Harman

Details

• Internal ID: c93e8a63-dedc-4a10-a344-a7b14f05df64
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: 1-methyl-9H-pyrido[3,4-b]indole
• SMILES (Canonical): CC1=NC=CC2=C1NC3=CC=CC=C23
• SMILES (Isomeric): CC1=NC=CC2=C1NC3=CC=CC=C23
• InChI: InChI=1S/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3
• InChI Key: PSFDQSOCUJVVGF-UHFFFAOYSA-N
• Popularity: 3,691 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₀N₂
• Molecular Weight: 182.22 g/mol
• Exact Mass: 182.084398327 g/mol
• Topological Polar Surface Area (TPSA): 28.70 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.02
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• HARMANE
• 486-84-0
• 1-Methyl-9H-pyrido[3,4-b]indole
• Aribine
• Loturine
• Locuturine
• 1-Methyl-9H-beta-carboline
• Aribin
• Passiflorin
• 1-Methylnorharman
• Locuturin
• 3-Methyl-4-carboline
• 9H-Pyrido[3,4-b]indole, 1-methyl-
• PYRIDOBINDOLE, L-METHYL-
• 1-methyl-2-carboline
• 1-Methyl-beta-carboline
• 1-Methyl-9H-pyrido(3,4-b)indole
• NSC 54439
• 9H-Pyrido(3,4-b)indole, 1-methyl-
• Harman-d3
• CCRIS 6419
• EINECS 207-642-2
• Passiflorin-13C2,15N
• 1-Methyl-.beta.-carboline
• BRN 0143898
• CHEMBL12014
• CHEBI:5623
• UNII-82D6J0535P
• NSC54439
• NSC-54439
• 82D6J0535P
• Harman-d3 (Major)
• Harman-13C2,15N
• 5-23-08-00261 (Beilstein Handbook Reference)
• 1189461-56-0
• 1-Methyl-9H-pyrid(3,4-b)indole
• 1-Methyl-9H-pyrid[3,4-b]indole
• methylbeta-carboline
• SR-01000075915
• MFCD00004957
• Passiflorine
• Zygofabagine
• Cyanoaceticacid-Osu
• CN9
• Harmane, free base
• L-methylpyridobindole
• Harmane, 98%
• L-Methyl-Pyridobindole
• Spectrum_001126
• Tocris-1132
• ST013856
• SpecPlus_000609
• Prestwick0_000620
• Prestwick1_000620
• Prestwick2_000620
• Prestwick3_000620
• Spectrum3_000905
• Spectrum4_001003
• HARMAN [MI]
• Lopac-H-7258
• Harmane ( 1-Methyl-9H-pyrido[3,4-b]indole)
• Lopac0_000605
• Oprea1_152883
• BSPBio_000560
• KBioGR_001465
• KBioSS_001606
• MLS001173587
• DivK1c_006705
• SCHEMBL141723
• SPECTRUM1500866
• SPBio_002779
• 1-Methyl-9H-I(2)-carboline
• AMY211
• BPBio1_000616
• 1-Methyl-9H-beta-carboline #
• cid_5281404
• KBio1_001649
• KBio2_001606
• KBio2_004174
• KBio2_006742
• KBio3_001850
• DTXSID80197568
• HMS2858P09
• HMS3261J12
• HMS3267O04
• HMS3412K19
• HMS3676K19
• WLN: T B656 EN HMJ F
• BCP31368
• Tox21_500605
• BDBM50013786
• HB1665
• STK501254
• 1-Methyl-9H-Pyrido[3,4-6]indole
• 1-Methyl-9H-beta-carboline (Harman)
• AKOS002664659
• CCG-204694
• LP00605
• SDCCGMLS-0066938.P001
• SDCCGSBI-0050587.P003
• NCGC00015514-01
• NCGC00015514-02
• NCGC00015514-03
• NCGC00015514-04
• NCGC00015514-05
• NCGC00015514-06
• NCGC00015514-07
• NCGC00015514-08
• NCGC00015514-09
• NCGC00015514-10
• NCGC00015514-16
• NCGC00025022-01
• NCGC00025022-02
• NCGC00025022-03
• NCGC00025022-04
• NCGC00025022-05
• NCGC00025022-06
• NCGC00261290-01
• AC-15673
• AS-42735
• SMR000538681
• 1-Methyl-9H-pyrido[3,4-b]indole, 9CI
• CAS-21655-84-5
• HY-101392
• LS-133553
• AB00052849
• BB 0254238
• CS-0021283
• EU-0100605
• FT-0626859
• C09209
• H 7258
• H-1150
• SR-01000075915-1
• SR-01000075915-7
• SR-01000075915-8
• BRD-K12630395-003-03-8
• Q15411006
• InChI=1/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.9372	93.72%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6574	65.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9479	94.79%
OATP1B3 inhibitior	+	0.9620	96.20%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5240	52.40%
P-glycoprotein inhibitior	-	0.9616	96.16%
P-glycoprotein substrate	-	0.8741	87.41%
CYP3A4 substrate	-	0.5513	55.13%
CYP2C9 substrate	-	0.8132	81.32%
CYP2D6 substrate	-	0.7428	74.28%
CYP3A4 inhibition	+	0.6522	65.22%
CYP2C9 inhibition	-	0.9044	90.44%
CYP2C19 inhibition	-	0.7432	74.32%
CYP2D6 inhibition	+	0.6772	67.72%
CYP1A2 inhibition	+	0.9189	91.89%
CYP2C8 inhibition	+	0.4857	48.57%
CYP inhibitory promiscuity	+	0.6216	62.16%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6423	64.23%
Eye corrosion	-	0.9474	94.74%
Eye irritation	+	0.8365	83.65%
