Koumine

Details

• Internal ID: ce350831-b25b-49c8-ab9a-7d9c73ce7700
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indoles > 3-alkylindoles
• IUPAC Name: (1S,10S,12S,15S,16R,17S)-15-ethenyl-13-methyl-19-oxa-3,13-diazahexacyclo[14.3.1.02,10.04,9.010,15.012,17]icosa-2,4,6,8-tetraene
• SMILES (Canonical): CN1CC2(C3CC4C5=NC6=CC=CC=C6C52CC1C3CO4)C=C
• SMILES (Isomeric): CN1C[C@]2([C@@H]3C[C@H]4C5=NC6=CC=CC=C6[C@@]52C[C@H]1[C@H]3CO4)C=C
• InChI: InChI=1S/C20H22N2O/c1-3-19-11-22(2)16-9-20(19)13-6-4-5-7-15(13)21-18(20)17-8-14(19)12(16)10-23-17/h3-7,12,14,16-17H,1,8-11H2,2H3/t12-,14+,16-,17-,19-,20-/m0/s1
• InChI Key: VTLYEMHGPMGUOT-XMHJOAAQSA-N
• Popularity: 61 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂N₂O
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.173213330 g/mol
• Topological Polar Surface Area (TPSA): 24.80 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.94
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 1358-76-5
• CHEMBL522743
• AKOS040758841

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9560	95.60%
Caco-2	+	0.7212	72.12%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Plasma membrane	0.3754	37.54%
OATP2B1 inhibitior	-	0.8618	86.18%
OATP1B1 inhibitior	+	0.9113	91.13%
OATP1B3 inhibitior	+	0.9416	94.16%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.5677	56.77%
P-glycoprotein inhibitior	-	0.8720	87.20%
P-glycoprotein substrate	+	0.5283	52.83%
CYP3A4 substrate	+	0.6602	66.02%
CYP2C9 substrate	-	0.5799	57.99%
CYP2D6 substrate	+	0.4846	48.46%
CYP3A4 inhibition	-	0.8634	86.34%
CYP2C9 inhibition	-	0.8483	84.83%
CYP2C19 inhibition	-	0.6378	63.78%
CYP2D6 inhibition	-	0.6958	69.58%
CYP1A2 inhibition	-	0.6970	69.70%
CYP2C8 inhibition	+	0.4599	45.99%
CYP inhibitory promiscuity	-	0.7033	70.33%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.6090	60.90%
Eye corrosion	-	0.9804	98.04%
Eye irritation	-	0.9856	98.56%
Skin irritation	-	0.7569	75.69%
Skin corrosion	-	0.8474	84.74%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8956	89.56%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.5744	57.44%
skin sensitisation	-	0.7848	78.48%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7055	70.55%
Acute Oral Toxicity (c)	III	0.6020	60.20%
Estrogen receptor binding	+	0.6940	69.40%
Androgen receptor binding	+	0.7144	71.44%
Thyroid receptor binding	+	0.6854	68.54%
Glucocorticoid receptor binding	+	0.6362	63.62%
Aromatase binding	-	0.5925	59.25%
PPAR gamma	-	0.6886	68.86%
Honey bee toxicity	-	0.7567	75.67%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.8793	87.93%

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	95.04%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.04%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.98%	97.25%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	88.77%	100.00%
CHEMBL4208	P20618	Proteasome component C5	87.85%	90.00%
CHEMBL1951	P21397	Monoamine oxidase A	86.97%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.60%	86.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.59%	82.69%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.00%	93.40%
CHEMBL5805	Q9NR97	Toll-like receptor 8	82.14%	96.25%

Plants that contains it

• Gelsemium elegans

Cross-Links

• PubChem: 44583834
• NPASS: NPC116519