Harmalan

Details

• Internal ID: 7953e174-5945-4d2b-b422-fd11577ebff2
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: 1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
• SMILES (Canonical): CC1=NCCC2=C1NC3=CC=CC=C23
• SMILES (Isomeric): CC1=NCCC2=C1NC3=CC=CC=C23
• InChI: InChI=1S/C12H12N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-5,14H,6-7H2,1H3
• InChI Key: CWOYLIJQLSNRRN-UHFFFAOYSA-N
• Popularity: 36 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₂N₂
• Molecular Weight: 184.24 g/mol
• Exact Mass: 184.100048391 g/mol
• Topological Polar Surface Area (TPSA): 28.20 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.53
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 525-41-7
• 1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole
• 1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
• 1-Methyl-4,9-dihydro-3H-beta-carboline
• 1-Methyl-3,4-dihydro-beta-carboline
• CHEMBL295234
• Dihydroharman
• harman e
• 1-methyl-3H,4H,9H-pyrido[3,4-b]indole
• 3,4-dihydroharman
• Oprea1_558389
• MLS001048999
• SCHEMBL141724
• SCHEMBL4986696
• DTXSID80966938
• BJRYQXFFBCGJRM-UHFFFAOYSA-N
• CHEBI:168077
• REGID_for_CID_5316718
• HMS2270L19
• HMS3561H09
• BDBM50136493
• AKOS006282713
• HY-W194842
• NCGC00245167-01
• NCGC00245167-02
• PD119393
• SMR000387013
• 1-Methyl-3,4-dihydro-2H-.beta.-carboline
• CS-0257555
• 3,4-Dihydro-1-methyl-2H-Pyrido[3,4-b]indole
• 4,9-Dihydro-1-methyl-3H-Pyrido(3,4-b)indole
• EN300-6738068
• 2H-Pyrido[3,4-b]indole, 3,4-dihydro-1-methyl-
• 3H-Pyrido(3,4-b)indole, 4,9-dihydro-1-methyl-
• A827586
• 4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indole, 9CI
• Z1198723409

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9946	99.46%
Caco-2	-	0.8339	83.39%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Lysosomes	0.4247	42.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9499	94.99%
OATP1B3 inhibitior	+	0.9468	94.68%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.7000	70.00%
BSEP inhibitior	-	0.6406	64.06%
P-glycoprotein inhibitior	-	0.9797	97.97%
P-glycoprotein substrate	-	0.9176	91.76%
CYP3A4 substrate	+	0.5356	53.56%
CYP2C9 substrate	+	0.5969	59.69%
CYP2D6 substrate	-	0.8062	80.62%
CYP3A4 inhibition	+	0.5776	57.76%
CYP2C9 inhibition	-	0.9427	94.27%
CYP2C19 inhibition	-	0.8060	80.60%
CYP2D6 inhibition	-	0.5587	55.87%
CYP1A2 inhibition	+	0.8072	80.72%
CYP2C8 inhibition	-	0.7277	72.77%
CYP inhibitory promiscuity	-	0.7678	76.78%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7716	77.16%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.7887	78.87%
Skin irritation	-	0.6186	61.86%
Skin corrosion	-	0.8550	85.50%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5565	55.65%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5823	58.23%
skin sensitisation	-	0.8252	82.52%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7013	70.13%
Acute Oral Toxicity (c)	III	0.5728	57.28%
Estrogen receptor binding	+	0.5883	58.83%
Androgen receptor binding	+	0.5542	55.42%
Thyroid receptor binding	-	0.5808	58.08%
Glucocorticoid receptor binding	-	0.5948	59.48%
Aromatase binding	-	0.5555	55.55%
PPAR gamma	+	0.6502	65.02%
Honey bee toxicity	-	0.9643	96.43%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.7900	79.00%
Fish aquatic toxicity	+	0.6457	64.57%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3923	Q9Y2I1	Nischarin	148 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.98%	95.56%
CHEMBL240	Q12809	HERG	94.91%	89.76%
CHEMBL3310	Q96DB2	Histone deacetylase 11	94.11%	88.56%
CHEMBL2581	P07339	Cathepsin D	92.00%	98.95%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	90.81%	85.49%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.79%	93.99%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.68%	90.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.96%	96.09%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	86.62%	96.42%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	86.15%	90.71%
CHEMBL4302	P08183	P-glycoprotein 1	86.14%	92.98%
CHEMBL3902	P09211	Glutathione S-transferase Pi	85.51%	93.81%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.25%	91.71%
CHEMBL2535	P11166	Glucose transporter	84.72%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.37%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.81%	94.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.20%	99.23%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.61%	96.67%

Plants that contains it

• Areca catechu
• Carex brevicollis
• Cephalanthus natalensis
• Commelina communis
• Crocus sativus
• Croton heliotropiifolius
• Elaeagnus angustifolia
• Guiera senegalensis
• Kopsia griffithii
• Nicotiana tabacum
• Ophiorrhiza kuroiwai
• Panax ginseng
• Passiflora alata
• Passiflora caerulea
• Passiflora incarnata
• Peganum harmala
• Polygala tenuifolia
• Rauvolfia sumatrana
• Simira salvadorensis
• Strychnos johnsonii
• Strychnos usambarensis
• Symplocos setchuensis
• Tribulus terrestris

Cross-Links

• PubChem: 160510
• LOTUS: LTS0027115
• wikiData: Q104667271