MiMeDB: Showing metabocard for 3-Carboxy-1-hydroxypropylthiamine diphosphate (MMDBc0047954)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:18:41 UTC

Update Date

2022-09-01 02:13:05 UTC

Metabolite ID

MMDBc0047954

Metabolite Identification

Common Name

3-Carboxy-1-hydroxypropylthiamine diphosphate

Description

3-Carboxy-1-hydroxypropyl-ThPP is an intermediate in Citrate cycle (TCA cycle). 3-Carboxy-1-hydroxypropyl-ThPP is the second to last step in the synthesis of Succinyl-CoA and is converted from 2-Oxoglutarate via the enzyme 2-oxoglutarate dehydrogenase E1 component (EC.1.2.4.2). It is then converted to S-Succinyldihydrolipoamide-E via the enzyme 2-oxoglutarate dehydrogenase E1 component (EC.1.2.4.2).

Structure

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

 
  Mrv0541 02231220502D          
 
 33 34  0  0  0  0            999 V2000
   22.8196   -6.5262    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   23.1983   -5.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4013   -7.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1035   -6.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0107   -5.9272    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.8264   -5.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1347   -6.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3083   -7.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3909   -6.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0072   -5.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2809   -4.3678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8679   -7.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3909   -7.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6680   -6.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5599   -6.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6680   -7.7828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1035   -7.7724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9588   -6.5298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2931   -7.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9588   -7.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9851   -6.6020    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.2462   -7.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7183   -6.9807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1950   -7.4695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4103   -6.5331    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.1401   -6.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6203   -7.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9851   -5.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4103   -5.7081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6354   -4.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8049   -4.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3511   -4.9073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4365   -3.4834    0.0000 O   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
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  CHG  1   1   1
M  END

HMDB0006744
     RDKit          3D
3-Carboxy-1-hydroxypropylthiamine diphosphate
 58 59  0  0  0  0  0  0  0  0999 V2000
   -5.3754    4.8155   -2.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6009    3.5319   -2.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    3.1781   -2.8146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185    2.0337   -2.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2306    1.1418   -1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4396   -0.0639   -1.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3023   -0.0125   -0.4826 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.4421   -0.4002    0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5643   -1.0411    1.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8695   -0.1488    2.5705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9441   -2.2394    2.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3139   -3.2414    1.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1863   -3.8932    0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4021   -3.6514    0.3549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6127   -4.8160   -0.4256 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126   -0.1335    1.4974 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8807    0.4734    0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3273    0.9197   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1362    0.2455    1.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4519    0.6546    0.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4634   -0.0089    2.0775 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.0590    0.5826    3.4276 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4333   -1.6756    2.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0504    0.5044    1.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8158   -0.4398    0.6134 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.9184   -0.7168   -0.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2083    0.3382    0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3016   -1.9366    1.2439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1031    0.4408   -0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2385    0.8797   -2.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2646    1.5303   -0.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8068    0.7808    0.2914 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9211    2.7091   -1.0217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0386    4.6130   -3.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6653    5.6073   -2.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9327    5.0731   -1.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    1.8165   -3.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0836   -0.4124   -2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175   -0.9178   -1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602   -1.4362    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0468    0.3114    2.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1968   -1.8755    3.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365   -2.7527    2.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9182   -4.0567    2.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753   -2.8675    0.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0462   -5.7027   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449    0.5837   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3239    1.9955    0.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0874   -0.8502    0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6781    0.5166    2.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7854   -2.0068    1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0518    0.6589   -0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5433   -2.5473    0.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119    0.2682   -3.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    1.9685   -2.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3010    0.6942   -2.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1981   -0.1904    0.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8446    1.1682    1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  8 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 17 29  2  0
 29 30  1  0
  5 31  1  0
 31 32  1  0
 31 33  2  0
 33  2  1  0
 29  7  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 15 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 23 51  1  0
 27 52  1  0
 28 53  1  0
 30 54  1  0
 30 55  1  0
 30 56  1  0
 32 57  1  0
 32 58  1  0
M  CHG  1   7   1
M  END

 
  Mrv0541 02231220502D          
 
 33 34  0  0  0  0            999 V2000
   22.8196   -6.5262    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   23.1983   -5.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4013   -7.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1035   -6.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0107   -5.9272    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.8264   -5.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1347   -6.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3083   -7.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3909   -6.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0072   -5.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2809   -4.3678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8679   -7.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3909   -7.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6680   -6.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5599   -6.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6680   -7.7828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1035   -7.7724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9588   -6.5298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2931   -7.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9588   -7.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9851   -6.6020    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.2462   -7.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7183   -6.9807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1950   -7.4695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4103   -6.5331    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.1401   -6.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6203   -7.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9851   -5.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4103   -5.7081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6354   -4.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8049   -4.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3511   -4.9073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4365   -3.4834    0.0000 O   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
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  CHG  1   1   1
M  END
> <DATABASE_ID>
MMDBc0047954

