MiMeDB: Showing metabocard for 2-Methyl-1-hydroxybutyl-ThPP (MMDBc0049903)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:45:53 UTC

Update Date

2025-01-15 23:47:48 UTC

Metabolite ID

MMDBc0049903

Metabolite Identification

Common Name

2-Methyl-1-hydroxybutyl-ThPP

Description

2-Methyl-1-hydroxybutyl-ThPP is an intermediate in Valine, leucine and isoleucine degradation. 2-Methyl-1-hydroxybutyl-ThPP is the second to last step for the synthesis of (S)-2-Methylbutanoyl-CoA. 2-Methyl-1-hydroxybutyl-ThPP is converted from (S)-3-Methyl-2-oxopentanoic acid via the enzyme 2-oxoisovalerate dehydrogenase E1 component, alpha subunit(EC 1.2.4.4). It is then converted to S-(2-Methylbutanoyl)-dihydrolipoamide-E via the same enzyme.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241203552D          

 32 33  0  0  1  0            999 V2000
    5.4878   -3.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4878   -4.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7733   -3.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7733   -5.1806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0588   -3.9430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0588   -4.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3443   -5.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2023   -3.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7251   -4.9321    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167   -3.9430    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.2225   -4.2206    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8100   -4.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6704   -3.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0029   -4.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8272   -4.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1455   -5.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9660   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3016   -6.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1220   -6.6149    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.9425   -6.7011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2083   -5.7944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0358   -7.4354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2781   -7.4548    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.5244   -7.7904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0318   -7.1193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6136   -8.2085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8419   -2.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6265   -2.5456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2289   -2.2484    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4004   -1.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4442   -2.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7873   -0.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  2  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  8  1  0  0  0  0
  2  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 10  2  0  0  0  0
 10 14  1  0  0  0  0
 14 12  2  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 23 26  1  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  1  0  0  0
 30 32  1  0  0  0  0
M  CHG  1  10   1
M  END

HMDB0012310
     RDKit          3D
2-Methyl-1-hydroxybutyl-ThPP
 61 62  0  0  0  0  0  0  0  0999 V2000
   -3.6807   -4.9158    0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6852   -3.8166   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896   -2.5701   -0.4054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5947   -2.7281   -1.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6572   -1.3600   -0.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1270   -1.7228   -2.1039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889   -1.1502    0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1252   -2.1927    0.2616 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533   -1.3429    1.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9309   -1.7158    2.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1041   -0.9050    1.7407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3803   -0.9906    0.3735 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7320   -0.0355    0.0094 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.8348    1.0378    1.0971 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1445   -0.9914    0.0208 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5449    0.7511   -1.4730 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9716    1.5357   -1.8696 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.7264    2.9721   -2.2938 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9928    1.5221   -0.5324 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7104    0.6741   -3.1219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802   -0.2811    1.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1968    0.7192    2.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619   -0.1952    0.9647 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.2325    0.9131    1.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8123    2.1908    0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4703    3.2139    1.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0960    4.4321    1.0611 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0338    4.7224   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6121    6.0931   -0.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3538    3.7690   -1.1300 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7405    2.5119   -0.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0322    1.6340   -1.7948 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3549   -4.5356    0.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2662   -5.1711   -0.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1286   -5.8016    0.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1144   -4.1082   -1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0298   -3.6759    0.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9181   -2.2904    0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3625   -3.4301   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1156   -3.0505   -2.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0308   -1.7282   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3066   -0.4858   -0.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1953   -2.0670   -2.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1531   -2.7794    1.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -1.6030    3.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9933   -1.3164    2.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0397    0.1629    2.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9137   -1.8633   -0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2245    2.4247   -0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3912    0.0811   -2.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8923    0.2643    3.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7078    1.5497    2.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6847    1.0300    3.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4059    0.9882    2.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2267    0.6148    0.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4960    3.0804    2.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2766    6.8581   -0.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6324    6.1727   -1.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4164    6.3011   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3223    0.9613   -2.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632    1.6387   -2.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 17 20  1  0
  9 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 23  7  2  0
 31 25  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  1
  4 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  6 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 15 48  1  0
 19 49  1  0
 20 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 26 56  1  0
 29 57  1  0
 29 58  1  0
 29 59  1  0
 32 60  1  0
 32 61  1  0
M  CHG  1  23   1
M  END


