(-)-Argemonine

Details

• Internal ID: 13acabcd-d67d-42dd-8d3e-7f71011c6464
• Taxonomy: Alkaloids and derivatives > Pavine alkaloids
• IUPAC Name: (1S,9S)-4,5,12,13-tetramethoxy-17-methyl-17-azatetracyclo[7.7.1.02,7.010,15]heptadeca-2,4,6,10,12,14-hexaene
• SMILES (Canonical): CN1C2CC3=CC(=C(C=C3C1CC4=CC(=C(C=C24)OC)OC)OC)OC
• SMILES (Isomeric): CN1[C@H]2CC3=CC(=C(C=C3[C@@H]1CC4=CC(=C(C=C24)OC)OC)OC)OC
• InChI: InChI=1S/C21H25NO4/c1-22-16-6-12-8-18(23-2)20(25-4)10-14(12)17(22)7-13-9-19(24-3)21(26-5)11-15(13)16/h8-11,16-17H,6-7H2,1-5H3/t16-,17-/m0/s1
• InChI Key: QEOWCPFWLCIQSL-IRXDYDNUSA-N
• Popularity: 32 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.40 g/mol
• Exact Mass: 355.17835828 g/mol
• Topological Polar Surface Area (TPSA): 40.20 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.55
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• Argemonine
• 6901-16-2
• benzene-1,2,4-tricarboxylic acid- 2-ethylhexan-1-ol(1:1)
• Argemonine (8CI)
• C09341
• CN1C2Cc3cc(OC)c(OC)cc3C1Cc4cc(OC)c(OC)cc24
• CHEBI:80
• DTXSID201317226
• Q27105226
• (1S,9S)-4,5,12,13-tetramethoxy-17-methyl-17-azatetracyclo[7.7.1.02,7.010,15]heptadeca-2,4,6,10,12,14-hexaene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9830	98.30%
Caco-2	+	0.9045	90.45%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Nucleus	0.4166	41.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9390	93.90%
OATP1B3 inhibitior	+	0.9663	96.63%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.8199	81.99%
P-glycoprotein inhibitior	+	0.7956	79.56%
P-glycoprotein substrate	-	0.6515	65.15%
CYP3A4 substrate	-	0.5395	53.95%
CYP2C9 substrate	+	0.7753	77.53%
CYP2D6 substrate	+	0.8760	87.60%
CYP3A4 inhibition	-	0.5541	55.41%
CYP2C9 inhibition	-	0.8947	89.47%
CYP2C19 inhibition	-	0.6543	65.43%
CYP2D6 inhibition	+	0.6817	68.17%
CYP1A2 inhibition	+	0.6138	61.38%
CYP2C8 inhibition	-	0.9693	96.93%
CYP inhibitory promiscuity	-	0.6379	63.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9710	97.10%
Carcinogenicity (trinary)	Non-required	0.5812	58.12%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.8428	84.28%
Skin irritation	-	0.7763	77.63%
Skin corrosion	-	0.9521	95.21%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7538	75.38%
Micronuclear	+	0.6059	60.59%
Hepatotoxicity	+	0.5159	51.59%
skin sensitisation	-	0.9265	92.65%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6872	68.72%
Acute Oral Toxicity (c)	III	0.6798	67.98%
Estrogen receptor binding	+	0.8096	80.96%
Androgen receptor binding	-	0.6322	63.22%
Thyroid receptor binding	+	0.7458	74.58%
Glucocorticoid receptor binding	+	0.7622	76.22%
Aromatase binding	-	0.7319	73.19%
PPAR gamma	+	0.5981	59.81%
Honey bee toxicity	-	0.8395	83.95%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	+	0.8416	84.16%

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	98.49%	96.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	94.32%	89.62%
CHEMBL2581	P07339	Cathepsin D	93.56%	98.95%
CHEMBL217	P14416	Dopamine D2 receptor	89.09%	95.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.67%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.49%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.27%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.05%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.96%	95.89%
CHEMBL2535	P11166	Glucose transporter	83.22%	98.75%
CHEMBL1902	P62942	FK506-binding protein 1A	82.78%	97.05%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	80.82%	96.86%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.79%	99.17%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.46%	93.99%

Plants that contains it

• Andira surinamensis
• Aralia hispida
• Argemone mexicana
• Argemone polyanthemos
• Baeckea frutescens
• Balanophora polyandra
• Berberis microphylla
• Boeberastrum anthemidifolium
• Chenopodiastrum murale
• Chenopodium quinoa
• Citrus medica
• Coleonema pulchellum
• Coprosma foetidissima
• Cryptocarya chinensis
• Cyclea atjehensis
• Davidsonia pruriens
• Echinochloa crus-galli
• Eriocephalus kingesii
• 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
• Tamarix chinensis
• Thalictrum minus
• Thalictrum simplex
• Trifolium diffusum
• Veronica stricta
• Youngia japonica
• Zanthoxylum acuminatum subsp. juniperinum

Cross-Links

• PubChem: 442168
• NPASS: NPC65196
• LOTUS: LTS0164075
• wikiData: Q27105226