Harmol

Details

• Internal ID: a8d478f6-a61a-41ce-81b8-6013cb71606a
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: 1-methyl-2,9-dihydropyrido[3,4-b]indol-7-one
• SMILES (Canonical): CC1=C2C(=C3C=CC(=O)C=C3N2)C=CN1
• SMILES (Isomeric): CC1=C2C(=C3C=CC(=O)C=C3N2)C=CN1
• InChI: InChI=1S/C12H10N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-6,13-14H,1H3
• InChI Key: LBBJNGFCXDOYMQ-UHFFFAOYSA-N
• Popularity: 340 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₀N₂O
• Molecular Weight: 198.22 g/mol
• Exact Mass: 198.079312947 g/mol
• Topological Polar Surface Area (TPSA): 41.10 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 2.32
• H-Bond Acceptor: 1
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 487-03-6
• 1-methyl-9H-pyrido[3,4-b]indol-7-ol
• 9H-Pyrido[3,4-b]indol-7-ol, 1-methyl-
• 1-Methyl-9H-beta-carbolin-7-ol
• NSC 72292
• 1-methyl-2,9-dihydropyrido[3,4-b]indol-7-one
• MLS000736795
• 1-Methyl-9H-pyrido(3,4-b)indol-7-ol
• CHEMBL14285
• 7PQ075MCA6
• EINECS 207-645-9
• NSC-72292
• SMR000528328
• 9H-Pyrido(3,4-b)indol-7-ol, 1-methyl-
• 1-methyl-9~{H}-pyrido[3,4-b]indol-7-ol
• Methylpyridoindolol
• 1-methylbeta-carbolin-7-ol
• SR-01000761196
• 7-Hydroxyharman
• MFCD00834164
• Spectrum_000339
• SpecPlus_000452
• Prestwick0_000612
• Prestwick1_000612
• Prestwick2_000612
• Prestwick3_000612
• Spectrum2_000504
• Spectrum3_001531
• Spectrum4_000214
• Spectrum5_000853
• 7-Hydroxy-1-methyl-9H-pyrido[3,4-b]indole
• NCIOpen2_000349
• UNII-7PQ075MCA6
• BSPBio_000544
• BSPBio_002942
• KBioGR_000847
• KBioSS_000819
• cid_68094
• DivK1c_006548
• SCHEMBL177685
• SPBio_000427
• SPBio_002763
• BPBio1_000600
• CHEMBL486817
• SCHEMBL10024119
• 1-Methyl-9H-?-carbolin-7-ol
• BDBM55885
• CHEBI:95347
• KBio1_001492
• KBio2_000819
• KBio2_003387
• KBio2_005955
• KBio3_002442
• DTXSID10876697
• DTXSID10960989
• CHEBI:192558
• 1-methyl-7-hydroxy-beta-carboline
• 7-hydroxyl-1-methyl-beta-carboline
• NSC72292
• TNP00139
• beta 7-Hydroxy-1-methyl--Carboline
• 1-Methyl-9H-beta-carbolin-7-ol #
• BDBM50047009
• BDBM50498226
• STL565076
• AKOS006227799
• CCG-214814
• SDCCGMLS-0066699.P001
• CID 5280952
• NSC 72292 Monohydrochloride Dihydrate
• .beta.-Carboline, 7-hydroxy-1-methyl-
• NCGC00017250-01
• NCGC00017250-02
• NCGC00142521-01
• NCI60_013489
• WS-02001
• 1-methyl-2,9-dihydro-beta-carbolin-7-one
• HY-107811
• LS-194801
• 1-Methyl-9H-beta-carbolin-7-ol (harmalol)
• AB00053725
• CS-0030686
• FT-0603420
• H1360
• 1-Methyl-9H-pyrido[3,4-b]indol-7-ol, 9CI
• H-1300
• T72515
• A1-00784
• SR-01000761196-4
• 1-Methyl-2,9-dihydro-7H-pyrido[3,4-b]indol-7-one
• BRD-K01225247-003-02-2
• BRD-K01225247-311-03-7
• Q15411005
• 9H-Pyrido(3,4-b)indol-7-ol, 1-methyl- (8CI)(9CI)
• 1-Methyl-9H-pyrido[3,4-b]indol-7-ol Monohydrochloride Dihydrate
• HFI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.8706	87.06%
Blood Brain Barrier	+	0.6629	66.29%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8023	80.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9112	91.12%
OATP1B3 inhibitior	+	0.9642	96.42%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5474	54.74%
P-glycoprotein inhibitior	-	0.9386	93.86%
P-glycoprotein substrate	-	0.8729	87.29%
CYP3A4 substrate	-	0.5903	59.03%
CYP2C9 substrate	-	0.5918	59.18%
CYP2D6 substrate	-	0.8477	84.77%
CYP3A4 inhibition	-	0.6463	64.63%
CYP2C9 inhibition	-	0.8796	87.96%
CYP2C19 inhibition	-	0.8992	89.92%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.8732	87.32%
CYP inhibitory promiscuity	-	0.5137	51.37%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9423	94.23%
Carcinogenicity (trinary)	Non-required	0.5257	52.57%
Eye corrosion	-	0.9888	98.88%
Eye irritation	+	0.7175	71.75%
Skin irritation	-	0.8167	81.67%
Skin corrosion	-	0.9648	96.48%
Ames mutagenesis	+	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7143	71.43%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.9006	90.06%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6863	68.63%
Acute Oral Toxicity (c)	III	0.7007	70.07%
Estrogen receptor binding	+	0.8338	83.38%
Androgen receptor binding	+	0.8284	82.84%
Thyroid receptor binding	+	0.5461	54.61%
Glucocorticoid receptor binding	+	0.8752	87.52%
Aromatase binding	+	0.8231	82.31%
PPAR gamma	+	0.6289	62.89%
Honey bee toxicity	-	0.9429	94.29%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	-	0.6511	65.11%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	35481.3 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2524	P06280	Alpha-galactosidase A	44668.4 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	25118.9 nM	Potency	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	25118.9 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	15848.9 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	15848.9 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	28183.8 nM	Potency	via CMAUP
CHEMBL4376	Q92630	Dual-specificity tyrosine-phosphorylation regulated kinase 2	1500 nM	IC50	PMID: 22335895
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	8912.5 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM; 35481.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	7.9 nM; 7.9 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1075163	Q8TF76	Serine/threonine-protein kinase haspin	770 nM; 770 nM	IC50; IC50	via Super-PRED; PMID: 22335895

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.88%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.89%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	93.19%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.65%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	90.54%	94.75%
CHEMBL1951	P21397	Monoamine oxidase A	88.98%	91.49%
CHEMBL255	P29275	Adenosine A2b receptor	88.45%	98.59%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.67%	89.00%
CHEMBL1907	P15144	Aminopeptidase N	85.14%	93.31%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	84.75%	85.30%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.02%	93.03%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.14%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.88%	94.00%

Plants that contains it

• Banisteriopsis caapi
• Elaeagnus angustifolia
• Festuca pratensis
• Fontinalis squamosa
• Gentiana lutea
• Hippophae rhamnoides
• Passiflora edulis
• Passiflora foetida
• Passiflora incarnata
• Peganum harmala
• Tribulus terrestris

Cross-Links

• PubChem: 68094
• NPASS: NPC291389
• ChEMBL: CHEMBL486817
• LOTUS: LTS0023194
• wikiData: Q15411005