Leonurine

Details

• Internal ID: 0c6dfc4f-c85c-4ea7-9ffe-2d204ac53f07
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Hydroxybenzoic acid derivatives > Gallic acid and derivatives
• IUPAC Name: 4-(diaminomethylideneamino)butyl 4-hydroxy-3,5-dimethoxybenzoate
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C(=O)OCCCCN=C(N)N
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)C(=O)OCCCCN=C(N)N
• InChI: InChI=1S/C14H21N3O5/c1-20-10-7-9(8-11(21-2)12(10)18)13(19)22-6-4-3-5-17-14(15)16/h7-8,18H,3-6H2,1-2H3,(H4,15,16,17)
• InChI Key: WNGSUWLDMZFYNZ-UHFFFAOYSA-N
• Popularity: 134 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₁N₃O₅
• Molecular Weight: 311.33 g/mol
• Exact Mass: 311.14812078 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.62
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• 24697-74-3
• Leonurine hydrochloride
• 4-GUANIDINOBUTYL 4-HYDROXY-3,5-DIMETHOXYBENZOATE
• 4-Guanidino-n-butyl syringate
• SCM-198
• 4-(diaminomethylideneamino)butyl 4-hydroxy-3,5-dimethoxybenzoate
• C14H21N3O5
• UNII-09Q5W34QDA
• 09Q5W34QDA
• CHEBI:80843
• Benzoic acid, 4-hydroxy-3,5-dimethoxy-, 4-[(aminoiminomethyl)amino]butyl ester
• Benzoic acid, 4-hydroxy-3,5-dimethoxy-, ester with (4-hydroxybutyl)guanidine
• Benzoic acid, 4-hydroxy-3,5-dimethoxy-, 4-((aminoiminomethyl)amino)butyl ester
• 20027-21-8
• Leonurine-hydrochloride
• LEONURINE [MI]
• 4-Guanidinobutyl syringate
• D08KHD
• 4-carbamimidamidobutyl 4-hydroxy-3,5-dimethoxybenzoate
• SCHEMBL2685302
• 4-guanidino-1-butanol syringate
• CHEMBL1290284
• DTXSID70179434
• BCP30159
• HY-N0741
• MFCD09839432
• s3890
• AKOS015920020
• AKOS025395615
• CCG-267591
• CS-6071
• DS-1032
• FT-0659198
• C16985
• SCM-198 pound>>SCM198 pound>>SCM 198
• Q410290
• SYRINGIC ACID .DELTA.-GUANIDINOBUTYL ESTER
• (4-(4-HYDROXY-3,5-DIMETHOXYBENZOYLOXY)BUTYL)GUANIDINE
• 4-Guanidinobutyl 4-hydroxy-3,5-dimethoxybenzoate xhydrochloride
• 4-hydroxy-3,5-dimethoxybenzoic acid delta-guanidinobutyl ester
• 4-[(diaminomethylidene)amino]butyl 4-hydroxy-3,5-dimethoxybenzoate
• 4-HYDROXY-3,5-DIMETHOXYBENZOIC ACID .DELTA.-GUANIDINOBUTYL ESTER
• 4-Hydroxy-3,5-dimethoxybenzoic acid 4-[(aminoiminomethyl)amino]butyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9051	90.51%
Caco-2	+	0.5440	54.40%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8766	87.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8373	83.73%
OATP1B3 inhibitior	+	0.9449	94.49%
MATE1 inhibitior	+	0.6000	60.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.7202	72.02%
P-glycoprotein inhibitior	-	0.7994	79.94%
P-glycoprotein substrate	-	0.5914	59.14%
CYP3A4 substrate	-	0.5153	51.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7746	77.46%
CYP3A4 inhibition	-	0.8942	89.42%
CYP2C9 inhibition	-	0.8574	85.74%
CYP2C19 inhibition	-	0.8259	82.59%
CYP2D6 inhibition	-	0.8532	85.32%
CYP1A2 inhibition	+	0.6092	60.92%
CYP2C8 inhibition	+	0.5872	58.72%
CYP inhibitory promiscuity	-	0.9196	91.96%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8023	80.23%
Carcinogenicity (trinary)	Non-required	0.6352	63.52%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.8165	81.65%
Skin irritation	-	0.7743	77.43%
Skin corrosion	-	0.9258	92.58%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5228	52.28%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.5789	57.89%
skin sensitisation	-	0.8408	84.08%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7416	74.16%
Acute Oral Toxicity (c)	III	0.6121	61.21%
Estrogen receptor binding	+	0.8644	86.44%
Androgen receptor binding	-	0.5533	55.33%
Thyroid receptor binding	+	0.6449	64.49%
Glucocorticoid receptor binding	+	0.8378	83.78%
Aromatase binding	+	0.7816	78.16%
PPAR gamma	+	0.5830	58.30%
Honey bee toxicity	-	0.9562	95.62%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6533	65.33%
Fish aquatic toxicity	-	0.5308	53.08%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.51%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.69%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.28%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.84%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.97%	96.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.68%	90.71%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	88.01%	97.88%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	85.36%	94.42%
CHEMBL2535	P11166	Glucose transporter	85.01%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.40%	94.45%
CHEMBL3474	P14555	Phospholipase A2 group IIA	81.85%	94.05%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.51%	96.95%
CHEMBL4208	P20618	Proteasome component C5	80.60%	90.00%
CHEMBL3194	P02766	Transthyretin	80.04%	90.71%

Plants that contains it

• Cistanche deserticola
• Leonurus japonicus
• Leonurus sibiricus
• Rehmannia glutinosa

Cross-Links

• PubChem: 161464
• NPASS: NPC254053
• LOTUS: LTS0262707
• wikiData: Q410290