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC(C(O)CCC(O)=O)=[N+]1CC1=C(N)N=C(C)N=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H24N4O10P2S/c1-9-13(5-6-29-32(27,28)30-31(24,25)26)33-16(12(21)3-4-14(22)23)20(9)8-11-7-18-10(2)19-15(11)17/h7,12,21H,3-6,8H2,1-2H3,(H5-,17,18,19,22,23,24,25,26,27,28)/p+1

> <INCHI_KEY>
ZWUKRGPVMMTMAF-UHFFFAOYSA-O

> <FORMULA>
C16H25N4O10P2S

> <MOLECULAR_WEIGHT>
527.403

> <EXACT_MASS>
527.076661754

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
47.108163008895595

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.64

> <JCHEM_LOGP>
-7.2914789016294765

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.099590167678406

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.773930796829486

> <JCHEM_PKA_STRONGEST_BASIC>
5.538537381625124

> <JCHEM_POLAR_SURFACE_AREA>
226.49999999999997

> <JCHEM_REFRACTIVITY>
127.36989999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-carboxy-1-hydroxypropyl-thpp

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006744
     RDKit          3D
3-Carboxy-1-hydroxypropylthiamine diphosphate
 58 59  0  0  0  0  0  0  0  0999 V2000
   -5.3754    4.8155   -2.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6009    3.5319   -2.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    3.1781   -2.8146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185    2.0337   -2.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2306    1.1418   -1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4396   -0.0639   -1.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3023   -0.0125   -0.4826 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.4421   -0.4002    0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5643   -1.0411    1.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8695   -0.1488    2.5705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9441   -2.2394    2.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3139   -3.2414    1.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1863   -3.8932    0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4021   -3.6514    0.3549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6127   -4.8160   -0.4256 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126   -0.1335    1.4974 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8807    0.4734    0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3273    0.9197   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1362    0.2455    1.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4519    0.6546    0.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4634   -0.0089    2.0775 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.0590    0.5826    3.4276 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4333   -1.6756    2.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0504    0.5044    1.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8158   -0.4398    0.6134 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.9184   -0.7168   -0.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2083    0.3382    0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3016   -1.9366    1.2439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1031    0.4408   -0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2385    0.8797   -2.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2646    1.5303   -0.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8068    0.7808    0.2914 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9211    2.7091   -1.0217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0386    4.6130   -3.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6653    5.6073   -2.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9327    5.0731   -1.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    1.8165   -3.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0836   -0.4124   -2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175   -0.9178   -1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602   -1.4362    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0468    0.3114    2.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1968   -1.8755    3.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365   -2.7527    2.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9182   -4.0567    2.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753   -2.8675    0.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0462   -5.7027   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449    0.5837   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3239    1.9955    0.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0874   -0.8502    0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6781    0.5166    2.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7854   -2.0068    1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0518    0.6589   -0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5433   -2.5473    0.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119    0.2682   -3.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    1.9685   -2.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3010    0.6942   -2.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1981   -0.1904    0.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8446    1.1682    1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  8 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 17 29  2  0
 29 30  1  0
  5 31  1  0
 31 32  1  0
 31 33  2  0
 33  2  1  0
 29  7  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 15 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 23 51  1  0
 27 52  1  0
 28 53  1  0
 30 54  1  0
 30 55  1  0
 30 56  1  0
 32 57  1  0
 32 58  1  0
M  CHG  1   7   1
M  END

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      42.597 -12.182   0.000  0.00  0.00           N+1
HETATM    2  C   UNK     0      43.303 -10.814   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      43.682 -13.275   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      41.260 -11.418   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0      44.820 -11.064   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0      42.609  -9.438   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      45.051 -12.581   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      43.509 -14.798   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      39.930 -12.189   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      41.080  -9.349   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      43.458  -8.153   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      46.420 -13.288   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      39.930 -13.737   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.580 -11.424   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      47.712 -12.452   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      38.580 -14.528   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      41.260 -14.508   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      37.256 -12.189   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      49.080 -13.159   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      37.256 -13.737   0.000  0.00  0.00           C+0
HETATM   21  P   UNK     0      50.372 -12.324   0.000  0.00  0.00           P+0
HETATM   22  C   UNK     0      35.926 -14.508   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      51.741 -13.031   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      50.764 -13.943   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      53.033 -12.195   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0      54.395 -12.896   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      53.425 -13.814   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      50.372 -10.784   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      53.033 -10.655   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      40.386  -7.965   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      38.836  -7.874   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      37.989  -9.160   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      38.148  -6.502   0.000  0.00  0.00           O+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                                                       
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   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

