NP-MRD: Showing NP-Card for 2-Methyl-1-hydroxypropyl-ThPP (NP0087657)

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Record Information

Version

2.0

Created at

2022-05-11 16:55:59 UTC

Updated at

2022-05-11 16:55:59 UTC

NP-MRD ID

NP0087657

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Methyl-1-hydroxypropyl-ThPP

Description

2-Methyl-1-hydroxypropyl-ThPP belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group. 2-Methyl-1-hydroxypropyl-ThPP is a very strong basic compound (based on its pKa). 2-Methyl-1-hydroxypropyl-ThPP exists in all living organisms, ranging from bacteria to humans. 2-Methyl-1-hydroxypropyl-ThPP is found in Apis cerana. In humans, 2-methyl-1-hydroxypropyl-THPP is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway.

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv0541 02231220542D          
 
 31 32  0  0  0  0            999 V2000
   18.9913  -13.6159    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   19.3704  -12.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5736  -14.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2744  -13.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1836  -13.0162    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.9981  -12.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3077  -13.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4805  -15.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5611  -13.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1781  -12.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4530  -11.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0417  -14.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5611  -14.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -13.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7344  -13.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -14.8738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2744  -14.8634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1275  -13.6194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4684  -14.1397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1275  -14.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1611  -13.6917    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.4141  -14.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8950  -14.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4127  -14.5187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5878  -13.6227    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.3184  -13.9985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8394  -14.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1611  -12.8659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5878  -12.7969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8059  -11.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7248  -12.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  5  7  1  0  0  0  0
 18 20  1  0  0  0  0
 21 28  2  0  0  0  0
 25 29  2  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
M  CHG  1   1   1
M  END

     RDKit          3D

 58 59  0  0  0  0  0  0  0  0999 V2000
   -3.0404    5.4598    2.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0255    4.0907    1.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0563    3.2031    2.3150 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0722    1.9503    1.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9067    1.5933    0.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9903    0.4014   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7072   -0.2864   -0.3391 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.6554   -1.6177   -0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7982   -2.6000   -0.0869 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6887   -2.2359   -1.1575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3182   -3.9697   -0.4115 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4408   -4.5369    0.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5474   -4.0257   -1.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0441   -1.9694   -0.3207 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5443   -0.4318   -0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9194    0.1196   -0.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9580   -0.9381   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2028   -0.2517   -0.8650 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0490   -0.3235    0.6088 P   0  0  1  0  0  5  0  0  0  0  0  0
    4.8083    1.1488    1.2095 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3567   -1.4134    1.6447 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6829   -0.4322    0.4772 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3079    0.5587   -0.7385 P   0  0  2  0  0  5  0  0  0  0  0  0
    6.7025    0.2112   -2.0822 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9603    0.2088   -0.8134 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1301    2.1798   -0.4451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5945    0.3204   -0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4532    1.8343   -0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8328    2.5959    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7585    2.3239   -0.7663 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8454    3.7741    0.9041 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9844    5.9550    2.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2206    6.0716    2.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569    5.4484    3.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029    1.2579    2.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5520    0.4436   -0.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6497   -0.2995    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3274   -2.5512    0.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2226   -1.8943   -1.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1686   -4.6455   -0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850   -5.6699    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4009   -4.2709    0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9154   -4.2012    1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6805   -3.0641   -2.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4981   -4.2950   -1.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9588   -4.8302   -2.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0981    0.8604    0.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1065    0.6240   -1.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9772   -1.7643   -1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9589   -1.4005    0.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9181   -1.6929    2.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1687   -0.6206   -0.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2628    2.5144   -0.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0762    2.3173    0.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3275    1.9902   -1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3407    2.3147   -1.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7172    2.0328   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3587    2.4281   -1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  1  0
 11  9  1  0
  9 10  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5 29  2  0
 29 30  1  0
 29 31  1  0
 31  2  2  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
  7 27  1  0
 27 28  1  0
 27 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 19 18  1  6
 19 21  1  0
 19 20  2  0
 19 22  1  0
 23 22  1  1
 23 25  1  0
 23 26  1  0
 23 24  2  0
 15 14  1  0
 14  8  1  0
  4  5  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
 11 40  1  6
 13 44  1  0
 13 45  1  0
 13 46  1  0
  9 38  1  1
 10 39  1  0
  6 36  1  0
  6 37  1  0
 30 57  1  0
 30 58  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 21 51  1  0
 25 52  1  0
 26 53  1  0
M  CHG  1   7   1
M  END

