Harmaline

Details

• Internal ID: adc3947d-0e96-4dd8-9e8b-6f7fa0154949
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: 7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
• SMILES (Canonical): CC1=NCCC2=C1NC3=C2C=CC(=C3)OC
• SMILES (Isomeric): CC1=NCCC2=C1NC3=C2C=CC(=C3)OC
• InChI: InChI=1S/C13H14N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7,15H,5-6H2,1-2H3
• InChI Key: RERZNCLIYCABFS-UHFFFAOYSA-N
• Popularity: 893 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₄N₂O
• Molecular Weight: 214.26 g/mol
• Exact Mass: 214.110613074 g/mol
• Topological Polar Surface Area (TPSA): 37.40 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.54
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 304-21-2
• Dihydroharmine
• Harmidine
• Armalin
• Harmalol methyl ether
• O-Methylharmalol
• 3,4-Dihydroharmine
• Harmine, dihydro-
• 3H-Pyrido[3,4-b]indole, 4,9-dihydro-7-methoxy-1-methyl-
• 7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
• harmalin
• NSC 407285
• 1-Methyl-7-methoxy-3,4-dihydro-beta-carboline
• 3H-Pyrido(3,4-b)indole, 4,9-dihydro-7-methoxy-1-methyl-
• 7-Methoxy-1-methyl-4,9-dihydro-3H-beta-carboline
• 4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido(3,4-b)indole
• 7-methoxy-1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole
• CN58I4TOET
• 3,4-Dihydro-7-methoxy-1-methyl-9-pyrid(3,4-b)indole
• 3,4-Dihydro-7-methoxy-1-methyl-9-pyrido(3,4-b)indole
• MLS000028746
• 4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole
• CHEMBL340807
• CHEBI:28172
• TNP00101
• NSC-407285
• SMR000058221
• 7-methoxy-1-methyl-4,9-dihydro-3H-b-carboline
• 1-Methyl-7-methoxy-3,4-dihydro-.beta.-carboline
• SR-01000721899
• EINECS 206-152-6
• UNII-CN58I4TOET
• 3,4-Dihydro-7-methoxy-1-methyl-9-pyrid[3,4-b]indole
• BRN 0207310
• Dihydro-Harmine
• 7-METHOXY-1-METHYL-4,9-DIHYDRO-3H-PYRIDO(3,4-B)INDOLE
• HSDB 7645
• MFCD00004955
• 3,4-b]indole
• 3, 4-Dihydroharmine
• Spectrum_000301
• Opera_ID_665
• HARMALINE [MI]
• HARMALINE [HSDB]
• Prestwick0_000610
• Prestwick1_000610
• Prestwick2_000610
• Prestwick3_000610
• Spectrum2_000411
• Spectrum3_000720
• Spectrum4_000824
• Spectrum5_001452
• 7-methoxy-1-methyl-3,4-dihydrobeta-carboline
• HARMALINE [MART.]
• 1-Methyl-7-methoxy-3,4-dihydro- beta-carboline
• Oprea1_112644
• BSPBio_000520
• BSPBio_002539
• KBioGR_001367
• KBioSS_000781
• MLS001148231
• BIDD:ER0444
• DivK1c_000950
• SCHEMBL199260
• SPECTRUM1500864
• SPBio_000362
• SPBio_002739
• BPBio1_000572
• MEGxp0_001874
• SCHEMBL3862598
• DTXSID8041038
• ACon1_000019
• CHEBI:95328
• HMS502P12
• KBio1_000950
• KBio2_000781
• KBio2_003349
• KBio2_005917
• KBio3_001759
• NINDS_000950
• HMS1921K22
• HMS2233L23
• HMS3371G17
• HMS3885P22
• BDBM50029799
• CCG-38677
• NSC407285
• NSC789037
• s4776
• AKOS015904564
• AKOS026750619
• DB13875
• KS-5325
• NSC-789037
• SDCCGMLS-0066716.P001
• IDI1_000950
• NCGC00017221-01
• NCGC00017221-02
• NCGC00017221-03
• NCGC00017221-04
• NCGC00017221-05
• NCGC00017221-06
• NCGC00017221-07
• NCGC00094867-01
• NCGC00094867-02
• NCGC00094867-03
• NCGC00094867-04
• NCGC00094867-05
• NCGC00094867-06
• AC-34436
• LS-14204
• PD056221
• WLN: T B656 DM HM CHJ F1 KO1
• HY-107828
• 3,4-Dihydro-7-methoxy-1-methyl-b-carboline
• CS-0030704
• FT-0626855
• H1237
• 3,4-Dihydro-7-methoxy-1-methyl-beta-carboline
• C06536
• H-1100
• H-1102
• 1-Methyl-7-methoxy-3,4-dihydro-beta -carboline
• 1-Methyl-7-methoxy-3, 4-dihydro-beta -carboline
• 3H-Pyrido[3, 4,9-dihydro-7-methoxy-1-methyl-
• 7-Methoxy-1-methyl-4,9-dihydro-3H-?-carboline
• A820367
• Q135270
• 7-Methoxy-1-methyl-2,9-dihydro-1H-beta-carboline
• 7-methoxy-1-methyl-3,4-dihydro-2h-beta-carboline
• A1-00783
• SR-01000721899-4
• SR-01000721899-5
• 7-Methoxy-1-methyl-4,9-dihydro-3H-beta-carboline #
• BRD-K91317041-001-03-8
• BRD-K91317041-310-03-3
• 3,4-Dihydro-7-methoxy-1-methyl-9H-pyrid[3,4-b]indole
• 3,4-Dihydro-7-methoxy-1-methyl-9H-pyrido[3,4-b]indole

