4-(4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl)-7-methoxy-2,3,4,12-tetrahydro-1H-indolo[2,3-a]quinolizin-5-ium

Details

• Internal ID: 646de0f7-73a3-484b-b10c-c66dc9d9569c
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: 4-(4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl)-7-methoxy-2,3,4,12-tetrahydro-1H-indolo[2,3-a]quinolizin-5-ium
• SMILES (Canonical): COC1=CC=CC2=C1NC3=C2C(=CN=C3C4CCCC5=[N+]4C=C(C6=C5NC7=CC=CC=C76)OC)OC
• SMILES (Isomeric): COC1=CC=CC2=C1NC3=C2C(=CN=C3C4CCCC5=[N+]4C=C(C6=C5NC7=CC=CC=C76)OC)OC
• InChI: InChI=1S/C29H26N4O3/c1-34-21-13-6-9-17-25-22(35-2)14-30-28(29(25)32-26(17)21)20-12-7-11-19-27-24(23(36-3)15-33(19)20)16-8-4-5-10-18(16)31-27/h4-6,8-10,13-15,20H,7,11-12H2,1-3H3,(H,30,32)/p+1
• InChI Key: NQZOCXBXUNDIIB-UHFFFAOYSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₂₇N₄O₃+
• Molecular Weight: 479.50 g/mol
• Exact Mass: 479.20831574 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.59
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9526	95.26%
Caco-2	-	0.6796	67.96%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.9268	92.68%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.9114	91.14%
OATP1B3 inhibitior	+	0.9311	93.11%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.9871	98.71%
P-glycoprotein inhibitior	+	0.9164	91.64%
P-glycoprotein substrate	+	0.6136	61.36%
CYP3A4 substrate	+	0.7039	70.39%
CYP2C9 substrate	-	0.6433	64.33%
CYP2D6 substrate	+	0.3618	36.18%
CYP3A4 inhibition	+	0.5666	56.66%
CYP2C9 inhibition	-	0.7652	76.52%
CYP2C19 inhibition	-	0.6240	62.40%
CYP2D6 inhibition	+	0.5321	53.21%
CYP1A2 inhibition	+	0.5982	59.82%
CYP2C8 inhibition	+	0.9169	91.69%
CYP inhibitory promiscuity	+	0.8833	88.33%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5977	59.77%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9628	96.28%
Skin irritation	-	0.8039	80.39%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	+	0.5463	54.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.8848	88.48%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.9049	90.49%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.7169	71.69%
Acute Oral Toxicity (c)	III	0.5225	52.25%
Estrogen receptor binding	+	0.8619	86.19%
Androgen receptor binding	+	0.7581	75.81%
Thyroid receptor binding	+	0.8185	81.85%
Glucocorticoid receptor binding	+	0.9096	90.96%
Aromatase binding	+	0.6398	63.98%
PPAR gamma	+	0.7852	78.52%
Honey bee toxicity	-	0.8353	83.53%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	-	0.4827	48.27%

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	97.30%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.95%	95.56%
CHEMBL4302	P08183	P-glycoprotein 1	94.42%	92.98%
CHEMBL2535	P11166	Glucose transporter	94.39%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.33%	94.00%
CHEMBL213	P08588	Beta-1 adrenergic receptor	94.04%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.79%	93.99%
CHEMBL2581	P07339	Cathepsin D	92.83%	98.95%
CHEMBL5203	P33316	dUTP pyrophosphatase	91.15%	99.18%
CHEMBL1937	Q92769	Histone deacetylase 2	90.14%	94.75%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	89.37%	85.49%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	89.15%	89.44%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.05%	91.11%
CHEMBL3524	P56524	Histone deacetylase 4	88.92%	92.97%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.68%	99.23%
CHEMBL3310	Q96DB2	Histone deacetylase 11	88.56%	88.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.47%	97.09%
CHEMBL5747	Q92793	CREB-binding protein	87.64%	95.12%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.03%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.95%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.63%	96.00%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	85.82%	95.48%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	84.91%	92.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.40%	89.00%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	84.33%	97.64%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.76%	90.08%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	82.22%	96.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.10%	91.71%
CHEMBL1907	P15144	Aminopeptidase N	81.96%	93.31%
CHEMBL1951	P21397	Monoamine oxidase A	81.68%	91.49%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	81.65%	94.03%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	81.55%	97.23%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.27%	96.39%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.82%	92.94%

Plants that contains it

• Picrasma quassioides

Cross-Links

• PubChem: 21637829
• LOTUS: LTS0092640
• wikiData: Q105184212