COMPND    HMDB0006744
HETATM    1  C1  UNL     1      -5.375   4.815  -2.209  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.601   3.532  -2.016  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.594   3.178  -2.815  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.919   2.034  -2.632  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.231   1.142  -1.588  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.440  -0.064  -1.443  1.00  0.00           C  
HETATM    7  N2  UNL     1      -1.302  -0.012  -0.483  1.00  0.00           N1+
HETATM    8  C6  UNL     1      -1.442  -0.400   0.773  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.564  -1.041   1.543  1.00  0.00           C  
HETATM   10  O1  UNL     1      -2.869  -0.149   2.571  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.944  -2.239   2.298  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.314  -3.241   1.408  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.186  -3.893   0.435  1.00  0.00           C  
HETATM   14  O2  UNL     1      -3.402  -3.651   0.355  1.00  0.00           O  
HETATM   15  O3  UNL     1      -1.613  -4.816  -0.426  1.00  0.00           O  
HETATM   16  S1  UNL     1       0.113  -0.133   1.497  1.00  0.00           S  
HETATM   17  C11 UNL     1       0.881   0.473   0.103  1.00  0.00           C  
HETATM   18  C12 UNL     1       2.327   0.920  -0.038  1.00  0.00           C  
HETATM   19  C13 UNL     1       3.136   0.246   1.061  1.00  0.00           C  
HETATM   20  O4  UNL     1       4.452   0.655   0.913  1.00  0.00           O  
HETATM   21  P1  UNL     1       5.463  -0.009   2.077  1.00  0.00           P  
HETATM   22  O5  UNL     1       5.059   0.583   3.428  1.00  0.00           O  
HETATM   23  O6  UNL     1       5.433  -1.676   2.122  1.00  0.00           O  
HETATM   24  O7  UNL     1       7.050   0.504   1.788  1.00  0.00           O  
HETATM   25  P2  UNL     1       7.816  -0.440   0.613  1.00  0.00           P  
HETATM   26  O8  UNL     1       6.918  -0.717  -0.571  1.00  0.00           O  
HETATM   27  O9  UNL     1       9.208   0.338   0.070  1.00  0.00           O  
HETATM   28  O10 UNL     1       8.302  -1.937   1.244  1.00  0.00           O  
HETATM   29  C14 UNL     1      -0.103   0.441  -0.850  1.00  0.00           C  
HETATM   30  C15 UNL     1       0.238   0.880  -2.262  1.00  0.00           C  
HETATM   31  C16 UNL     1      -4.265   1.530  -0.791  1.00  0.00           C  
HETATM   32  N3  UNL     1      -4.807   0.781   0.291  1.00  0.00           N  
HETATM   33  N4  UNL     1      -4.921   2.709  -1.022  1.00  0.00           N  
HETATM   34  H1  UNL     1      -6.039   4.613  -3.087  1.00  0.00           H  
HETATM   35  H2  UNL     1      -4.665   5.607  -2.537  1.00  0.00           H  
HETATM   36  H3  UNL     1      -5.933   5.073  -1.296  1.00  0.00           H  
HETATM   37  H4  UNL     1      -2.119   1.816  -3.351  1.00  0.00           H  
HETATM   38  H5  UNL     1      -2.084  -0.412  -2.451  1.00  0.00           H  
HETATM   39  H6  UNL     1      -3.118  -0.918  -1.134  1.00  0.00           H  
HETATM   40  H7  UNL     1      -3.360  -1.436   0.965  1.00  0.00           H  
HETATM   41  H8  UNL     1      -2.047   0.311   2.831  1.00  0.00           H  
HETATM   42  H9  UNL     1      -1.197  -1.875   3.028  1.00  0.00           H  
HETATM   43  H10 UNL     1      -2.736  -2.753   2.888  1.00  0.00           H  
HETATM   44  H11 UNL     1      -0.918  -4.057   2.086  1.00  0.00           H  
HETATM   45  H12 UNL     1      -0.375  -2.867   0.913  1.00  0.00           H  
HETATM   46  H13 UNL     1      -2.046  -5.703  -0.595  1.00  0.00           H  
HETATM   47  H14 UNL     1       2.645   0.584  -1.037  1.00  0.00           H  
HETATM   48  H15 UNL     1       2.324   1.996   0.012  1.00  0.00           H  
HETATM   49  H16 UNL     1       3.087  -0.850   0.867  1.00  0.00           H  
HETATM   50  H17 UNL     1       2.678   0.517   2.021  1.00  0.00           H  
HETATM   51  H18 UNL     1       5.785  -2.007   1.242  1.00  0.00           H  
HETATM   52  H19 UNL     1       9.052   0.659  -0.836  1.00  0.00           H  
HETATM   53  H20 UNL     1       8.543  -2.547   0.511  1.00  0.00           H  
HETATM   54  H21 UNL     1      -0.312   0.268  -3.013  1.00  0.00           H  
HETATM   55  H22 UNL     1       0.070   1.968  -2.375  1.00  0.00           H  
HETATM   56  H23 UNL     1       1.301   0.694  -2.503  1.00  0.00           H  
HETATM   57  H24 UNL     1      -5.198  -0.190   0.152  1.00  0.00           H  
HETATM   58  H25 UNL     1      -4.845   1.168   1.255  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    3   33
CONECT    3    4
CONECT    4    5    5   37
CONECT    5    6   31
CONECT    6    7   38   39
CONECT    7    8    8   29
CONECT    8    9   16
CONECT    9   10   11   40
CONECT   10   41
CONECT   11   12   42   43
CONECT   12   13   44   45
CONECT   13   14   14   15
CONECT   15   46
CONECT   16   17
CONECT   17   18   29   29
CONECT   18   19   47   48
CONECT   19   20   49   50
CONECT   20   21
CONECT   21   22   22   23   24
CONECT   23   51
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   27   52
CONECT   28   53
CONECT   29   30
CONECT   30   54   55   56
CONECT   31   32   33   33
CONECT   32   57   58
END