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	-	0.9372	93.72%
Blood Brain Barrier	+	0.8879	88.79%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7208	72.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9488	94.88%
OATP1B3 inhibitior	+	0.9388	93.88%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.7750	77.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.9677	96.77%
P-glycoprotein substrate	-	0.8005	80.05%
CYP3A4 substrate	+	0.5782	57.82%
CYP2C9 substrate	+	0.5701	57.01%
CYP2D6 substrate	-	0.7639	76.39%
CYP3A4 inhibition	+	0.6622	66.22%
CYP2C9 inhibition	-	0.9282	92.82%
CYP2C19 inhibition	-	0.9062	90.62%
CYP2D6 inhibition	+	0.8892	88.92%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.6176	61.76%
CYP inhibitory promiscuity	-	0.5840	58.40%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6710	67.10%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.7511	75.11%
Skin irritation	-	0.7390	73.90%
Skin corrosion	-	0.9005	90.05%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5250	52.50%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8670	86.70%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8719	87.19%
Acute Oral Toxicity (c)	III	0.5676	56.76%
Estrogen receptor binding	+	0.7064	70.64%
Androgen receptor binding	+	0.7704	77.04%
Thyroid receptor binding	+	0.5657	56.57%
Glucocorticoid receptor binding	+	0.6831	68.31%
Aromatase binding	+	0.6815	68.15%
PPAR gamma	+	0.6472	64.72%
Honey bee toxicity	-	0.9368	93.68%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.7600	76.00%
Fish aquatic toxicity	-	0.6200	62.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.40%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.28%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.18%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.15%	96.09%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	92.67%	85.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.15%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.91%	94.45%
CHEMBL2535	P11166	Glucose transporter	90.71%	98.75%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	90.01%	91.71%
CHEMBL1907	P15144	Aminopeptidase N	89.27%	93.31%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	88.67%	80.96%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	87.84%	96.47%
CHEMBL1951	P21397	Monoamine oxidase A	86.81%	91.49%
CHEMBL2581	P07339	Cathepsin D	86.74%	98.95%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	86.40%	91.79%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.30%	93.40%
CHEMBL240	Q12809	HERG	86.27%	89.76%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.61%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.57%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.43%	97.09%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	84.19%	93.24%
CHEMBL4208	P20618	Proteasome component C5	83.84%	90.00%
CHEMBL5747	Q92793	CREB-binding protein	81.21%	95.12%

Plants that contains it

• Banisteriopsis caapi
• Oxalis tuberosa
• Passiflora foetida
• Peganum harmala

Cross-Links

• PubChem: 3564
• LOTUS: LTS0120934
• wikiData: Q104252234