 
  Mrv0541 02231220542D          
 
 31 32  0  0  0  0            999 V2000
   18.9913  -13.6159    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   19.3704  -12.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5736  -14.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2744  -13.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1836  -13.0162    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.9981  -12.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3077  -13.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4805  -15.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5611  -13.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1781  -12.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4530  -11.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0417  -14.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5611  -14.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -13.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7344  -13.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -14.8738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2744  -14.8634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1275  -13.6194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4684  -14.1397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1275  -14.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1611  -13.6917    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.4141  -14.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8950  -14.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4127  -14.5187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5878  -13.6227    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.3184  -13.9985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8394  -14.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1611  -12.8659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5878  -12.7969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8059  -11.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7248  -12.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  5  7  1  0  0  0  0
 18 20  1  0  0  0  0
 21 28  2  0  0  0  0
 25 29  2  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
M  CHG  1   1   1
M  END
> <DATABASE_ID>
NP0087657

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(O)C1=[N+](CC2=C(N)N=C(C)N=C2)C(C)=C(CCOP(O)(=O)OP(O)(O)=O)S1

> <INCHI_IDENTIFIER>
InChI=1S/C16H26N4O8P2S/c1-9(2)14(21)16-20(8-12-7-18-11(4)19-15(12)17)10(3)13(31-16)5-6-27-30(25,26)28-29(22,23)24/h7,9,14,21H,5-6,8H2,1-4H3,(H4-,17,18,19,22,23,24,25,26)/p+1

> <INCHI_KEY>
SSYCSHKTIOHFEZ-UHFFFAOYSA-O

> <FORMULA>
C16H27N4O8P2S

> <MOLECULAR_WEIGHT>
497.42

> <EXACT_MASS>
497.102482574

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
46.15230293114812

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-(1-hydroxy-2-methylpropyl)-4-methyl-1,3-thiazol-3-ium

> <ALOGPS_LOGP>
-0.43

> <JCHEM_LOGP>
-6.04769278226597

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.1978436606439984

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7783050504179663

> <JCHEM_PKA_STRONGEST_BASIC>
5.531111660504906

> <JCHEM_POLAR_SURFACE_AREA>
189.2

> <JCHEM_REFRACTIVITY>
125.57509999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-(1-hydroxy-2-methylpropyl)-4-methyl-1,3-thiazol-3-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      35.450 -25.416   0.000  0.00  0.00           N+1
HETATM    2  C   UNK     0      36.158 -24.046   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      36.537 -26.510   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      34.112 -24.651   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0      37.676 -24.297   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0      35.463 -22.670   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      37.908 -25.815   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      36.364 -28.035   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.781 -25.423   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.932 -22.580   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      36.312 -21.383   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      39.278 -26.523   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.781 -26.973   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.430 -24.657   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      40.571 -25.687   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      31.430 -27.764   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      34.112 -27.745   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      30.105 -25.423   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      41.941 -26.394   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      30.105 -26.973   0.000  0.00  0.00           C+0
HETATM   21  P   UNK     0      43.234 -25.558   0.000  0.00  0.00           P+0
HETATM   22  C   UNK     0      28.773 -27.745   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      44.604 -26.265   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      43.704 -27.102   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      45.897 -25.429   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0      47.261 -26.131   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      46.367 -26.973   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      43.234 -24.016   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      45.897 -23.888   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      33.238 -21.195   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      33.086 -23.865   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2    7                                                       
CONECT    6    2   10   11                                                  
CONECT    7    3   12    5                                                  
CONECT    8    3                                                            
CONECT    9    4   13   14                                                  
CONECT   10    6   30   31                                                  
CONECT   11    6                                                            
CONECT   12    7   15                                                       
CONECT   13    9   16   17                                                  
CONECT   14    9   18                                                       
CONECT   15   12   19                                                       
CONECT   16   13   20                                                       
CONECT   17   13                                                            
CONECT   18   14   20                                                       
CONECT   19   15   21                                                       
CONECT   20   16   22   18                                                  
CONECT   21   19   23   24   28                                             
CONECT   22   20                                                            
CONECT   23   21   25                                                       
CONECT   24   21                                                            
CONECT   25   23   26   27   29                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   21                                                            
CONECT   29   25                                                            
CONECT   30   10                                                            
CONECT   31   10                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
1-Hydroxy-2-methylpropyl-thiamine diphosphate	ChEBI
1-Hydroxy-2-methylpropyl-thiamine pyrophosphate	ChEBI
2-Methyl-1-hydroxypropyl-thiamine diphosphate	ChEBI
2-Methyl-1-hydroxypropyl-thiamine pyrophosphate	ChEBI
2-Methyl-1-hydroxypropyl-TPP	ChEBI
3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-5-(2-diphosphoethyl)-2-(1-hydroxy-2-methylpropyl)-4-methyl-1,3-thiazol-3-ium	ChEBI
1-Hydroxy-2-methylpropyl-thiamine diphosphoric acid	Generator
1-Hydroxy-2-methylpropyl-thiamine pyrophosphoric acid	Generator
2-Methyl-1-hydroxypropyl-thiamine diphosphoric acid	Generator
2-Methyl-1-hydroxypropyl-thiamine pyrophosphoric acid	Generator
2-Methyl-1-hydroxypropyl-THPP	ChEBI