  Mrv0541 02241203552D          

 32 33  0  0  1  0            999 V2000
    5.4878   -3.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4878   -4.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7733   -3.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7733   -5.1806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0588   -3.9430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0588   -4.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3443   -5.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2023   -3.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7251   -4.9321    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167   -3.9430    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.2225   -4.2206    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8100   -4.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6704   -3.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0029   -4.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8272   -4.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1455   -5.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9660   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3016   -6.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1220   -6.6149    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.9425   -6.7011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2083   -5.7944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0358   -7.4354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2781   -7.4548    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.5244   -7.7904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0318   -7.1193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6136   -8.2085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8419   -2.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6265   -2.5456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2289   -2.2484    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4004   -1.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4442   -2.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7873   -0.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  2  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  8  1  0  0  0  0
  2  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 10  2  0  0  0  0
 10 14  1  0  0  0  0
 14 12  2  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 23 26  1  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  1  0  0  0
 30 32  1  0  0  0  0
M  CHG  1  10   1
M  END
> <DATABASE_ID>
MMDBc0049903

> <DATABASE_NAME>
MIME

> <SMILES>
CC[C@H](C)C(O)C1=[N+](CC2=CN=C(C)N=C2N)C(C)=C(CCOP(O)(=O)OP(O)(O)=O)S1

> <INCHI_IDENTIFIER>
InChI=1S/C17H28N4O8P2S/c1-5-10(2)15(22)17-21(9-13-8-19-12(4)20-16(13)18)11(3)14(32-17)6-7-28-31(26,27)29-30(23,24)25/h8,10,15,22H,5-7,9H2,1-4H3,(H4-,18,19,20,23,24,25,26,27)/p+1/t10-,15?/m0/s1

> <INCHI_KEY>
CUBSXOWPMAOFDG-MYHCZTBNSA-O

> <FORMULA>
C17H29N4O8P2S

> <MOLECULAR_WEIGHT>
511.447

> <EXACT_MASS>
511.118132638

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
48.10778367141567

> <JCHEM_BIOAVAILABILITY>
0

> <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-[(2S)-1-hydroxy-2-methylbutyl]-4-methyl-1,3-thiazol-3-ium

> <ALOGPS_LOGP>
-0.18

> <JCHEM_LOGP>
-5.603848042497346

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.1978436598281634

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7783050503632278

> <JCHEM_PKA_STRONGEST_BASIC>
5.531111480062937

> <JCHEM_POLAR_SURFACE_AREA>
189.2

> <JCHEM_REFRACTIVITY>
130.17609999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.42e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012310
     RDKit          3D
2-Methyl-1-hydroxybutyl-ThPP
 61 62  0  0  0  0  0  0  0  0999 V2000
   -3.6807   -4.9158    0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6852   -3.8166   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896   -2.5701   -0.4054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5947   -2.7281   -1.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6572   -1.3600   -0.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1270   -1.7228   -2.1039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889   -1.1502    0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1252   -2.1927    0.2616 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533   -1.3429    1.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9309   -1.7158    2.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1041   -0.9050    1.7407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3803   -0.9906    0.3735 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7320   -0.0355    0.0094 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.8348    1.0378    1.0971 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1445   -0.9914    0.0208 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5449    0.7511   -1.4730 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9716    1.5357   -1.8696 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.7264    2.9721   -2.2938 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9928    1.5221   -0.5324 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7104    0.6741   -3.1219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802   -0.2811    1.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1968    0.7192    2.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619   -0.1952    0.9647 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.2325    0.9131    1.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8123    2.1908    0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4703    3.2139    1.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0960    4.4321    1.0611 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0338    4.7224   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6121    6.0931   -0.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3538    3.7690   -1.1300 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7405    2.5119   -0.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0322    1.6340   -1.7948 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3549   -4.5356    0.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2662   -5.1711   -0.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1286   -5.8016    0.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1144   -4.1082   -1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0298   -3.6759    0.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9181   -2.2904    0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3625   -3.4301   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1156   -3.0505   -2.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0308   -1.7282   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3066   -0.4858   -0.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1953   -2.0670   -2.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1531   -2.7794    1.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -1.6030    3.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9933   -1.3164    2.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0397    0.1629    2.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9137   -1.8633   -0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2245    2.4247   -0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3912    0.0811   -2.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8923    0.2643    3.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7078    1.5497    2.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6847    1.0300    3.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4059    0.9882    2.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2267    0.6148    0.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4960    3.0804    2.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2766    6.8581   -0.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6324    6.1727   -1.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4164    6.3011   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3223    0.9613   -2.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632    1.6387   -2.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 17 20  1  0
  9 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 23  7  2  0
 31 25  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  1
  4 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  6 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 15 48  1  0
 19 49  1  0
 20 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 26 56  1  0
 29 57  1  0
 29 58  1  0
 29 59  1  0
 32 60  1  0
 32 61  1  0
M  CHG  1  23   1
M  END

