1-Methyl-L-histidine

Details

• Internal ID: 40526b86-6981-4aa4-a8fd-89a9de20156c
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Histidine and derivatives
• IUPAC Name: (2S)-2-amino-3-(1-methylimidazol-4-yl)propanoic acid
• SMILES (Canonical): CN1C=C(N=C1)CC(C(=O)O)N
• SMILES (Isomeric): CN1C=C(N=C1)C[C@@H](C(=O)O)N
• InChI: InChI=1S/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
• InChI Key: BRMWTNUJHUMWMS-LURJTMIESA-N
• Popularity: 543 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇H₁₁N₃O₂
• Molecular Weight: 169.18 g/mol
• Exact Mass: 169.085126602 g/mol
• Topological Polar Surface Area (TPSA): 81.10 Ų
• XlogP: -3.30
• Atomic LogP (AlogP): -0.63
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 332-80-9
• 1-Methylhistidine
• H-His(1-Me)-OH
• pi-methylhistidine
• N1-Methyl-L-histidine
• L-1-Methylhistidine
• L-Histidine, 1-methyl-
• 1-methyl histidine
• 4-Methyl-Histidine
• (S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid
• N|O-Methyl-L-histidine
• 1-N-Methyl-L-histidine
• 1 methylhistidine
• Histidine, 1-methyl-, L-
• 1-Methyl-Histidine
• CHEBI:50599
• 1-MHis
• 3-(1-Methylimidazol-4-yl)-L-alanine
• N(tele)-methyl-L-histidine
• (2S)-2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid
• CHEMBL1233327
• 3-Methyl-L-histidine (archaic)
• 583O01BJ32
• UNII-583O01BJ32
• NSC-524367
• HIC
• EINECS 206-368-0
• NSC 524367
• Nt-Methyl-L-histidine
• H-His(Ntau-Me)-OH
• Ntau-Methyl-L-histidine
• histidine, 1-Methyl-L-
• Histidine, N-tau-methyl-
• TELE-METHYLHISTIDINE
• bmse000449
• SCHEMBL52216
• .TAU.-METHYLHISTIDINE
• 1-methyl histidine (L-form)
• DTXSID50186848
• L-Histidine, 1-methyl- (9CI)
• BDBM50463197
• Histidine, 1-methyl-, L- (8CI)
• MFCD00005295
• AKOS016843072
• CS-W017722
• DB04151
• FD21681
• HY-W017006
• AS-57334
• 1-Methyl-L-histidine, >=98.0% (TLC)
• EN300-1168703
• J-019123
• Q27094989
• ABB55D30-E94C-412D-9B7A-E423FA8C1620
• InChI=1/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9683	96.83%
Caco-2	-	0.7030	70.30%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Lysosomes	0.5190	51.90%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.9574	95.74%
OATP1B3 inhibitior	+	0.9460	94.60%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8619	86.19%
P-glycoprotein inhibitior	-	0.9904	99.04%
P-glycoprotein substrate	-	0.9251	92.51%
CYP3A4 substrate	-	0.7258	72.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8415	84.15%
CYP3A4 inhibition	-	0.7751	77.51%
CYP2C9 inhibition	-	0.9430	94.30%
CYP2C19 inhibition	-	0.9482	94.82%
CYP2D6 inhibition	-	0.9362	93.62%
CYP1A2 inhibition	-	0.9510	95.10%
CYP2C8 inhibition	-	0.9622	96.22%
CYP inhibitory promiscuity	-	0.9800	98.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5639	56.39%
Eye corrosion	-	0.9685	96.85%
Eye irritation	-	0.9820	98.20%
Skin irritation	-	0.7124	71.24%
Skin corrosion	-	0.8649	86.49%
Ames mutagenesis	-	0.6937	69.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.8448	84.48%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.6854	68.54%
skin sensitisation	-	0.9094	90.94%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9112	91.12%
Acute Oral Toxicity (c)	III	0.5747	57.47%
Estrogen receptor binding	-	0.9482	94.82%
Androgen receptor binding	-	0.7524	75.24%
Thyroid receptor binding	-	0.7971	79.71%
Glucocorticoid receptor binding	-	0.6017	60.17%
Aromatase binding	-	0.8017	80.17%
PPAR gamma	+	0.5239	52.39%
Honey bee toxicity	-	0.9882	98.82%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	-	0.9411	94.11%

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	99.09%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.48%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	92.98%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.13%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.18%	86.33%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	87.32%	92.29%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.73%	99.17%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.11%	93.10%
CHEMBL4208	P20618	Proteasome component C5	81.83%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.57%	94.45%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.46%	90.24%

Plants that contains it

• Prunus domestica

Cross-Links

• PubChem: 92105
• LOTUS: LTS0111761
• wikiData: Q27094989