3-(4-Amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium

Details

• Internal ID: bb690f5c-c12a-4e62-9925-a2b0015b72df
• Taxonomy: Organoheterocyclic compounds > Diazines > Pyrimidines and pyrimidine derivatives > Thiamines
• IUPAC Name: 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol
• SMILES (Canonical): CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO
• SMILES (Isomeric): CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO
• InChI: InChI=1S/C12H17N4OS/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q+1
• InChI Key: JZRWCGZRTZMZEH-UHFFFAOYSA-N
• Popularity: 13,361 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₇N₄OS+
• Molecular Weight: 265.36 g/mol
• Exact Mass: 265.11230735 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.61
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• vitamin B1
• thiamin
• Aneurin
• Antiberiberi factor
• Thiadoxine
• Betaxin
• Biamine
• Thiamine ion
• 70-16-6
• Vitaneuron
• Bequin
• thiaminium
• Bewon
• thiamine(1+)
• thiamine(1+) ion
• Betabion
• [3H]thiamine
• [3H]-thiamine
• [3H]vitamin B1
• Thiamine (Vit B1)
• 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol
• Vitamin B 1
• Thiamine hydrochloride [JAN]
• 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium
• 4ABT0J945J
• Thiamine monohydrochloride
• CHEBI:18385
• 3-(4-AMINO-2-METHYL-PYRIMIDIN-5-YLMETHYL)-5-(2-HYDROXY-ETHYL)-4-METHYL-THIAZOL-3-IUM
• Chloride-hydrochloride salt of thiamine
• THD
• VIB
• Vitamin B1 hydrochloride (VAN)
• Thiamine, chloride, hydrochloride
• Vitamin B1 (TN)
• vitamin b1(thiamine)
• UNII-4ABT0J945J
• 3-((4-Amino-2-methylpyrimidin-5-yl)methyl)-5-(2-hydroxyethyl)-4-methylthiazol-3-ium
• 3[(4-Amino-2-methyl-5-pyrimidinyl)-methyl]-5-(2-hydroxyethyl)-4-methylthiazolium chloride
• Thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-methyl-
• NSC36226
• Thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-methyl-, chloride, monohydrochloride
• THIAMIN, VITAMIN B1
• 1sbr
• 3rlb
• ThOH
• 3-((4-Amino-2-methyl-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-m- ethylthiazolium chloride, monohydrochloride
• 3-((4-Amino-2-methyl-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-m-ethylthiazolium chloride, monohydrochloride
• Prestwick0_000631
• Prestwick1_000631
• Prestwick2_000631
• Prestwick3_000631
• Thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-m- ethyl, chloride, monohydrochloride
• Thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-m-ethyl, chloride, monohydrochloride
• Thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-methyl-chloride (1:1)
• bmse000274
• D06PQT
• D07TYL
• TimTec1_000613
• CHEMBL1547
• THIAMIN; VITAMIN B1
• SCHEMBL10075
• BSPBio_000622
• SPBio_002841
• BPBio1_000686
• C12H17N4OS
• GTPL4628
• GTPL4629
• SCHEMBL22129283
• DTXSID50220251
• JZRWCGZRTZMZEH-UHFFFAOYSA-N
• BDBM50373877
• STL301841
• AKOS000668650
• DB00152
• LS-2340
• 2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-3-ium-5-yl]ethanol
• SMP1_000084
• NCGC00017013-06
• NCGC00188957-01
• NCGC00188957-02
• LT00233141
• C00378
• Q83187
• 3-(2-Methyl-4-aminopyrimidine-5-ylmethyl)-4-methylthiazolium-5-ethanol
• [5-[[5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium-3-yl]methyl]-2-methylpyrimidin-4-yl]azanium dichloride
• 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol chloride

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9028	90.28%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Lysosomes	0.6134	61.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9044	90.44%
OATP1B3 inhibitior	+	0.9390	93.90%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.8503	85.03%
P-glycoprotein inhibitior	-	0.9243	92.43%
P-glycoprotein substrate	-	0.7050	70.50%
CYP3A4 substrate	-	0.5233	52.33%
CYP2C9 substrate	-	0.7872	78.72%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.8019	80.19%
CYP2C9 inhibition	-	0.7521	75.21%
CYP2C19 inhibition	-	0.7397	73.97%
CYP2D6 inhibition	-	0.7523	75.23%
CYP1A2 inhibition	-	0.5800	58.00%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.7795	77.95%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4896	48.96%
Eye corrosion	-	0.9772	97.72%
Eye irritation	-	0.9520	95.20%
Skin irritation	-	0.7457	74.57%
Skin corrosion	-	0.9013	90.13%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4234	42.34%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.7718	77.18%
skin sensitisation	-	0.8541	85.41%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.5765	57.65%
Acute Oral Toxicity (c)	III	0.6171	61.71%
Estrogen receptor binding	-	0.6363	63.63%
Androgen receptor binding	-	0.5428	54.28%
Thyroid receptor binding	+	0.6272	62.72%
Glucocorticoid receptor binding	-	0.4685	46.85%
Aromatase binding	-	0.5319	53.19%
PPAR gamma	+	0.5342	53.42%
Honey bee toxicity	-	0.9077	90.77%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	-	0.5053	50.53%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	12500 nM	IC50	DOI: 10.1007/s00044-011-9557-9

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.77%	96.09%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	88.65%	93.10%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.28%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	87.25%	94.73%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.99%	89.34%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.73%	95.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.51%	97.36%
CHEMBL3492	P49721	Proteasome Macropain subunit	83.21%	90.24%
CHEMBL230	P35354	Cyclooxygenase-2	81.96%	89.63%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.23%	99.17%
CHEMBL235	P37231	Peroxisome proliferator-activated receptor gamma	81.21%	95.39%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.01%	85.14%

Plants that contains it

• Aconitum leucostomum
• Aiouea montana
• Alhagi maurorum
• Alstonia muelleriana
• Aquilegia ecalcarata
• Artemisia szowitziana
• Blumea axillaris
• Ceanothus velutinus
• Changium smyrnioides
• Chlorophytum borivilianum
• Coreopsis nodosa
• Croton megistocarpus
• Dacrydium cupressinum
• Dipterocarpus dyeri
• Euphorbia lancifolia
• Fragaria vesca
• Gamblea innovans
• Garcinia scortechinii
• Gardenia tubifera
• Geranium sibiricum
• Glycine tomentella
• Hippophae rhamnoides
• Ipomoea cairica
• Isodon lophanthoides
• Kopsia grandifolia
• Lagerstroemia indica
• Lasianthus fordii
• Ledebouria socialis
• Lycopus europaeus
• Machilus japonica
• Nicotiana undulata
• Oryza sativa
• Passiflora incarnata
• Perilla frutescens
• Persea barbujana
• Phaseolus vulgaris
• Senecio isatideus
• Senecio paludaffinis
• Seriphidium cinum
• Solanum tuberosum
• Spinacia oleracea
• Strobilanthes cusia
• Theobroma cacao
• Trigonella foenum-graecum
• Trigonella grandiflora
• Tripolium pannonicum
• Uvaria calamistrata

Cross-Links

• PubChem: 1130
• NPASS: NPC150950
• ChEMBL: CHEMBL1547
• LOTUS: LTS0030620
• wikiData: Q83187