06%
CYP1A2 inhibition	-	0.8110	81.10%
CYP2C8 inhibition	-	0.6513	65.13%
CYP inhibitory promiscuity	-	0.6400	64.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5189	51.89%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9639	96.39%
Skin irritation	-	0.8325	83.25%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7819	78.19%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.5335	53.35%
skin sensitisation	-	0.8659	86.59%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6349	63.49%
Acute Oral Toxicity (c)	III	0.6723	67.23%
Estrogen receptor binding	+	0.7886	78.86%
Androgen receptor binding	+	0.7633	76.33%
Thyroid receptor binding	+	0.5170	51.70%
Glucocorticoid receptor binding	+	0.7125	71.25%
Aromatase binding	+	0.6132	61.32%
PPAR gamma	-	0.5214	52.14%
Honey bee toxicity	-	0.8668	86.68%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9684	96.84%

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	98.99%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.35%	91.11%
CHEMBL4208	P20618	Proteasome component C5	95.91%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.91%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.85%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.40%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.61%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.49%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.12%	92.62%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	86.98%	92.67%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.38%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.68%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	85.59%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.57%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.05%	97.14%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	84.85%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.29%	95.89%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	83.29%	89.05%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.37%	95.71%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.36%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.03%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.70%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.14%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.83%	92.94%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.45%	91.03%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.36%	94.42%

Plants that contains it

• Kopsia tenuis

Cross-Links

• PubChem: 101354335
• LOTUS: LTS0062214
• wikiData: Q105306454