1-[[(2R,3E,12bS)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]methyl]-2,9-dihydropyrido[3,4-b]indol-7-one

Details

• Internal ID: 88533504-e089-4050-a448-2648188a5d5b
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: 1-[[(2R,3E,12bS)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]methyl]-2,9-dihydropyrido[3,4-b]indol-7-one
• SMILES (Canonical): CC=C1CN2CCC3=C(C2CC1CC4=C5C(=C6C=CC(=O)C=C6N5)C=CN4)NC7=CC=CC=C37
• SMILES (Isomeric): C/C=C\1/CN2CCC3=C([C@@H]2C[C@@H]1CC4=C5C(=C6C=CC(=O)C=C6N5)C=CN4)NC7=CC=CC=C37
• InChI: InChI=1S/C29H28N4O/c1-2-17-16-33-12-10-23-20-5-3-4-6-24(20)31-29(23)27(33)14-18(17)13-26-28-22(9-11-30-26)21-8-7-19(34)15-25(21)32-28/h2-9,11,15,18,27,30-32H,10,12-14,16H2,1H3/b17-2-/t18-,27-/m0/s1
• InChI Key: KQQKDNVPESYGBB-JKCZZUPASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₂₈N₄O
• Molecular Weight: 448.60 g/mol
• Exact Mass: 448.22631153 g/mol
• Topological Polar Surface Area (TPSA): 60.20 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 5.60
• H-Bond Acceptor: 2
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• NSC703771
• NSC-703771

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9924	99.24%
Caco-2	-	0.6356	63.56%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6028	60.28%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8327	83.27%
OATP1B3 inhibitior	+	0.9377	93.77%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.9852	98.52%
P-glycoprotein inhibitior	+	0.9789	97.89%
P-glycoprotein substrate	+	0.5443	54.43%
CYP3A4 substrate	+	0.7045	70.45%
CYP2C9 substrate	-	0.5939	59.39%
CYP2D6 substrate	-	0.6661	66.61%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8208	82.08%
CYP2C19 inhibition	-	0.8161	81.61%
CYP2D6 inhibition	+	0.6575	65.75%
CYP1A2 inhibition	+	0.6030	60.30%
CYP2C8 inhibition	+	0.6832	68.32%
CYP inhibitory promiscuity	+	0.5982	59.82%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6508	65.08%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9717	97.17%
Skin irritation	-	0.7274	72.74%
Skin corrosion	-	0.9201	92.01%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8927	89.27%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8512	85.12%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5483	54.83%
Acute Oral Toxicity (c)	III	0.4992	49.92%
Estrogen receptor binding	+	0.8047	80.47%
Androgen receptor binding	+	0.8212	82.12%
Thyroid receptor binding	+	0.7482	74.82%
Glucocorticoid receptor binding	+	0.7746	77.46%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6180	61.80%
Honey bee toxicity	-	0.7912	79.12%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9335	93.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.34%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.85%	95.56%
CHEMBL2581	P07339	Cathepsin D	97.46%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.96%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.85%	93.40%
CHEMBL255	P29275	Adenosine A2b receptor	95.28%	98.59%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.90%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.89%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	93.24%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.77%	89.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	90.09%	91.71%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.21%	93.99%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.45%	97.09%
CHEMBL217	P14416	Dopamine D2 receptor	87.43%	95.62%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	87.37%	90.71%
CHEMBL2535	P11166	Glucose transporter	86.21%	98.75%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	86.08%	85.00%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	85.44%	81.14%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	85.24%	96.42%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.49%	95.83%
CHEMBL240	Q12809	HERG	83.42%	89.76%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	82.93%	82.38%
CHEMBL2803	P43403	Tyrosine-protein kinase ZAP-70	82.88%	82.50%
CHEMBL228	P31645	Serotonin transporter	82.81%	95.51%
CHEMBL4302	P08183	P-glycoprotein 1	81.94%	92.98%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.21%	90.24%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	80.68%	92.67%

Plants that contains it

• Strychnos usambarensis

Cross-Links

• PubChem: 54611444
• NPASS: NPC39530