methyl (3S,4S,5R,6R,9R)-3,6-dihydroxy-2,10-dioxo-11,21-diazapentacyclo[12.7.0.03,11.04,9.015,20]henicosa-1(14),15,17,19-tetraene-5-carboxylate

Details

• Internal ID: 93ab88d1-032f-4ff8-9f1d-8c7bc240695d
• Taxonomy: Organoheterocyclic compounds > Pyrroloazepines
• IUPAC Name: methyl (3S,4S,5R,6R,9R)-3,6-dihydroxy-2,10-dioxo-11,21-diazapentacyclo[12.7.0.03,11.04,9.015,20]henicosa-1(14),15,17,19-tetraene-5-carboxylate
• SMILES (Canonical): COC(=O)C1C(CCC2C1C3(C(=O)C4=C(CCN3C2=O)C5=CC=CC=C5N4)O)O
• SMILES (Isomeric): COC(=O)[C@H]1[C@@H](CC[C@@H]2[C@@H]1[C@@]3(C(=O)C4=C(CCN3C2=O)C5=CC=CC=C5N4)O)O
• InChI: InChI=1S/C21H22N2O6/c1-29-20(27)15-14(24)7-6-12-16(15)21(28)18(25)17-11(8-9-23(21)19(12)26)10-4-2-3-5-13(10)22-17/h2-5,12,14-16,22,24,28H,6-9H2,1H3/t12-,14-,15+,16+,21+/m1/s1
• InChI Key: IIBGFVKPIHLAEW-DYRGRVSNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂N₂O₆
• Molecular Weight: 398.40 g/mol
• Exact Mass: 398.14778643 g/mol
• Topological Polar Surface Area (TPSA): 120.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.61
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5990	59.90%
Caco-2	+	0.4891	48.91%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6152	61.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8760	87.60%
OATP1B3 inhibitior	+	0.9285	92.85%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7776	77.76%
P-glycoprotein inhibitior	-	0.6090	60.90%
P-glycoprotein substrate	+	0.6377	63.77%
CYP3A4 substrate	+	0.7292	72.92%
CYP2C9 substrate	-	0.7931	79.31%
CYP2D6 substrate	-	0.8345	83.45%
CYP3A4 inhibition	-	0.6075	60.75%
CYP2C9 inhibition	-	0.7453	74.53%
CYP2C19 inhibition	-	0.7523	75.23%
CYP2D6 inhibition	-	0.9193	91.93%
CYP1A2 inhibition	-	0.8394	83.94%
CYP2C8 inhibition	+	0.5431	54.31%
CYP inhibitory promiscuity	-	0.6528	65.28%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6161	61.61%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9662	96.62%
Skin irritation	-	0.8099	80.99%
Skin corrosion	-	0.9458	94.58%
Ames mutagenesis	-	0.6470	64.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4097	40.97%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8999	89.99%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.7204	72.04%
Acute Oral Toxicity (c)	III	0.5619	56.19%
Estrogen receptor binding	+	0.7701	77.01%
Androgen receptor binding	+	0.7616	76.16%
Thyroid receptor binding	-	0.5728	57.28%
Glucocorticoid receptor binding	+	0.6900	69.00%
Aromatase binding	-	0.5404	54.04%
PPAR gamma	-	0.5188	51.88%
Honey bee toxicity	-	0.8550	85.50%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	-	0.5074	50.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.52%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.87%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.85%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.24%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.85%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.11%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.01%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.57%	99.23%
CHEMBL255	P29275	Adenosine A2b receptor	88.09%	98.59%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.92%	93.03%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	86.42%	94.23%
CHEMBL5028	O14672	ADAM10	85.66%	97.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.48%	94.08%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	84.87%	92.67%
CHEMBL3310	Q96DB2	Histone deacetylase 11	84.48%	88.56%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.83%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.68%	89.00%
CHEMBL4040	P28482	MAP kinase ERK2	82.84%	83.82%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.83%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.53%	95.83%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.40%	90.08%
CHEMBL4208	P20618	Proteasome component C5	80.25%	90.00%

Plants that contains it

• Crinum asiaticum

Cross-Links

• PubChem: 101894431
• NPASS: NPC152569