HMDB0006744
     RDKit          3D
3-Carboxy-1-hydroxypropylthiamine diphosphate
 58 59  0  0  0  0  0  0  0  0999 V2000
   -5.3754    4.8155   -2.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6009    3.5319   -2.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    3.1781   -2.8146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185    2.0337   -2.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2306    1.1418   -1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4396   -0.0639   -1.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3023   -0.0125   -0.4826 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.4421   -0.4002    0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5643   -1.0411    1.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8695   -0.1488    2.5705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9441   -2.2394    2.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3139   -3.2414    1.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1863   -3.8932    0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4021   -3.6514    0.3549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6127   -4.8160   -0.4256 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126   -0.1335    1.4974 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8807    0.4734    0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3273    0.9197   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1362    0.2455    1.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4519    0.6546    0.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4634   -0.0089    2.0775 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.0590    0.5826    3.4276 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4333   -1.6756    2.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0504    0.5044    1.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8158   -0.4398    0.6134 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.9184   -0.7168   -0.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2083    0.3382    0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3016   -1.9366    1.2439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1031    0.4408   -0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2385    0.8797   -2.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2646    1.5303   -0.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8068    0.7808    0.2914 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9211    2.7091   -1.0217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0386    4.6130   -3.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6653    5.6073   -2.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9327    5.0731   -1.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    1.8165   -3.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0836   -0.4124   -2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175   -0.9178   -1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602   -1.4362    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0468    0.3114    2.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1968   -1.8755    3.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365   -2.7527    2.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9182   -4.0567    2.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753   -2.8675    0.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0462   -5.7027   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449    0.5837   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3239    1.9955    0.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0874   -0.8502    0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6781    0.5166    2.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7854   -2.0068    1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0518    0.6589   -0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5433   -2.5473    0.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119    0.2682   -3.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    1.9685   -2.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3010    0.6942   -2.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1981   -0.1904    0.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8446    1.1682    1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  8 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 17 29  2  0
 29 30  1  0
  5 31  1  0
 31 32  1  0
 31 33  2  0
 33  2  1  0
 29  7  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 15 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 23 51  1  0
 27 52  1  0
 28 53  1  0
 30 54  1  0
 30 55  1  0
 30 56  1  0
 32 57  1  0
 32 58  1  0
M  CHG  1   7   1
M  END

Synonyms

Value	Source
2-(3-Carboxy-1-hydroxypropyl)thiamine diphosphate	ChEBI
3-Carboxy-1-hydroxypropyl-THPP	ChEBI
Succinate semialdehyde-thiamin diphosphate	Kegg
2-(3-Carboxy-1-hydroxypropyl)thiamine diphosphoric acid	Generator
Succinic acid semialdehyde-thiamin diphosphoric acid	Generator
3-Carboxy-1-hydroxypropylthiamine diphosphoric acid	Generator
3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-2-(3-carboxy-1-hydroxypropyl)-5-(2-diphosphoethyl)-4-methyl-1,3-thiazol-3-ium	HMDB

