Harmine C-11

Details

• Internal ID: 2e6ac2e0-aefd-4552-96e5-e667c385453f
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: 7-(111C)methoxy-1-methyl-9H-pyrido[3,4-b]indole
• SMILES (Canonical): CC1=NC=CC2=C1NC3=C2C=CC(=C3)OC
• SMILES (Isomeric): CC1=NC=CC2=C1NC3=C2C=CC(=C3)O[11CH3]
• InChI: InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3/i2-1
• InChI Key: BXNJHAXVSOCGBA-JVVVGQRLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₂N₂O
• Molecular Weight: 211.25 g/mol
• Exact Mass: 211.1063956 g/mol
• Topological Polar Surface Area (TPSA): 37.90 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.03
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• C06QCS6OX3
• UNII-C06QCS6OX3
• 9H-Pyrido(3,4-b)indole, 7-(methoxy-11C)-1-methyl-
• 171882-19-2
• [11C]Harmine
• [11C]HAR
• MOLI001537
• 7-[Methoxy-11C]methyl-9H-[3,4-b]indole

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	+	0.7879	78.79%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8289	82.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9545	95.45%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.5524	55.24%
P-glycoprotein inhibitior	-	0.9379	93.79%
P-glycoprotein substrate	-	0.6866	68.66%
CYP3A4 substrate	-	0.5228	52.28%
CYP2C9 substrate	-	0.7825	78.25%
CYP2D6 substrate	-	0.6664	66.64%
CYP3A4 inhibition	+	0.6929	69.29%
CYP2C9 inhibition	-	0.9481	94.81%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	+	0.9629	96.29%
CYP2C8 inhibition	+	0.5260	52.60%
CYP inhibitory promiscuity	+	0.6307	63.07%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9823	98.23%
Carcinogenicity (trinary)	Non-required	0.4942	49.42%
Eye corrosion	-	0.9899	98.99%
Eye irritation	+	0.7751	77.51%
Skin irritation	-	0.8323	83.23%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	+	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4124	41.24%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.5638	56.38%
skin sensitisation	-	0.9251	92.51%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.8725	87.25%
Acute Oral Toxicity (c)	III	0.6254	62.54%
Estrogen receptor binding	+	0.8701	87.01%
Androgen receptor binding	+	0.8462	84.62%
Thyroid receptor binding	+	0.7327	73.27%
Glucocorticoid receptor binding	+	0.8713	87.13%
Aromatase binding	+	0.8812	88.12%
PPAR gamma	+	0.5826	58.26%
Honey bee toxicity	-	0.9541	95.41%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.8100	81.00%
Fish aquatic toxicity	-	0.7539	75.39%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2111389	O60563	CDK9/cyclin T1	720 nM	IC50	via Super-PRED
CHEMBL5543	Q9Y463	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	28 nM	IC50	via Super-PRED
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	26 nM	IC50	via Super-PRED
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	8.81 nM	IC50	via Super-PRED
CHEMBL4376	Q92630	Dual-specificity tyrosine-phosphorylation regulated kinase 2	120 nM	IC50	via Super-PRED
CHEMBL4575	O43781	Dual-specificity tyrosine-phosphorylation regulated kinase 3	210 nM	IC50	via Super-PRED
CHEMBL1951	P21397	Monoamine oxidase A	5 nM	Ki	via Super-PRED
CHEMBL3923	Q9Y2I1	Nischarin	22 nM	Ki	via Super-PRED
CHEMBL1075163	Q8TF76	Serine/threonine-protein kinase haspin	590 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.48%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.36%	96.09%
CHEMBL1907	P15144	Aminopeptidase N	92.95%	93.31%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.31%	95.56%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	92.12%	96.47%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.33%	93.99%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.05%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.65%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.80%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.61%	97.36%
CHEMBL4208	P20618	Proteasome component C5	85.60%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.73%	96.00%
CHEMBL2424504	P29375	Lysine-specific demethylase 5A	83.90%	99.23%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	83.82%	85.49%
CHEMBL255	P29275	Adenosine A2b receptor	83.77%	98.59%
CHEMBL1781	P11387	DNA topoisomerase I	83.64%	97.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.52%	99.15%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	83.46%	92.67%
CHEMBL2535	P11166	Glucose transporter	82.96%	98.75%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.63%	100.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.41%	93.65%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.15%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	82.07%	94.75%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.77%	86.92%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.57%	96.67%

Plants that contains it

• Elaeagnus angustifolia
• Hippophae rhamnoides
• Passiflora edulis
• Passiflora incarnata
• Peganum harmala
• Polygala tenuifolia
• Tribulus terrestris
• Uncaria rhynchophylla

Cross-Links

• PubChem: 5462124
• NPASS: NPC160125