(2S,13S,15R,16R,19R,20R)-19-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.02,16.04,12.05,10.015,20]henicosa-4(12),5,7,9-tetraen-19-ol

Details

• Internal ID: d3b706c8-dc85-405e-b922-3e934a8ff48f
• Taxonomy: Alkaloids and derivatives > Macroline alkaloids
• IUPAC Name: (2S,13S,15R,16R,19R,20R)-19-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.02,16.04,12.05,10.015,20]henicosa-4(12),5,7,9-tetraen-19-ol
• SMILES (Canonical): CC1(C2CN3C4CC2C(C3CC5=C4NC6=CC=CC=C56)CO1)O
• SMILES (Isomeric): C[C@@]1([C@H]2CN3[C@H]4C[C@@H]2[C@H]([C@@H]3CC5=C4NC6=CC=CC=C56)CO1)O
• InChI: InChI=1S/C19H22N2O2/c1-19(22)14-8-21-16-7-12-10-4-2-3-5-15(10)20-18(12)17(21)6-11(14)13(16)9-23-19/h2-5,11,13-14,16-17,20,22H,6-9H2,1H3/t11-,13-,14+,16+,17+,19-/m1/s1
• InChI Key: VDZMDAYPDAXEMB-BVQNVKBFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂N₂O₂
• Molecular Weight: 310.40 g/mol
• Exact Mass: 310.168127949 g/mol
• Topological Polar Surface Area (TPSA): 48.50 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.44
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9646	96.46%
Caco-2	+	0.7562	75.62%
Blood Brain Barrier	+	0.8129	81.29%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Lysosomes	0.6027	60.27%
OATP2B1 inhibitior	-	0.8617	86.17%
OATP1B1 inhibitior	+	0.8845	88.45%
OATP1B3 inhibitior	+	0.9391	93.91%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.7562	75.62%
P-glycoprotein inhibitior	-	0.9246	92.46%
P-glycoprotein substrate	+	0.5097	50.97%
CYP3A4 substrate	+	0.6915	69.15%
CYP2C9 substrate	-	0.8093	80.93%
CYP2D6 substrate	+	0.4070	40.70%
CYP3A4 inhibition	-	0.7408	74.08%
CYP2C9 inhibition	-	0.8958	89.58%
CYP2C19 inhibition	-	0.7414	74.14%
CYP2D6 inhibition	-	0.5773	57.73%
CYP1A2 inhibition	-	0.5939	59.39%
CYP2C8 inhibition	+	0.4684	46.84%
CYP inhibitory promiscuity	-	0.6478	64.78%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6315	63.15%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9871	98.71%
Skin irritation	-	0.7801	78.01%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	+	0.5446	54.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7719	77.19%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.5466	54.66%
skin sensitisation	-	0.8678	86.78%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.5950	59.50%
Acute Oral Toxicity (c)	III	0.4529	45.29%
Estrogen receptor binding	+	0.7182	71.82%
Androgen receptor binding	+	0.7000	70.00%
Thyroid receptor binding	+	0.6712	67.12%
Glucocorticoid receptor binding	-	0.6077	60.77%
Aromatase binding	-	0.4900	49.00%
PPAR gamma	+	0.5223	52.23%
Honey bee toxicity	-	0.8405	84.05%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.8237	82.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.27%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.08%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	93.19%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.28%	97.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.84%	94.62%
CHEMBL3310	Q96DB2	Histone deacetylase 11	91.63%	88.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.51%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.26%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.47%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.41%	98.95%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	88.86%	94.08%
CHEMBL240	Q12809	HERG	86.41%	89.76%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.31%	85.14%
CHEMBL1902	P62942	FK506-binding protein 1A	83.74%	97.05%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	83.74%	96.39%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.18%	82.69%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	82.76%	85.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.80%	100.00%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	81.46%	95.48%
CHEMBL5028	O14672	ADAM10	81.09%	97.50%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.61%	94.23%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.02%	85.11%

Plants that contains it

• Strychnos trinervis

Cross-Links

• PubChem: 101168507
• LOTUS: LTS0116115
• wikiData: Q105284456