Skin irritation	+	0.6175	61.75%
Skin corrosion	-	0.9024	90.24%
Ames mutagenesis	+	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6023	60.23%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	+	0.6574	65.74%
skin sensitisation	-	0.8443	84.43%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.7558	75.58%
Acute Oral Toxicity (c)	III	0.7770	77.70%
Estrogen receptor binding	+	0.8220	82.20%
Androgen receptor binding	+	0.6963	69.63%
Thyroid receptor binding	+	0.5496	54.96%
Glucocorticoid receptor binding	+	0.6018	60.18%
Aromatase binding	+	0.6616	66.16%
PPAR gamma	-	0.5445	54.45%
Honey bee toxicity	-	0.9673	96.73%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.7700	77.00%
Fish aquatic toxicity	-	0.5246	52.46%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	31622.8 nM; 22387.2 nM; 12589.3 nM; 35481.3 nM; 28183.8 nM	Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	31622.8 nM; 28183.8 nM; 31622.8 nM; 25118.9 nM; 28183.8 nM	Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	19952.6 nM	Potency	via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	630.96 nM; 1258.93 nM	AC50; AC50	via CMAUP; via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	3981.1 nM; 3981.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	35481.3 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	25118.9 nM; 31622.8 nM; 25118.9 nM; 15848.9 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	31622.8 nM; 31622.8 nM; 28183.8 nM; 22387.2 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	562.3 nM; 562.3 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	5011.9 nM	Potency	via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	1995.3 nM; 1995.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	97.95%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.34%	95.56%
CHEMBL3524	P56524	Histone deacetylase 4	88.71%	92.97%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	87.99%	93.65%
CHEMBL3401	O75469	Pregnane X receptor	86.57%	94.73%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	86.50%	96.47%
CHEMBL255	P29275	Adenosine A2b receptor	86.47%	98.59%
CHEMBL3310	Q96DB2	Histone deacetylase 11	86.34%	88.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.29%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.79%	89.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.70%	94.62%
CHEMBL1937	Q92769	Histone deacetylase 2	85.38%	94.75%
CHEMBL2581	P07339	Cathepsin D	85.32%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.29%	93.99%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	85.07%	93.10%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	84.18%	85.49%
CHEMBL1781	P11387	DNA topoisomerase I	83.70%	97.00%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	83.30%	85.00%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	83.29%	90.71%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	83.07%	96.39%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.36%	94.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.28%	96.67%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.35%	94.80%

Plants that contains it

• Areca catechu
• Capsicum annuum
• Carex brevicollis
• Cephalanthus natalensis
• Commelina communis
• Crocus sativus
• Croton heliotropiifolius
• Elaeagnus angustifolia
• Guiera senegalensis
• Hippophae rhamnoides
• Kopsia griffithii
• Nauclea diderrichii
• Nicotiana tabacum
• Ophiorrhiza japonica
• Ophiorrhiza kuroiwai
• Panax ginseng
• Passiflora alata
• Passiflora edulis
• Passiflora incarnata
• Peganum harmala
• Phyllodium pulchellum
• Plumbago zeylanica
• Polygala tenuifolia
• Rauvolfia sellowii
• Rauvolfia sumatrana
• Rauvolfia verticillata
• Rumex chalepensis
• Simira eliezeriana
• Simira mexicana
• Simira salvadorensis
• Strychnos johnsonii
• Strychnos usambarensis
• Symplocos setchuensis
• Tribulus terrestris
• Uncaria elliptica
• Uncaria rhynchophylla
• Viola philippica

Cross-Links

• PubChem: 5281404
• NPASS: NPC179787
• ChEMBL: CHEMBL12014
• LOTUS: LTS0068205
• wikiData: Q15411006