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      10.244  -7.360   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.244  -8.900   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.910  -6.590   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       8.910  -9.670   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.576  -7.360   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.576  -8.900   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.243  -9.670   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.578  -6.590   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      10.687  -9.207   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      12.911  -7.360   0.000  0.00  0.00           N+1
HETATM   11  S   UNK     0      15.349  -7.878   0.000  0.00  0.00           S+0
HETATM   12  C   UNK     0      14.579  -9.212   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.318  -6.734   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.072  -8.892   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.744  -9.217   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.205 -10.619   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.737 -10.780   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      17.363 -12.187   0.000  0.00  0.00           O+0
HETATM   19  P   UNK     0      18.894 -12.348   0.000  0.00  0.00           P+0
HETATM   20  O   UNK     0      20.426 -12.509   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      19.055 -10.816   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      18.733 -13.879   0.000  0.00  0.00           O+0
HETATM   23  P   UNK     0      21.052 -13.916   0.000  0.00  0.00           P+0
HETATM   24  O   UNK     0      19.646 -14.542   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      22.459 -13.289   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      21.679 -15.323   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.638  -5.228   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.103  -4.752   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.494  -4.197   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.814  -2.691   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.029  -4.673   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.670  -1.660   0.000  0.00  0.00           C+0
CONECT    1    2    3    8                                                  
CONECT    2    1    4    9                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5    7                                                  
CONECT    7    6                                                            
CONECT    8    1   10                                                       
CONECT    9    2                                                            
CONECT   10    8   13   14                                                  
CONECT   11   12   13                                                       
CONECT   12   11   14   16                                                  
CONECT   13   11   10   27                                                  
CONECT   14   10   12   15                                                  
CONECT   15   14                                                            
CONECT   16   12   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19   23                                                       
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23   20   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   13   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29   32                                                       
CONECT   31   29                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

