NP-MRD: Showing NP-Card for Thiamine hydrochloride (NP0047321)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 20:38:14 UTC

Updated at

2022-03-17 20:38:14 UTC

NP-MRD ID

NP0047321

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thiamine hydrochloride

Description

Thiamine hydrochloride was first documented in 2002 (PMID: 12224421).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306301800182D          

 20 19  0  0  0  0            999 V2000
   -1.8182   -0.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4918    2.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2635   -2.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0840   -2.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483    1.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3661    0.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3013   -0.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0336   -0.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7773    1.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7786   -1.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0628    0.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0628   -0.1753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0628    2.2997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7773    1.0622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3661   -0.1753    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -2.5690   -2.6935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0464   -1.4448    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8489    0.0000    0.0000 Cl  0  5  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.3435    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  8  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  3  1  0  0  0  0
 11  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13 12  2  0  0  0  0
 14  5  1  0  0  0  0
 14  9  2  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16  6  1  0  0  0  0
 16  7  2  0  0  0  0
 16  8  1  0  0  0  0
 17  4  1  0  0  0  0
 18  7  1  0  0  0  0
 18 11  1  0  0  0  0
M  CHG  2  16   1  19  -1
M  END
> <DATABASE_ID>
NP0047321

> <DATABASE_NAME>
NP-MRD

> <SMILES>
Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)NC1=N

> <INCHI_IDENTIFIER>
InChI=1S/C12H17N4OS.2ClH/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);2*1H/q+1;;/p-1

> <INCHI_KEY>
DPJRMOMPQZCRJU-UHFFFAOYSA-M

> <FORMULA>
C12H18Cl2N4OS

> <MOLECULAR_WEIGHT>
337.269

> <EXACT_MASS>
336.057837322

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.153758637463866

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium hydrochloride chloride

> <ALOGPS_LOGP>
-1.88

> <JCHEM_LOGP>
-3.0974126491384126

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.25564694993423

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.504603864011504

> <JCHEM_PKA_STRONGEST_BASIC>
5.5375484421713

> <JCHEM_POLAR_SURFACE_AREA>
75.91

> <JCHEM_REFRACTIVITY>
73.39970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thiamine hydrochloride chloride

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-JUN-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-18         0                                  
HETATM    1  C   UNK     0      -3.394  -0.757   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.651   4.293   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.359  -3.943   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.890  -3.782   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.650   3.523   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.683   1.213   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.562  -1.232   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.929  -1.232   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.318   3.523   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.650   1.983   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.453  -2.697   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.984   1.213   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.984  -0.327   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       1.984   4.293   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       3.318   1.983   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -0.683  -0.327   0.000  0.00  0.00           N+1
HETATM   17  O   UNK     0      -4.795  -5.028   0.000  0.00  0.00           O+0
HETATM   18  S   UNK     0       0.087  -2.697   0.000  0.00  0.00           S+0
HETATM   19 Cl   UNK     0       9.051   0.000   0.000  0.00  0.00          Cl-1
HETATM   20 Cl   UNK     0       0.000  -8.108   0.000  0.00  0.00          Cl+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    4   11                                                       
CONECT    4    3   17                                                       
CONECT    5   10   14                                                       
CONECT    6   10   16                                                       
CONECT    7   16   18                                                       
CONECT    8    1   11   16                                                  
CONECT    9    2   14   15                                                  
CONECT   10    5    6   12                                                  
CONECT   11    3    8   18                                                  
CONECT   12   10   13   15                                                  
CONECT   13   12                                                            
CONECT   14    5    9                                                       
CONECT   15    9   12                                                       
CONECT   16    6    7    8                                                  
CONECT   17    4                                                            
CONECT   18    7   11                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
Thiamine chloride hydrochloride	ChEBI
Thiamine dichloride	ChEBI
Thiamine HCL	ChEBI
Thiamine(2+) dichloride	ChEBI
Thiaminium chloride hydrochloride	ChEBI
Thiamin	MeSH
Vitamin b 1	MeSH
Aneurin	MeSH
Thiamine mononitrate	MeSH
Mononitrate, thiamine	MeSH
Vitamin b1	MeSH
Thiamine	MeSH
Thiamine hydrochloride	ChEBI

