Dehydroevidiamine

Details

• Internal ID: 1ff9a500-c233-4fd1-b070-23e489778ea1
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
• IUPAC Name: 21-methyl-3,13-diaza-21-azoniapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one
• SMILES (Canonical): C[N+]1=C2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3
• SMILES (Isomeric): C[N+]1=C2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3
• InChI: InChI=1S/C19H15N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9H,10-11H2,1H3/p+1
• InChI Key: VXHNSVKJHXSKKM-UHFFFAOYSA-O
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₆N₃O+
• Molecular Weight: 302.30 g/mol
• Exact Mass: 302.129337142 g/mol
• Topological Polar Surface Area (TPSA): 39.10 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.53
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• CHEMBL81923
• Dehydroevodiamine HCl
• Evodiamine, derivative of
• BDBM50131047
• AKOS040750459
• LS-190115
• S3816
• 14-Methyl-5-oxo-5,7,8,13-tetrahydro-indolo[2'',3'':3,4]pyrido[2,1-b]quinazolin-14-ium

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9695	96.95%
Caco-2	+	0.9314	93.14%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7821	78.21%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.9219	92.19%
OATP1B3 inhibitior	+	0.9416	94.16%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	+	0.6928	69.28%
BSEP inhibitior	+	0.9039	90.39%
P-glycoprotein inhibitior	-	0.6847	68.47%
P-glycoprotein substrate	-	0.7664	76.64%
CYP3A4 substrate	+	0.6008	60.08%
CYP2C9 substrate	-	0.5820	58.20%
CYP2D6 substrate	-	0.8375	83.75%
CYP3A4 inhibition	-	0.7558	75.58%
CYP2C9 inhibition	-	0.8610	86.10%
CYP2C19 inhibition	-	0.9175	91.75%
CYP2D6 inhibition	-	0.8343	83.43%
CYP1A2 inhibition	+	0.8460	84.60%
CYP2C8 inhibition	-	0.8340	83.40%
CYP inhibitory promiscuity	-	0.5886	58.86%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6918	69.18%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9923	99.23%
Skin irritation	-	0.8072	80.72%
Skin corrosion	-	0.9433	94.33%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6933	69.33%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	+	0.7379	73.79%
skin sensitisation	-	0.9031	90.31%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.5198	51.98%
Acute Oral Toxicity (c)	II	0.5379	53.79%
Estrogen receptor binding	+	0.8988	89.88%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6660	66.60%
Glucocorticoid receptor binding	+	0.6429	64.29%
Aromatase binding	+	0.6643	66.43%
PPAR gamma	+	0.5492	54.92%
Honey bee toxicity	-	0.9109	91.09%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	-	0.7712	77.12%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2231	P04798	Cytochrome P450 1A1	18050 nM	IC50	PMID: 12852960
CHEMBL3356	P05177	Cytochrome P450 1A2	5630 nM	IC50	PMID: 12852960
CHEMBL4878	Q16678	Cytochrome P450 1B1	330 nM	IC50	PMID: 12852960
CHEMBL214	P08908	Serotonin 1a (5-HT1a) receptor	36000 nM	Ki	DOI: 10.1021/np960678l

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	98.09%	95.56%
CHEMBL2581	P07339	Cathepsin D	97.48%	98.95%
CHEMBL255	P29275	Adenosine A2b receptor	93.39%	98.59%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.40%	93.40%
CHEMBL3310	Q96DB2	Histone deacetylase 11	88.41%	88.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.85%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.33%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.49%	85.14%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.53%	90.08%
CHEMBL1781	P11387	DNA topoisomerase I	83.04%	97.00%
CHEMBL2535	P11166	Glucose transporter	83.04%	98.75%
CHEMBL1951	P21397	Monoamine oxidase A	82.38%	91.49%

Plants that contains it

• Tetradium ruticarpum

Cross-Links

• PubChem: 156372
• NPASS: NPC117032
• ChEMBL: CHEMBL81923