Molecular Formula

C₁₆H₂₅N₄O₁₀P₂S

Average Mass

527.403

Monoisotopic Mass

527.076661754

IUPAC Name

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

Traditional Name

3-carboxy-1-hydroxypropyl-thpp

CAS Registry Number

Not Available

SMILES

CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC(C(O)CCC(O)=O)=[N+]1CC1=C(N)N=C(C)N=C1

InChI Identifier

InChI=1S/C16H24N4O10P2S/c1-9-13(5-6-29-32(27,28)30-31(24,25)26)33-16(12(21)3-4-14(22)23)20(9)8-11-7-18-10(2)19-15(11)17/h7,12,21H,3-6,8H2,1-2H3,(H5-,17,18,19,22,23,24,25,26,27,28)/p+1

InChI Key

ZWUKRGPVMMTMAF-UHFFFAOYSA-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
Imidolactam
Phosphoric acid ester
Alkyl phosphate
Azole
Heteroaromatic compound
Thiazole
Amino acid or derivatives
Amino acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organonitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Amine
Alcohol
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organooxygen compound
Primary amine
Aromatic alcohol
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3-thiazolium cation (CHEBI:1463 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.054 g/L	ALOGPS
logP	-0.64	ALOGPS
logP	-7.3	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	1.77	ChemAxon
pKa (Strongest Basic)	5.54	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	226.5 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	127.37 m³·mol⁻¹	ChemAxon
Polarizability	47.11 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ki2-8853930000-2d20db61c35c735c6726	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0002-8080197000-6f52c57ca3a187968f4b	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-055e-0246950000-bac6074dcea868b654a7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-4319200000-b9cec10cb173f2d20023	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dj-1962000000-76c3988b185ec2f13f69	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05di-0300960000-6d763b4c58b5627dbbe3	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004j-0205910000-63d4b7f4c17e449a6f57	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-2937100000-ab1d8c9956ba46638067	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

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
MMDBp0192105	2-oxoglutarate dehydrogenase, mitochondrial	Enzyme	Q02218	Homo sapiens
MMDBp0195852	2-oxoglutarate dehydrogenase-like, mitochondrial	Enzyme	Q9ULD0	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0002472	Oxoglutaric acid	Carbon dioxide	Oxoglutarate (alpha-ketoglutarate) dehydrogenase (lipoamide)	2-Oxoglutarate Dehydrogenase E1 Component	VMH	10676873 3207422
MMDBr0002627	3-Carboxy-1-hydroxypropylthiamine diphosphate	(S)-Succinyldihydrolipoamide	Oxoglutarate (alpha-ketoglutarate) dehydrogenase (lipoamide)	2-Oxoglutarate Dehydrogenase E1 Component	VMH	10676873
MMDBr0007677	3-Carboxy-1-hydroxypropylthiamine diphosphate	(S)-Succinyldihydrolipoamide	Not Available	3-Carboxy-1-hydroxypropyl-ThPP:lipoamide	VMH	30371894
MMDBr0008013	Oxoglutaric acid	Carbon dioxide	Not Available	2-oxoglutarate dehydrogenase	VMH	30371894

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	Proteobacteria	147	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Actinobacteria	49	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Firmicutes	65	Human feces; Human ; Human subgingival plaque	Metabolic reconstruction
Bacteria	Bacteroidetes	8	Human feces; Human ; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	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

HMDB0006744

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024054

KNApSAcK ID

Not Available

Chemspider ID

389531

KEGG Compound ID

C05381

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440649

PDB ID

Not Available

ChEBI ID

1463

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 3-Carboxy-1-hydroxypropylthiamine diphosphate (MMDBc0047954)

MOL for #<Metabolite:0x000055d24ae6ce50>

3D MOL for #<Metabolite:0x000055d24ae6ce50>

3D SDF for #<Metabolite:0x000055d24ae6ce50>

3D-SDF for #<Metabolite:0x000055d24ae6ce50>

PDB for #<Metabolite:0x000055d24ae6ce50>

3D PDB for #<Metabolite:0x000055d24ae6ce50>

SMILES for #<Metabolite:0x000055d24ae6ce50>

INCHI for #<Metabolite:0x000055d24ae6ce50>

Structure for #<Metabolite:0x000055d24ae6ce50>

3D Structure for #<Metabolite:0x000055d24ae6ce50>