dimethyl (1R,9R,16R,18S,21S)-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.19,12.01,9.03,8.016,21]henicosa-3(8),4,6-triene-2,18-dicarboxylate

Details

• Internal ID: efd07a19-1d58-41a8-babc-7eb4678ec3a7
• Taxonomy: Alkaloids and derivatives > Aspidofractine alkaloids
• IUPAC Name: dimethyl (1R,9R,16R,18S,21S)-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.19,12.01,9.03,8.016,21]henicosa-3(8),4,6-triene-2,18-dicarboxylate
• SMILES (Canonical): COC1=C(C2=C(C=C1)C34CCN5C3C6(CCC5)CCC4(N2C(=O)OC)C(C6)C(=O)OC)OC
• SMILES (Isomeric): COC1=C(C2=C(C=C1)[C@]34CCN5[C@H]3[C@]6(CCC5)CC[C@@]4(N2C(=O)OC)[C@H](C6)C(=O)OC)OC
• InChI: InChI=1S/C25H32N2O6/c1-30-17-7-6-15-18(19(17)31-2)27(22(29)33-4)25-10-9-23(14-16(25)20(28)32-3)8-5-12-26-13-11-24(15,25)21(23)26/h6-7,16,21H,5,8-14H2,1-4H3/t16-,21+,23-,24-,25-/m1/s1
• InChI Key: NQKHZSNXAUQSHC-XHMWRUPGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂N₂O₆
• Molecular Weight: 456.50 g/mol
• Exact Mass: 456.22603674 g/mol
• Topological Polar Surface Area (TPSA): 77.50 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.11
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8870	88.70%
Caco-2	+	0.6909	69.09%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6327	63.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9016	90.16%
OATP1B3 inhibitior	+	0.9281	92.81%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8551	85.51%
P-glycoprotein inhibitior	+	0.6719	67.19%
P-glycoprotein substrate	+	0.5635	56.35%
CYP3A4 substrate	+	0.6749	67.49%
CYP2C9 substrate	-	0.7869	78.69%
CYP2D6 substrate	+	0.4427	44.27%
CYP3A4 inhibition	+	0.5180	51.80%
CYP2C9 inhibition	-	0.7802	78.02%
CYP2C19 inhibition	-	0.5739	57.39%
CYP2D6 inhibition	-	0.7245	72.45%
CYP1A2 inhibition	-	0.7102	71.02%
CYP2C8 inhibition	-	0.6083	60.83%
CYP inhibitory promiscuity	-	0.6200	62.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5844	58.44%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9466	94.66%
Skin irritation	-	0.8162	81.62%
Skin corrosion	-	0.9495	94.95%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7031	70.31%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.5698	56.98%
skin sensitisation	-	0.8883	88.83%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.6100	61.00%
Acute Oral Toxicity (c)	III	0.5898	58.98%
Estrogen receptor binding	+	0.7420	74.20%
Androgen receptor binding	+	0.7492	74.92%
Thyroid receptor binding	-	0.4924	49.24%
Glucocorticoid receptor binding	+	0.6831	68.31%
Aromatase binding	+	0.6006	60.06%
PPAR gamma	+	0.5988	59.88%
Honey bee toxicity	-	0.8330	83.30%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5174	51.74%
Fish aquatic toxicity	+	0.9515	95.15%

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	97.71%	96.09%
CHEMBL4208	P20618	Proteasome component C5	91.76%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.50%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.21%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.70%	94.45%
CHEMBL2581	P07339	Cathepsin D	85.85%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.57%	94.00%
CHEMBL4040	P28482	MAP kinase ERK2	84.97%	83.82%
CHEMBL5028	O14672	ADAM10	84.00%	97.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.81%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.10%	99.23%

Plants that contains it

• Kopsia griffithii

Cross-Links

• PubChem: 162993664
• LOTUS: LTS0047852
• wikiData: Q105183916