Harmalol

Details

• Internal ID: f2d74290-9bc5-4d07-a0c1-8bc40abbb2c2
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: 1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indol-7-ol
• SMILES (Canonical): CC1=NCCC2=C1NC3=C2C=CC(=C3)O
• SMILES (Isomeric): CC1=NCCC2=C1NC3=C2C=CC(=C3)O
• InChI: InChI=1S/C12H12N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-3,6,14-15H,4-5H2,1H3
• InChI Key: RHVPEFQDYMMNSY-UHFFFAOYSA-N
• Popularity: 82 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₂N₂O
• Molecular Weight: 200.24 g/mol
• Exact Mass: 200.094963011 g/mol
• Topological Polar Surface Area (TPSA): 48.40 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.24
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 525-57-5
• Harmidol
• Harmolol
• 1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indol-7-ol
• 1-Methyl-4,9-dihydro-3H-beta-carbolin-7-ol
• 4,9-Dihydro-1-methyl-3H-pyrido(3,4-b)indol-7-ol
• 3H-Pyrido[3,4-b]indol-7-ol, 4,9-dihydro-1-methyl-
• CHEMBL129177
• CHEBI:27943
• 2NQN80556Q
• 11-Hydroxyharmalan; NSC 72293
• NSC-72293
• 4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indol-7-ol
• 3H-Pyrido(3,4-b)indol-7-ol, 4,9-dihydro-1-methyl-
• 1-Methyl-4,9-dihydro-3H-beta-carbolin-7-ol hydrochloride
• MLS002153909
• SMR001233258
• EINECS 208-375-4
• UNII-2NQN80556Q
• SR-01000636961
• NSC 72293
• HARMALOLHCL
• Spectrum_000421
• 1-methyl-3,4-dihydrobeta-carbolin-7-ol
• HARMALOL [MI]
• Prestwick0_000611
• Prestwick1_000611
• Prestwick2_000611
• Prestwick3_000611
• Spectrum2_000556
• Spectrum3_000721
• Spectrum4_000767
• Spectrum5_001307
• bmse000988
• bmse001010
• BSPBio_000542
• BSPBio_002242
• KBioGR_001154
• KBioSS_000901
• BIDD:ER0514
• DivK1c_000998
• SCHEMBL555401
• SPBio_000631
• SPBio_002761
• BPBio1_000598
• SCHEMBL15821030
• BDBM60980
• KBio1_000998
• KBio2_000901
• KBio2_003469
• KBio2_006037
• KBio3_001462
• DTXSID50894870
• DTXSID90975692
• cid_16667410
• CRQDWQWZCNKKAC-UHFFFAOYSA-N
• NINDS_000998
• RHVPEFQDYMMNSY-UHFFFAOYSA-N
• NSC72293
• TNP00138
• BDBM50132101
• MFCD00152093
• AKOS005202957
• SDCCGMLS-0066705.P001
• IDI1_000998
• SMP1_000145
• 3H-Pyrido[3, 4,9-dihydro-1-methyl-
• NCGC00017249-01
• NCGC00017249-02
• NCGC00142520-01
• NCI60_013481
• 1-Methyl-4,9-dihydro-3H-?-carbolin-7-ol
• 3,4-Dihydro-7-hydroxy-1-methyl-b-carboline
• FT-0608067
• FT-0626857
• C06537
• H-1108
• A1-00785
• SR-01000636961-5
• 3,4-Dihydro-1-methyl-2H-Pyrido[3,4-b]indol-7-ol
• BRD-K14756138-001-01-9
• BRD-K14756138-003-02-3
• BRD-K14756138-310-03-0
• Q15138221
• 2H-Pyrido[3,4-b]indol-7-ol, 3,4-dihydro-1-methyl-
• 3,4-DIHYDRO-1-METHYL-9H-PYRIDO(3,4-B)INDOL-7-OL
• 4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indol-7-ol, 9CI
• 1-Methyl-2,3,4,9-tetrahydro-7H-pyrido[3,4-b]indol-7-one
• 1-methyl-2,3,4,9-tetrahydro-beta-carbolin-7-one;hydrate;hydrochloride
• 1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indol-7-one;hydrate;hydrochloride

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9862	98.62%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	+	0.7879	78.79%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6579	65.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9352	93.52%
OATP1B3 inhibitior	+	0.9403	94.03%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.6500	65.00%
BSEP inhibitior	-	0.7439	74.39%
P-glycoprotein inhibitior	-	0.9613	96.13%
P-glycoprotein substrate	-	0.7546	75.46%
CYP3A4 substrate	+	0.5450	54.50%
CYP2C9 substrate	+	0.5973	59.73%
CYP2D6 substrate	-	0.7987	79.87%
CYP3A4 inhibition	-	0.6113	61.13%
CYP2C9 inhibition	-	0.9047	90.47%
CYP2C19 inhibition	-	0.8075	80.75%
CYP2D6 inhibition	+	0.7615	76.15%
CYP1A2 inhibition	+	0.7557	75.57%
CYP2C8 inhibition	+	0.5082	50.82%
CYP inhibitory promiscuity	-	0.5706	57.06%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6748	67.48%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.5454	54.54%
Skin irritation	-	0.7523	75.23%
Skin corrosion	-	0.9004	90.04%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7399	73.99%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8308	83.08%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8661	86.61%
Acute Oral Toxicity (c)	III	0.5634	56.34%
Estrogen receptor binding	+	0.6449	64.49%
Androgen receptor binding	+	0.8109	81.09%
Thyroid receptor binding	+	0.5314	53.14%
Glucocorticoid receptor binding	+	0.6336	63.36%
Aromatase binding	+	0.5995	59.95%
PPAR gamma	+	0.7728	77.28%
Honey bee toxicity	-	0.9679	96.79%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	-	0.6432	64.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	95.36%	91.79%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	94.75%	91.71%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.88%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.18%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.08%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.69%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.06%	96.09%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	90.51%	85.49%
CHEMBL2535	P11166	Glucose transporter	89.28%	98.75%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	87.77%	93.10%
CHEMBL3310	Q96DB2	Histone deacetylase 11	86.27%	88.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.54%	93.40%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.40%	93.99%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.39%	90.08%
CHEMBL1951	P21397	Monoamine oxidase A	84.04%	91.49%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	83.42%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.35%	94.00%
CHEMBL242	Q92731	Estrogen receptor beta	82.27%	98.35%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.20%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.71%	89.00%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	81.12%	96.42%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	80.44%	95.70%

Plants that contains it

• Anacardium occidentale
• Banisteriopsis caapi
• Passiflora edulis
• Passiflora incarnata
• Peganum harmala

Cross-Links

• PubChem: 3565
• LOTUS: LTS0116566
• wikiData: Q15138221