(1S,3R)-1-(4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl)-3-methoxy-3-(9H-pyrido[3,4-b]indol-1-yl)propan-1-ol

Details

• Internal ID: 1d5ddea0-f524-47c0-b251-d880ece2d4e7
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: (1S,3R)-1-(4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl)-3-methoxy-3-(9H-pyrido[3,4-b]indol-1-yl)propan-1-ol
• SMILES (Canonical): COC1=CC=CC2=C1NC3=C2C(=CN=C3C(CC(C4=NC=CC5=C4NC6=CC=CC=C56)OC)O)OC
• SMILES (Isomeric): COC1=CC=CC2=C1NC3=C2C(=CN=C3[C@H](C[C@H](C4=NC=CC5=C4NC6=CC=CC=C56)OC)O)OC
• InChI: InChI=1S/C28H26N4O4/c1-34-20-10-6-8-17-23-22(36-3)14-30-26(28(23)32-24(17)20)19(33)13-21(35-2)27-25-16(11-12-29-27)15-7-4-5-9-18(15)31-25/h4-12,14,19,21,31-33H,13H2,1-3H3/t19-,21+/m0/s1
• InChI Key: XVEJXALIVXUAGW-PZJWPPBQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₆N₄O₄
• Molecular Weight: 482.50 g/mol
• Exact Mass: 482.19540532 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 5.57
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9560	95.60%
Caco-2	-	0.6427	64.27%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5486	54.86%
OATP2B1 inhibitior	-	0.8604	86.04%
OATP1B1 inhibitior	+	0.8989	89.89%
OATP1B3 inhibitior	+	0.9382	93.82%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9576	95.76%
P-glycoprotein inhibitior	+	0.8181	81.81%
P-glycoprotein substrate	+	0.7051	70.51%
CYP3A4 substrate	+	0.6720	67.20%
CYP2C9 substrate	-	0.8030	80.30%
CYP2D6 substrate	+	0.4346	43.46%
CYP3A4 inhibition	-	0.6625	66.25%
CYP2C9 inhibition	-	0.9085	90.85%
CYP2C19 inhibition	-	0.7591	75.91%
CYP2D6 inhibition	-	0.6805	68.05%
CYP1A2 inhibition	-	0.5808	58.08%
CYP2C8 inhibition	+	0.8397	83.97%
CYP inhibitory promiscuity	+	0.5567	55.67%
UGT catelyzed	-	0.5841	58.41%
Carcinogenicity (binary)	-	0.9523	95.23%
Carcinogenicity (trinary)	Non-required	0.5437	54.37%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9185	91.85%
Skin irritation	-	0.8279	82.79%
Skin corrosion	-	0.9412	94.12%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7944	79.44%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.9009	90.09%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.5983	59.83%
Acute Oral Toxicity (c)	III	0.6454	64.54%
Estrogen receptor binding	+	0.8231	82.31%
Androgen receptor binding	+	0.8120	81.20%
Thyroid receptor binding	+	0.7733	77.33%
Glucocorticoid receptor binding	+	0.8170	81.70%
Aromatase binding	+	0.6309	63.09%
PPAR gamma	+	0.7230	72.30%
Honey bee toxicity	-	0.7718	77.18%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	-	0.8246	82.46%

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	99.11%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.73%	85.14%
CHEMBL213	P08588	Beta-1 adrenergic receptor	95.27%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.64%	98.95%
CHEMBL1907	P15144	Aminopeptidase N	93.99%	93.31%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.90%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.25%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.15%	93.99%
CHEMBL2535	P11166	Glucose transporter	90.25%	98.75%
CHEMBL5747	Q92793	CREB-binding protein	88.03%	95.12%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.97%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.93%	99.17%
CHEMBL255	P29275	Adenosine A2b receptor	86.39%	98.59%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.27%	96.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.96%	96.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.91%	89.00%
CHEMBL2885	P07451	Carbonic anhydrase III	84.51%	87.45%
CHEMBL3310	Q96DB2	Histone deacetylase 11	83.37%	88.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.00%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	82.97%	94.75%
CHEMBL1781	P11387	DNA topoisomerase I	82.87%	97.00%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	82.56%	85.49%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	81.66%	89.44%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.54%	100.00%

Plants that contains it

• Picrasma quassioides

Cross-Links

• PubChem: 162958599
• LOTUS: LTS0151972
• wikiData: Q105342807