Chemical Formula

C₁₂H₁₈Cl₂N₄OS

Average Mass

337.2690 Da

Monoisotopic Mass

336.05784 Da

IUPAC Name

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium hydrochloride chloride

Traditional Name

thiamine hydrochloride chloride

CAS Registry Number

67-03-8

SMILES

Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)NC1=N

InChI Identifier

InChI=1S/C12H17N4OS.2ClH/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);2*1H/q+1;;/p-1

InChI Key

DPJRMOMPQZCRJU-UHFFFAOYSA-M

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bos taurus	FooDB	DTU Food
Capsicum annuum	FooDB	DTU Food
Coffea arabica L.	FooDB	DTU Food
Coffea canephora	FooDB	DTU Food
Cucurbita maxima	FooDB	DTU Food
Phaseolus vulgaris	FooDB	DTU Food

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiamines. Thiamines are compounds containing a thiamine moiety, which is structurally characterized by a 3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl backbone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Thiamines

Alternative Parents

Substituents

Thiamine
4,5-disubstituted 1,3-thiazole
Aminopyrimidine
Imidolactam
Azole
Thiazole
Heteroaromatic compound
Azacycle
Hydrochloride
Hydrocarbon derivative
Organic salt
Alcohol
Organopnictogen compound
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Organic chloride salt
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

thiamine (CHEBI:49105 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.9	ALOGPS
logP	-3.1	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	15.5	ChemAxon
pKa (Strongest Basic)	5.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.4 m³·mol⁻¹	ChemAxon
Polarizability	28.15 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DBSALT000205

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008416

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thiamine

METLIN ID

Not Available

PubChem Compound

6202

PDB ID

Not Available

ChEBI ID

49105

Good Scents ID

Not Available

References

General References

Yazici S, Velioglu YS: Effect of thiamine hydrochloride, pyridoxine hydrochloride and calcium-d-pantothenate on the patulin content of apple juice concentrate. Nahrung. 2002 Aug;46(4):256-7. doi: 10.1002/1521-3803(20020701)46:4<256::AID-FOOD256>3.0.CO;2-A. [PubMed:12224421 ]
Juveriya Fathima S, Fathima I, Abhishek V, Khanum F: Phosphatidylcholine, an edible carrier for nanoencapsulation of unstable thiamine. Food Chem. 2016 Apr 15;197(Pt A):562-70. doi: 10.1016/j.foodchem.2015.11.005. Epub 2015 Nov 2. [PubMed:26616989 ]
Alemanno F, Ghisi D, Westermann B, Bettoni A, Fanelli A, La Colla L, Danelli G, Cesana BM: The use of vitamin B1 as a perineural adjuvant to middle interscalene block for postoperative analgesia after shoulder surgery. Acta Biomed. 2016 May 6;87(1):22-7. [PubMed:27163892 ]

Showing NP-Card for Thiamine hydrochloride (NP0047321)

MOL for NP0047321 (Thiamine hydrochloride)

3D MOL for NP0047321 (Thiamine hydrochloride)

3D SDF for NP0047321 (Thiamine hydrochloride)

3D-SDF for NP0047321 (Thiamine hydrochloride)

PDB for NP0047321 (Thiamine hydrochloride)

3D PDB for NP0047321 (Thiamine hydrochloride)

SMILES for NP0047321 (Thiamine hydrochloride)

INCHI for NP0047321 (Thiamine hydrochloride)

Structure for NP0047321 (Thiamine hydrochloride)

3D Structure for NP0047321 (Thiamine hydrochloride)