NP-MRD: Showing NP-Card for Thiamine mononitrate (NP0336852)

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Record Information

Version

2.0

Created at

2024-09-11 08:07:50 UTC

Updated at

2024-09-11 08:07:50 UTC

NP-MRD ID

NP0336852

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thiamine mononitrate

Description

Thiamine mononitrate 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. Thiamine mononitrate is a drug. Thiamine mononitrate is a very strong basic compound (based on its pKa). Thiamine mononitrate is a synthetic form of vitamin B1.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241215232D          

 22 22  0  0  0  0            999 V2000
   -2.5856    0.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5035    1.7238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3703    0.4924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9290    0.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0110   -0.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545   -0.9029    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.5343   -0.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419   -1.3134    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0110   -2.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545   -1.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5343   -1.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2881   -2.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5327   -2.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1073   -2.3804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081    1.6416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7648    2.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7648    2.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9432   -0.2471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7640   -0.2471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7640   -1.0671    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.5856   -0.2471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2 17  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 16  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
M  CHG  2   7   1  21  -1
M  END
> <DATABASE_ID>
NP0336852

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[O-]N(=O)=O.CC1=C(CCO)SC=[N+]1CC1=C(N)N=C(C)N=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H17N4OS.NO3/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13;2-1(3)4/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15);/q+1;-1

> <INCHI_KEY>
UIERGBJEBXXIGO-UHFFFAOYSA-N

> <FORMULA>
C12H17N5O4S

> <MOLECULAR_WEIGHT>
327.359

> <EXACT_MASS>
327.100124747

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.15375863746388

> <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 nitrate

> <ALOGPS_LOGP>
0.01

> <JCHEM_LOGP>
-3.0974126491384126

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.255646949944182

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.504603864004356

> <JCHEM_PKA_STRONGEST_BASIC>
5.537548442171222

> <JCHEM_POLAR_SURFACE_AREA>
75.91

> <JCHEM_REFRACTIVITY>
73.39970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thiamine nitrate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.827   1.685   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -4.673   3.218   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      -0.691   0.919   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.222   1.532   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.601   0.766   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.754  -0.766   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.528  -1.685   0.000  0.00  0.00           N+1
HETATM    8  C   UNK     0      -0.997  -1.226   0.000  0.00  0.00           C+0
HETATM    9  S   UNK     0      -0.078  -2.452   0.000  0.00  0.00           S+0
HETATM   10  C   UNK     0      -3.754  -4.137   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.528  -3.218   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.997  -3.677   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.538  -5.210   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.994  -5.516   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.067  -4.443   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      -2.068   3.064   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -3.294   3.984   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.294   5.516   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.761  -0.461   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       3.293  -0.461   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       3.293  -1.992   0.000  0.00  0.00           O-1
HETATM   22  O   UNK     0       4.827  -0.461   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1   17                                                       
CONECT    3    4                                                            
CONECT    4    3    5   16                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   12                                                       
CONECT   10   11                                                            
CONECT   11    7   10   12                                                  
CONECT   12    9   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    4   17                                                       
CONECT   17    2   16   18                                                  
CONECT   18   17                                                            
CONECT   19   20                                                            
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
Thiamine mononitric acid	Generator
VITAMIN b1 mononitrATE	ChEMBL
THIAMINE nitrATE	ChEMBL
VITAMIN b1 mononitric acid	Generator
THIAMINE nitric acid	Generator
Aneurin	MeSH
Mononitrate, thiamine	MeSH
Thiamine	MeSH
Vitamin b 1	MeSH
Thiamin	MeSH
Vitamin b1	MeSH

Chemical Formula

C₁₂H₁₇N₅O₄S

Average Mass

327.3590 Da

Monoisotopic Mass

327.10012 Da

IUPAC Name

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

Traditional Name

thiamine nitrate

CAS Registry Number

Not Available

SMILES

[O-]N(=O)=O.CC1=C(CCO)SC=[N+]1CC1=C(N)N=C(C)N=C1

InChI Identifier

InChI=1S/C12H17N4OS.NO3/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13;2-1(3)4/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15);/q+1;-1

InChI Key

UIERGBJEBXXIGO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Organic nitrate
Thiazole
Heteroaromatic compound
Organic nitro compound
Organic nitric acid
Organic nitric acid or derivatives
Azacycle
Organic 1,3-dipolar compound
Allyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Amine
Alcohol
Organic nitrogen compound
Organic salt
Organic oxide
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	0.01	ALOGPS
logP	-3.1	ChemAxon
logS	-4.1	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

HMDB0031755

DrugBank ID

DBSALT001495

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008426

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

10762

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Thiamine mononitrate (NP0336852)

MOL for NP0336852 (Thiamine mononitrate)

3D MOL for NP0336852 (Thiamine mononitrate)

3D SDF for NP0336852 (Thiamine mononitrate)

3D-SDF for NP0336852 (Thiamine mononitrate)

PDB for NP0336852 (Thiamine mononitrate)

3D PDB for NP0336852 (Thiamine mononitrate)

SMILES for NP0336852 (Thiamine mononitrate)

INCHI for NP0336852 (Thiamine mononitrate)

Structure for NP0336852 (Thiamine mononitrate)

3D Structure for NP0336852 (Thiamine mononitrate)