COMPND    HMDB0012310
HETATM    1  C1  UNL     1      -3.681  -4.916   0.153  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.685  -3.817  -0.262  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.490  -2.570  -0.405  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.595  -2.728  -1.446  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.657  -1.360  -0.871  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.127  -1.723  -2.104  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.489  -1.150   0.062  1.00  0.00           C  
HETATM    8  S1  UNL     1      -0.125  -2.193   0.262  1.00  0.00           S  
HETATM    9  C7  UNL     1       0.653  -1.343   1.499  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.931  -1.716   2.164  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.104  -0.905   1.741  1.00  0.00           C  
HETATM   12  O2  UNL     1       3.380  -0.991   0.373  1.00  0.00           O  
HETATM   13  P1  UNL     1       4.732  -0.036   0.009  1.00  0.00           P  
HETATM   14  O3  UNL     1       4.835   1.038   1.097  1.00  0.00           O  
HETATM   15  O4  UNL     1       6.144  -0.991   0.021  1.00  0.00           O  
HETATM   16  O5  UNL     1       4.545   0.751  -1.473  1.00  0.00           O  
HETATM   17  P2  UNL     1       5.972   1.536  -1.870  1.00  0.00           P  
HETATM   18  O6  UNL     1       5.726   2.972  -2.294  1.00  0.00           O  
HETATM   19  O7  UNL     1       6.993   1.522  -0.532  1.00  0.00           O  
HETATM   20  O8  UNL     1       6.710   0.674  -3.122  1.00  0.00           O  
HETATM   21  C10 UNL     1      -0.180  -0.281   1.703  1.00  0.00           C  
HETATM   22  C11 UNL     1       0.197   0.719   2.790  1.00  0.00           C  
HETATM   23  N1  UNL     1      -1.262  -0.195   0.965  1.00  0.00           N1+
HETATM   24  C12 UNL     1      -2.232   0.913   1.153  1.00  0.00           C  
HETATM   25  C13 UNL     1      -1.812   2.191   0.583  1.00  0.00           C  
HETATM   26  C14 UNL     1      -1.470   3.214   1.486  1.00  0.00           C  
HETATM   27  N2  UNL     1      -1.096   4.432   1.061  1.00  0.00           N  
HETATM   28  C15 UNL     1      -1.034   4.722  -0.243  1.00  0.00           C  
HETATM   29  C16 UNL     1      -0.612   6.093  -0.678  1.00  0.00           C  
HETATM   30  N3  UNL     1      -1.354   3.769  -1.130  1.00  0.00           N  
HETATM   31  C17 UNL     1      -1.741   2.512  -0.728  1.00  0.00           C  
HETATM   32  N4  UNL     1      -2.032   1.634  -1.795  1.00  0.00           N  
HETATM   33  H1  UNL     1      -4.355  -4.536   0.934  1.00  0.00           H  
HETATM   34  H2  UNL     1      -4.266  -5.171  -0.745  1.00  0.00           H  
HETATM   35  H3  UNL     1      -3.129  -5.802   0.528  1.00  0.00           H  
HETATM   36  H4  UNL     1      -2.114  -4.108  -1.147  1.00  0.00           H  
HETATM   37  H5  UNL     1      -2.030  -3.676   0.642  1.00  0.00           H  
HETATM   38  H6  UNL     1      -3.918  -2.290   0.575  1.00  0.00           H  
HETATM   39  H7  UNL     1      -5.362  -3.430  -1.067  1.00  0.00           H  
HETATM   40  H8  UNL     1      -4.116  -3.051  -2.385  1.00  0.00           H  
HETATM   41  H9  UNL     1      -5.031  -1.728  -1.600  1.00  0.00           H  
HETATM   42  H10 UNL     1      -3.307  -0.486  -0.937  1.00  0.00           H  
HETATM   43  H11 UNL     1      -1.195  -2.067  -2.015  1.00  0.00           H  
HETATM   44  H12 UNL     1       2.153  -2.779   1.996  1.00  0.00           H  
HETATM   45  H13 UNL     1       1.850  -1.603   3.280  1.00  0.00           H  
HETATM   46  H14 UNL     1       3.993  -1.316   2.275  1.00  0.00           H  
HETATM   47  H15 UNL     1       3.040   0.163   2.036  1.00  0.00           H  
HETATM   48  H16 UNL     1       5.914  -1.863  -0.384  1.00  0.00           H  
HETATM   49  H17 UNL     1       7.224   2.425  -0.201  1.00  0.00           H  
HETATM   50  H18 UNL     1       7.391   0.081  -2.724  1.00  0.00           H  
HETATM   51  H19 UNL     1       0.892   0.264   3.522  1.00  0.00           H  
HETATM   52  H20 UNL     1       0.708   1.550   2.326  1.00  0.00           H  
HETATM   53  H21 UNL     1      -0.685   1.030   3.344  1.00  0.00           H  
HETATM   54  H22 UNL     1      -2.406   0.988   2.252  1.00  0.00           H  
HETATM   55  H23 UNL     1      -3.227   0.615   0.753  1.00  0.00           H  
HETATM   56  H24 UNL     1      -1.496   3.080   2.558  1.00  0.00           H  
HETATM   57  H25 UNL     1      -1.277   6.858  -0.216  1.00  0.00           H  
HETATM   58  H26 UNL     1      -0.632   6.173  -1.776  1.00  0.00           H  
HETATM   59  H27 UNL     1       0.416   6.301  -0.271  1.00  0.00           H  
HETATM   60  H28 UNL     1      -1.322   0.961  -2.145  1.00  0.00           H  
HETATM   61  H29 UNL     1      -2.963   1.639  -2.256  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3   36   37
CONECT    3    4    5   38
CONECT    4   39   40   41
CONECT    5    6    7   42
CONECT    6   43
CONECT    7    8   23   23
CONECT    8    9
CONECT    9   10   21   21
CONECT   10   11   44   45
CONECT   11   12   46   47
CONECT   12   13
CONECT   13   14   14   15   16
CONECT   15   48
CONECT   16   17
CONECT   17   18   18   19   20
CONECT   19   49
CONECT   20   50
CONECT   21   22   23
CONECT   22   51   52   53
CONECT   23   24
CONECT   24   25   54   55
CONECT   25   26   26   31
CONECT   26   27   56
CONECT   27   28   28
CONECT   28   29   30
CONECT   29   57   58   59
CONECT   30   31   31
CONECT   31   32
CONECT   32   60   61
END

