Escholtzine

Details

• Internal ID: 9be779ba-56df-4bc3-b66e-54acc01efb18
• Taxonomy: Alkaloids and derivatives > Pavine alkaloids
• IUPAC Name: (1S,12S)-23-methyl-5,7,16,18-tetraoxa-23-azahexacyclo[10.10.1.02,10.04,8.013,21.015,19]tricosa-2,4(8),9,13,15(19),20-hexaene
• SMILES (Canonical): CN1C2CC3=CC4=C(C=C3C1CC5=CC6=C(C=C25)OCO6)OCO4
• SMILES (Isomeric): CN1[C@H]2CC3=CC4=C(C=C3[C@@H]1CC5=CC6=C(C=C25)OCO6)OCO4
• InChI: InChI=1S/C19H17NO4/c1-20-14-2-10-4-16-18(23-8-21-16)6-12(10)15(20)3-11-5-17-19(7-13(11)14)24-9-22-17/h4-7,14-15H,2-3,8-9H2,1H3/t14-,15-/m0/s1
• InChI Key: PGINMPJZCWDQNT-GJZGRUSLSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₇NO₄
• Molecular Weight: 323.30 g/mol
• Exact Mass: 323.11575802 g/mol
• Topological Polar Surface Area (TPSA): 40.20 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.97
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Crychine
• Escholzine
• 4040-75-9
• CHEMBL481839
• (1S,12S)-23-methyl-5,7,16,18-tetraoxa-23-azahexacyclo[10.10.1.02,10.04,8.013,21.015,19]tricosa-2,4(8),9,13,15(19),20-hexaene
• D06DSX
• DTXSID70904965
• BDBM50259677

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9829	98.29%
Caco-2	+	0.8451	84.51%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Lysosomes	0.4239	42.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9476	94.76%
OATP1B3 inhibitior	+	0.9567	95.67%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.8735	87.35%
P-glycoprotein inhibitior	-	0.5690	56.90%
P-glycoprotein substrate	-	0.9188	91.88%
CYP3A4 substrate	-	0.6186	61.86%
CYP2C9 substrate	-	0.5820	58.20%
CYP2D6 substrate	+	0.6456	64.56%
CYP3A4 inhibition	+	0.6424	64.24%
CYP2C9 inhibition	-	0.8764	87.64%
CYP2C19 inhibition	+	0.7046	70.46%
CYP2D6 inhibition	+	0.7938	79.38%
CYP1A2 inhibition	+	0.8458	84.58%
CYP2C8 inhibition	-	0.9901	99.01%
CYP inhibitory promiscuity	+	0.6960	69.60%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5530	55.30%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.8697	86.97%
Skin irritation	-	0.7140	71.40%
Skin corrosion	-	0.9337	93.37%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6777	67.77%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.8352	83.52%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.4507	45.07%
Acute Oral Toxicity (c)	III	0.7296	72.96%
Estrogen receptor binding	+	0.8163	81.63%
Androgen receptor binding	-	0.5206	52.06%
Thyroid receptor binding	+	0.6171	61.71%
Glucocorticoid receptor binding	+	0.7590	75.90%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7902	79.02%
Honey bee toxicity	-	0.8849	88.49%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.8171	81.71%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	13400 nM	IC50	PMID: 16562853
CHEMBL214	P08908	Serotonin 1a (5-HT1a) receptor	6000 nM	Ki	PMID: 16562853

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.84%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.10%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.71%	96.77%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	89.31%	80.96%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.62%	89.62%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.89%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.00%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.70%	94.80%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.67%	90.71%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.87%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.79%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.73%	95.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.22%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.06%	95.89%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.57%	86.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.40%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.91%	86.33%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.80%	90.24%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.10%	95.89%

Plants that contains it

• Andira surinamensis
• Aralia hispida
• Baeckea frutescens
• Balanophora polyandra
• Boeberastrum anthemidifolium
• Chenopodiastrum murale
• Chenopodium quinoa
• Citrus medica
• Coprosma foetidissima
• Cryptocarya chinensis
• Davidsonia pruriens
• Echinochloa crus-galli
• Eriocephalus kingesii
• Eschscholzia californica
• Geranium collinum
• Girgensohnia oppositiflora
• Harpullia cupanioides
• Isodon eriocalyx
• Lilium pomponium
• Lychnophora pinaster
• Marrubium parviflorum
• Microglossa pyrifolia
• Parthenium confertum
• Polygonatum orientale
• Psathyrotes ramosissima
• Scleropyrum pentandrum
• Selliguea hastata
• Trifolium diffusum
• Veronica stricta
• Youngia japonica
• Zanthoxylum acuminatum subsp. juniperinum

Cross-Links

• PubChem: 12304178
• NPASS: NPC210148
• ChEMBL: CHEMBL481839
• LOTUS: LTS0051647
• wikiData: Q81983388