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Harmaline

Family: Plantae - Zygophyllaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Beta-Carboline Alkaloid

Canonical Smiles	COc1ccc2=C3C(=C(C)NCC3)N=c2c1
InChI	InChI=1S/C13H14N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7,14H,5-6H2,1-2H3
InChIKey	QJOZJXNKVMFAET-UHFFFAOYSA-N
Formula	C₁₃H₁₄N₂O
HBA	3
HBD	1
MW	214.27
Rotatable Bonds	1
TPSA	33.62
LogP	0.7
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	16
Formal Charge	0
Fraction CSP3	0.31
Exact Mass	214.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Peganum harmala	Zygophyllaceae	Plantae	43879

Showing of synonyms

Nenaah G (2010). Antibacterial and antifungal activities of (beta)-carboline alkaloids of Peganum harmala (L) seeds and their combination effects. Fitoterapia,2010,81(7),779-782. [View] [PubMed]

Pubchem: 5280951

Gnps: CCMSLIB00004685114

CPRiL: 15937

SMILES: C1CNC=C(C1=c23)N=c2cccc3

Level: 0

Mol. Weight: 214.27 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp): -4.84
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.430
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.3

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.510
Plasma Protein Binding: 14.11
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 7.310
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.980
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.090
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.140
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 4.040
Rat (Acute): 2.240
Rat (Chronic Oral): 1.840
Fathead Minnow: 4.250
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 357.110
Hydration Free Energy: -9.130
Log(D) at pH=7.4: 1.880
Log(P): 1.69
Log S: -2.9
Log(Vapor Pressure): -5.42
Melting Point: 148.33
pKa Acid: 12.21
pKa Basic: 9.32

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9706
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9706
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9626
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9626
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9569
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9569
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.9516
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.9516
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.9355
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.9355
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9302
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9302
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9236
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9236
Amine oxidase [flavin-containing] B	P27338	AOFB_HUMAN	Homo sapiens	3	0.8975
Amine oxidase [flavin-containing] B	P27338	AOFB_HUMAN	Homo sapiens	3	0.8975
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.8856
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.8856
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8845
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8845
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8704
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8704
Catalase-peroxidase	Q3JNW6	KATG_BURP1	Burkholderia pseudomallei	3	0.8626
Catalase-peroxidase	Q3JNW6	KATG_BURP1	Burkholderia pseudomallei	3	0.8626
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.8462
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.8462
Uridine phosphorylase	Q5XA29	Q5XA29_STRP6	Streptococcus pyogenes serotype M6	3	0.7957
Uridine phosphorylase	Q5XA29	Q5XA29_STRP6	Streptococcus pyogenes serotype M6	3	0.7957
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7767
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7767
DNA topoisomerase 1	P06612	TOP1_ECOLI	Escherichia coli	3	0.7566
DNA topoisomerase 1	P06612	TOP1_ECOLI	Escherichia coli	3	0.7566
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7483
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7483
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7463
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7463
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7459
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7459
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7406
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7406
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7397
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7397
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1	Q9Y3Z3	SAMH1_HUMAN	Homo sapiens	3	0.7355
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1	Q9Y3Z3	SAMH1_HUMAN	Homo sapiens	3	0.7355
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7333
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7333
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7328
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7328
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7327
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7327
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7313
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7313
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	2	0.7308
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	2	0.7308
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7300
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7300
Bifunctional purine biosynthesis protein ATIC	P31335	PUR9_CHICK	Gallus gallus	3	0.7293
Bifunctional purine biosynthesis protein ATIC	P31335	PUR9_CHICK	Gallus gallus	3	0.7293
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	2	0.7288
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	2	0.7288
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7282
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7282
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7270
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7270
Cyclic nucleotide-gated potassium channel mll3241	Q98GN8	CNGK1_RHILO	Mesorhizobium japonicum)	2	0.7269
Cyclic nucleotide-gated potassium channel mll3241	Q98GN8	CNGK1_RHILO	Mesorhizobium japonicum)	2	0.7269
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7262
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7262
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7242
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7242
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7242
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7242
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7241
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7241
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7235
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7235
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7223
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7223
Rifampin ADP-ribosyl transferase	A0QRS5	A0QRS5_MYCS2	Mycolicibacterium smegmatis155)	3	0.7212
Rifampin ADP-ribosyl transferase	A0QRS5	A0QRS5_MYCS2	Mycolicibacterium smegmatis155)	3	0.7212
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7210
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7210
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7179
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7179
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	2	0.7177
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	2	0.7177
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	2	0.7176
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	2	0.7176
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7173
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7173
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7169
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7169
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7157
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7157
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	3	0.7148
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	3	0.7148
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7139
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7139
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	2	0.7134
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	2	0.7134
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7131
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7131
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7127
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7127
Peroxidase C1A	P00433	PER1A_ARMRU	Armoracia rusticana	3	0.7125
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7125
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7125
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7125
Peroxidase C1A	P00433	PER1A_ARMRU	Armoracia rusticana	3	0.7125
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7125
Glutamate receptor 3	P19492	GRIA3_RAT	Rattus norvegicus	3	0.7124
Glutamate receptor 3	P19492	GRIA3_RAT	Rattus norvegicus	3	0.7124
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7109
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7109
Ascorbate-specific PTS system EIIC component	P39301	ULAA_ECOLI	Escherichia coli	3	0.7094
Ascorbate-specific PTS system EIIC component	P39301	ULAA_ECOLI	Escherichia coli	3	0.7094
GMP reductase	Q81JJ9	GUAC_BACAN	Bacillus anthracis	2	0.7093
GMP reductase	Q81JJ9	GUAC_BACAN	Bacillus anthracis	2	0.7093
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	2	0.7091
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7091
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7091
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	2	0.7091
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7086
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7086
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7081
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7081
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7078
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7078
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7077
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7077
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7072
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7072
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7071
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7071
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7067
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7067
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	2	0.7055
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	2	0.7055
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7036
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7036
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7034
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7034
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	2	0.7026
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	2	0.7026
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7020
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7020
Glycoside Hydrolase Family 13	Q65MI2	Q65MI2_BACLD	Bacillus licheniformis	2	0.7010
Glycoside Hydrolase Family 13	Q65MI2	Q65MI2_BACLD	Bacillus licheniformis	2	0.7010
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7004
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7004
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7001
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7001

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