Chemical Formula

C₁₆H₂₇N₄O₈P₂S

Average Mass

497.4200 Da

Monoisotopic Mass

497.10248 Da

IUPAC Name

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-(1-hydroxy-2-methylpropyl)-4-methyl-1,3-thiazol-3-ium

Traditional Name

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-(1-hydroxy-2-methylpropyl)-4-methyl-1,3-thiazol-3-ium

CAS Registry Number

Not Available

SMILES

CC(C)C(O)C1=[N+](CC2=C(N)N=C(C)N=C2)C(C)=C(CCOP(O)(=O)OP(O)(O)=O)S1

InChI Identifier

InChI=1S/C16H26N4O8P2S/c1-9(2)14(21)16-20(8-12-7-18-11(4)19-15(12)17)10(3)13(31-16)5-6-27-30(25,26)28-29(22,23)24/h7,9,14,21H,5-6,8H2,1-4H3,(H4-,17,18,19,22,23,24,25,26)/p+1

InChI Key

SSYCSHKTIOHFEZ-UHFFFAOYSA-O

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Apis cerana	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Thiamine phosphates

Alternative Parents

Substituents

Thiamine-phosphate
Organic pyrophosphate
2,4,5-trisubstituted 1,3-thiazole
Aminopyrimidine
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Imidolactam
Heteroaromatic compound
Azole
Thiazole
Secondary alcohol
Azacycle
Hydrocarbon derivative
Amine
Organic oxide
Primary amine
Alcohol
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Aromatic alcohol
Organic oxygen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

thiamine phosphate (CHEBI:48522 )
aminopyrimidine (CHEBI:48522 )
1,3-thiazolium cation (CHEBI:48522 )

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	-0.43	ALOGPS
logP	-6	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	5.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.2 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	125.58 m³·mol⁻¹	ChemAxon
Polarizability	46.15 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

HMDB0006866

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB024122

KNApSAcK ID

Not Available

Chemspider ID

26333171

KEGG Compound ID

C15976

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23724626

PDB ID

Not Available

ChEBI ID

48522

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Methyl-1-hydroxypropyl-ThPP (NP0087657)

MOL for NP0087657 (2-Methyl-1-hydroxypropyl-ThPP)

3D MOL for NP0087657 (2-Methyl-1-hydroxypropyl-ThPP)

3D SDF for NP0087657 (2-Methyl-1-hydroxypropyl-ThPP)

3D-SDF for NP0087657 (2-Methyl-1-hydroxypropyl-ThPP)

PDB for NP0087657 (2-Methyl-1-hydroxypropyl-ThPP)

3D PDB for NP0087657 (2-Methyl-1-hydroxypropyl-ThPP)

SMILES for NP0087657 (2-Methyl-1-hydroxypropyl-ThPP)

INCHI for NP0087657 (2-Methyl-1-hydroxypropyl-ThPP)

Structure for NP0087657 (2-Methyl-1-hydroxypropyl-ThPP)

3D Structure for NP0087657 (2-Methyl-1-hydroxypropyl-ThPP)