HMDB0012310
     RDKit          3D
2-Methyl-1-hydroxybutyl-ThPP
 61 62  0  0  0  0  0  0  0  0999 V2000
   -3.6807   -4.9158    0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6852   -3.8166   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896   -2.5701   -0.4054 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  CHG  1  23   1
M  END

Synonyms

Value	Source
2-Methyl-1-hydroxybutyl-TPP	Kegg

Molecular Formula

C₁₇H₂₉N₄O₈P₂S

Average Mass

511.447

Monoisotopic Mass

511.118132638

IUPAC Name

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

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(O)C1=[N+](CC2=CN=C(C)N=C2N)C(C)=C(CCOP(O)(=O)OP(O)(O)=O)S1

InChI Identifier

InChI=1S/C17H28N4O8P2S/c1-5-10(2)15(22)17-21(9-13-8-19-12(4)20-16(13)18)11(3)14(32-17)6-7-28-31(26,27)29-30(23,24)25/h8,10,15,22H,5-7,9H2,1-4H3,(H4-,18,19,20,23,24,25,26,27)/p+1/t10-,15?/m0/s1

InChI Key

CUBSXOWPMAOFDG-MYHCZTBNSA-O

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:80223 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.074 g/L	ALOGPS
logP	-0.18	ALOGPS
logP	-5.6	ChemAxon
logS	-3.9	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	11	ChemAxon
Refractivity	130.18 m³·mol⁻¹	ChemAxon
Polarizability	48.11 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191969	2-oxoisovalerate dehydrogenase subunit beta, mitochondrial	Enzyme	P21953	Homo sapiens
MMDBp0191970	2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial	Unknown	P12694	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	35	Human feces; Human sputum; Human ; Human pleural fluid plaque	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	90	Human feces; Human ; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	12	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	8	Human feces; Human ; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Actinobacteria	1	Human feces; Human	Metabolic reconstruction
Bacteria	Firmicutes	2	Human feces; Human ; Human subgingival plaque	Metabolic reconstruction
Bacteria	Proteobacteria	1	Human feces; Human sputum; Human ; Human pleural fluid plaque	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0012310

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028932

KNApSAcK ID

Not Available

Chemspider ID

35031876

KEGG Compound ID

C15978

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23724627

PDB ID

Not Available

ChEBI ID

80223

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for 2-Methyl-1-hydroxybutyl-ThPP (MMDBc0049903)

MOL for #<Metabolite:0x00007f9258088fa8>

3D MOL for #<Metabolite:0x00007f9258088fa8>

3D SDF for #<Metabolite:0x00007f9258088fa8>

3D-SDF for #<Metabolite:0x00007f9258088fa8>

PDB for #<Metabolite:0x00007f9258088fa8>

3D PDB for #<Metabolite:0x00007f9258088fa8>

SMILES for #<Metabolite:0x00007f9258088fa8>

INCHI for #<Metabolite:0x00007f9258088fa8>

Structure for #<Metabolite:0x00007f9258088fa8>

3D Structure for #<Metabolite:0x00007f9258088fa8>