(2R,3R,12bS)-3-ethyl-11-[(2S)-1-methylpyrrolidin-2-yl]-2-[[(1S)-2-methyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-1-yl]methyl]-1,2,3,4,6,7,7a,12,12a,12b-decahydroindolo[2,3-a]quinolizin-10-ol

Details

• Internal ID: f6d7c958-7292-4763-95ce-ae48dec4f95f
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: (2R,3R,12bS)-3-ethyl-11-[(2S)-1-methylpyrrolidin-2-yl]-2-[[(1S)-2-methyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-1-yl]methyl]-1,2,3,4,6,7,7a,12,12a,12b-decahydroindolo[2,3-a]quinolizin-10-ol
• SMILES (Canonical): CCC1CN2CCC3C(C2CC1CC4C5=C(CCN4C)C6=CC=CC=C6N5)NC7=C3C=CC(=C7C8CCCN8C)O
• SMILES (Isomeric): CC[C@H]1CN2CCC3C([C@@H]2C[C@@H]1C[C@H]4C5=C(CCN4C)C6=CC=CC=C6N5)NC7=C3C=CC(=C7[C@@H]8CCCN8C)O
• InChI: InChI=1S/C35H47N5O/c1-4-21-20-40-17-14-26-24-11-12-31(41)32(28-10-7-15-38(28)2)35(24)37-34(26)30(40)19-22(21)18-29-33-25(13-16-39(29)3)23-8-5-6-9-27(23)36-33/h5-6,8-9,11-12,21-22,26,28-30,34,36-37,41H,4,7,10,13-20H2,1-3H3/t21-,22-,26?,28-,29-,30-,34?/m0/s1
• InChI Key: MHIOYLXTHAIJLU-FVHQJPTNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₇N₅O
• Molecular Weight: 553.80 g/mol
• Exact Mass: 553.37806114 g/mol
• Topological Polar Surface Area (TPSA): 57.80 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 6.26
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• SCHEMBL31237461

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9751	97.51%
Caco-2	-	0.6961	69.61%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5113	51.13%
OATP2B1 inhibitior	-	0.7136	71.36%
OATP1B1 inhibitior	+	0.8280	82.80%
OATP1B3 inhibitior	+	0.9254	92.54%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.9848	98.48%
P-glycoprotein inhibitior	+	0.8417	84.17%
P-glycoprotein substrate	+	0.8248	82.48%
CYP3A4 substrate	+	0.7400	74.00%
CYP2C9 substrate	-	0.7928	79.28%
CYP2D6 substrate	+	0.6212	62.12%
CYP3A4 inhibition	-	0.7179	71.79%
CYP2C9 inhibition	-	0.8398	83.98%
CYP2C19 inhibition	-	0.7584	75.84%
CYP2D6 inhibition	+	0.5331	53.31%
CYP1A2 inhibition	-	0.5344	53.44%
CYP2C8 inhibition	+	0.6592	65.92%
CYP inhibitory promiscuity	+	0.6518	65.18%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6865	68.65%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.9614	96.14%
Skin irritation	-	0.7665	76.65%
Skin corrosion	-	0.9221	92.21%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9318	93.18%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8791	87.91%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.7133	71.33%
Acute Oral Toxicity (c)	III	0.6200	62.00%
Estrogen receptor binding	+	0.7992	79.92%
Androgen receptor binding	+	0.8059	80.59%
Thyroid receptor binding	+	0.5224	52.24%
Glucocorticoid receptor binding	+	0.6223	62.23%
Aromatase binding	+	0.5843	58.43%
PPAR gamma	+	0.6554	65.54%
Honey bee toxicity	-	0.8028	80.28%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	0.9373	93.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	99.96%	89.76%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.54%	96.09%
CHEMBL217	P14416	Dopamine D2 receptor	97.20%	95.62%
CHEMBL2581	P07339	Cathepsin D	97.05%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.87%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.27%	97.25%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	96.25%	91.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.89%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.77%	97.09%
CHEMBL233	P35372	Mu opioid receptor	93.61%	97.93%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.10%	93.99%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	92.00%	96.42%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	91.72%	97.50%
CHEMBL5103	Q969S8	Histone deacetylase 10	90.77%	90.08%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	90.07%	90.71%
CHEMBL228	P31645	Serotonin transporter	89.83%	95.51%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.53%	95.89%
CHEMBL1902	P62942	FK506-binding protein 1A	88.60%	97.05%
CHEMBL238	Q01959	Dopamine transporter	87.83%	95.88%
CHEMBL3310	Q96DB2	Histone deacetylase 11	87.82%	88.56%
CHEMBL206	P03372	Estrogen receptor alpha	87.01%	97.64%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.61%	94.45%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	85.74%	85.83%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.61%	85.14%
CHEMBL2535	P11166	Glucose transporter	85.29%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.23%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.11%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	85.01%	91.49%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.74%	93.03%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.90%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.48%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.24%	89.62%
CHEMBL5203	P33316	dUTP pyrophosphatase	83.05%	99.18%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	82.83%	98.46%
CHEMBL1808	P12821	Angiotensin-converting enzyme	81.11%	93.39%

Plants that contains it

• Strychnos usambarensis
• Strychnos usambarensis

Cross-Links

• PubChem: 44559861
• NPASS: NPC183407
• ChEMBL: CHEMBL496076
• LOTUS: LTS0246228
• wikiData: Q105163828