methyl (1R,12R,19R)-5-hydroxy-12-[(1S)-1-hydroxyethyl]-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,9-tetraene-10-carboxylate

Details

• Internal ID: 5ea9fd14-52cf-4039-b9cf-f5f47edbc598
• Taxonomy: Alkaloids and derivatives > Aspidospermatan-type alkaloids
• IUPAC Name: methyl (1R,12R,19R)-5-hydroxy-12-[(1S)-1-hydroxyethyl]-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,9-tetraene-10-carboxylate
• SMILES (Canonical): CC(C12CCCN3C1C4(CC3)C5=C(C=C(C=C5)O)NC4=C(C2)C(=O)OC)O
• SMILES (Isomeric): C[C@@H]([C@@]12CCCN3[C@@H]1[C@@]4(CC3)C5=C(C=C(C=C5)O)NC4=C(C2)C(=O)OC)O
• InChI: InChI=1S/C21H26N2O4/c1-12(24)20-6-3-8-23-9-7-21(19(20)23)15-5-4-13(25)10-16(15)22-17(21)14(11-20)18(26)27-2/h4-5,10,12,19,22,24-25H,3,6-9,11H2,1-2H3/t12-,19-,20-,21-/m0/s1
• InChI Key: FHMZPCPNSNRDQC-XSGSXHBCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆N₂O₄
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.18925731 g/mol
• Topological Polar Surface Area (TPSA): 82.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.12
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9062	90.62%
Caco-2	+	0.7311	73.11%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7687	76.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8774	87.74%
OATP1B3 inhibitior	+	0.9290	92.90%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6619	66.19%
P-glycoprotein inhibitior	-	0.8443	84.43%
P-glycoprotein substrate	+	0.7924	79.24%
CYP3A4 substrate	+	0.6669	66.69%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.8047	80.47%
CYP3A4 inhibition	-	0.9255	92.55%
CYP2C9 inhibition	-	0.8058	80.58%
CYP2C19 inhibition	-	0.8441	84.41%
CYP2D6 inhibition	-	0.5912	59.12%
CYP1A2 inhibition	-	0.7358	73.58%
CYP2C8 inhibition	+	0.5719	57.19%
CYP inhibitory promiscuity	-	0.7073	70.73%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5792	57.92%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.9834	98.34%
Skin irritation	-	0.7550	75.50%
Skin corrosion	-	0.9295	92.95%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4405	44.05%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.5168	51.68%
skin sensitisation	-	0.8338	83.38%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8188	81.88%
Acute Oral Toxicity (c)	III	0.5649	56.49%
Estrogen receptor binding	+	0.6728	67.28%
Androgen receptor binding	+	0.7202	72.02%
Thyroid receptor binding	-	0.4900	49.00%
Glucocorticoid receptor binding	+	0.7722	77.22%
Aromatase binding	+	0.6830	68.30%
PPAR gamma	+	0.5991	59.91%
Honey bee toxicity	-	0.8566	85.66%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9711	97.11%

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	98.56%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.67%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.77%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.41%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.75%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	95.48%	90.71%
CHEMBL4208	P20618	Proteasome component C5	93.70%	90.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	92.57%	93.03%
CHEMBL2535	P11166	Glucose transporter	89.33%	98.75%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	89.12%	91.03%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	88.44%	85.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.45%	95.89%
CHEMBL240	Q12809	HERG	85.54%	89.76%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.12%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.97%	95.56%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	84.26%	91.65%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.25%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.28%	97.09%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.14%	90.24%
CHEMBL340	P08684	Cytochrome P450 3A4	81.87%	91.19%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.53%	89.62%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.41%	90.93%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.85%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.81%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.79%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.09%	99.23%

Plants that contains it

• Alstonia mairei

Cross-Links

• PubChem: 163044784
• LOTUS: LTS0135951
• wikiData: Q104995352