MiMeDB: Showing metabocard for dTDP-beta-L-rhamnose (MMDBc0054471)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:14:17 UTC

Update Date

2024-04-20 06:11:48 UTC

Metabolite ID

MMDBc0054471

Metabolite Identification

Common Name

dTDP-beta-L-rhamnose

Description

Deoxythymidine diphosphate-L-rhamnose (dTDP-L-rhamnose) is the precursor of L-rhamnose, a saccharide required for the virulence of some pathogenic bacteria. In gram-negative bacteria such as Salmonella enterica, Vibrio cholerae, or Escherichia coli 075:K5, L-rhamnose is an important residue in the O-antigen of lipopolysaccharides, which are essential for resistance to serum killing and colonization. In gram-positive bacteria such as streptococci, the capsule is a recognized virulence factor. For example, L-rhamnose is known to be present in the capsule of Streptococcus suis, a causative agent of meningitis in humans. In Streptococcus mutans, L-rhamnose containing polysaccharides have been implicated in tooth surface colonization and adherence to kidney, muscle, and heart tissues. In mycobacteria, L-rhamnose is fundamental to the structural integrity of the cell wall since it connects the inner peptidoglycan layer to the arabinogalactan polysaccharides. dTDP-L-rhamnose is synthesized from glucose-1-phosphate and deoxythymidine triphosphate (dTTP) via a pathway involving four distinct enzymes. Whereas common sugars such as glucose, fructose, and mannose are all D-configured, bacteria commonly utilize the L-configured carbohydrates in pharmacologically active compounds and their cell-wall structures. The bacterial cell wall is unique to bacteria; neither the cell wall nor the enzymes and chemical intermediates in its formation have analogues in humans. The enzymes involved in dTDP-L-rhamnose synthesis are potential targets for the design of new therapeutic agents (PMID: 10802738 , 12773151 ).

Structure

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


  Mrv1652309042000322D          

 35 37  0  0  0  0            999 V2000
 9995.5529 9998.6406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.121910001.1147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.552910001.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0311 9999.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5233 9998.0181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7455 9999.4656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.4604 9999.8770    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10001.3741 9999.3550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.047910000.5909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.872910000.5909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.2857 9999.8812    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10003.0014 9999.4676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.873210000.5950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.698210000.5950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.4287 9998.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.8580 9999.4676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.428710001.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.858010001.1168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.429310001.1183    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.714810000.7058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.7148 9999.8807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10004.4293 9999.4683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10005.1438 9999.8807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10005.143810000.7058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.6452 9999.9598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9778 9999.4748    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.2327 9998.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0577 9998.6902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.3126 9999.4748    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.551510001.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.837010000.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8370 9999.8772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5515 9999.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2660 9999.8772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.266010000.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
 19 24  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 12  1  1  0  0  0
 22 15  1  1  0  0  0
 23 16  1  1  0  0  0
 19 17  1  1  0  0  0
 24 18  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 26  1  0  0  0  0
 25 29  1  0  0  0  0
 29  4  1  6  0  0  0
 28  5  1  1  0  0  0
 30 31  1  0  0  0  0
 30 35  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  1 33  2  0  0  0  0
 26 34  1  6  0  0  0
 31  2  2  0  0  0  0
 30  3  1  0  0  0  0
M  END

HMDB0006354
     RDKit          3D
Deoxythymidine diphosphate-L-rhamnose
 61 63  0  0  0  0  0  0  0  0999 V2000
   -6.4009    3.1354   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6691    1.7750    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6956    0.8031    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9497   -0.4500    0.4355 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8900   -1.4298    0.2688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5280   -1.5816   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0729   -2.0730   -1.0411 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1412   -3.4692   -0.8600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6666   -1.4050    0.2002 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6391   -0.3115   -0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5149   -0.9309   -0.6313 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7549   -0.8345    0.4863 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.6730   -2.3090    1.1334 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3367    0.1519    1.7598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2769   -0.6996   -0.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1911   -1.9366    0.6576 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.6659   -3.2523    0.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9204   -1.8426    2.3439 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247   -1.8181    0.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9888   -0.5865   -0.3714 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7102    0.3540    0.6469 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0769    1.6266    0.3381 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0354    2.1266    1.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6229    1.8352   -1.0296 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6058    1.6396   -1.9725 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7321    0.8779   -1.3681 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9511    1.3103   -0.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3558   -0.5065   -0.8801 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3027   -0.8272    0.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7360   -0.9627    0.8962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1440   -0.7471    0.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3679   -1.9005    1.3038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1452    0.1719    1.0732 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9147    1.4549    0.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7729    2.3361    0.7511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6354    3.9526    0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0332    3.2498   -1.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3260    3.2295   -0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7314    1.0781   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2250   -2.4049    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5244   -0.5937   -1.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1324   -2.3230   -1.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4464   -1.8268   -1.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6853   -3.6563    0.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1482   -2.2143    0.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0871    0.3093   -0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4686    0.3673    0.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1262    1.0606    1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0474   -2.7570    2.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2031   -0.5609   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1608    2.2894    0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0646    3.2077    1.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6307    1.7702    2.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0325    1.6600    1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9129    2.8998   -1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9950    1.3953   -2.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8434    0.8845   -2.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0038    2.3057   -0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5406   -1.2156   -1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1759   -1.7225    0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0705   -0.1091    1.4634 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
  9 30  1  0
  4 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 34 35  2  0
 34  2  1  0
 30  5  1  0
 28 20  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  5 40  1  1
  6 41  1  0
  6 42  1  0
  7 43  1  6
  8 44  1  0
  9 45  1  1
 10 46  1  0
 10 47  1  0
 14 48  1  0
 18 49  1  0
 20 50  1  6
 22 51  1  6
 23 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  1
 25 56  1  0
 26 57  1  6
 27 58  1  0
 28 59  1  6
 29 60  1  0
 33 61  1  0
M  END


  Mrv1652309042000322D          

 35 37  0  0  0  0            999 V2000
 9995.5529 9998.6406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.121910001.1147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.552910001.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0311 9999.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5233 9998.0181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7455 9999.4656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.4604 9999.8770    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10001.3741 9999.3550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.047910000.5909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.872910000.5909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.2857 9999.8812    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10003.0014 9999.4676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.873210000.5950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.698210000.5950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.4287 9998.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.8580 9999.4676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.428710001.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.858010001.1168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.429310001.1183    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.714810000.7058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.7148 9999.8807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10004.4293 9999.4683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10005.1438 9999.8807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10005.143810000.7058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.6452 9999.9598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9778 9999.4748    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.2327 9998.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0577 9998.6902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.3126 9999.4748    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.551510001.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.837010000.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8370 9999.8772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5515 9999.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2660 9999.8772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.266010000.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
 19 24  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 12  1  1  0  0  0
 22 15  1  1  0  0  0
 23 16  1  1  0  0  0
 19 17  1  1  0  0  0
 24 18  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 26  1  0  0  0  0
 25 29  1  0  0  0  0
 29  4  1  6  0  0  0
 28  5  1  1  0  0  0
 30 31  1  0  0  0  0
 30 35  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  1 33  2  0  0  0  0
 26 34  1  6  0  0  0
 31  2  2  0  0  0  0
 30  3  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054471

> <DATABASE_NAME>
MIME

> <SMILES>
C[C@@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H](C[C@@H]2O)N2C=C(C)C(=O)NC2=O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H26N2O15P2/c1-6-4-18(16(24)17-14(6)23)10-3-8(19)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(20)7(2)30-15/h4,7-13,15,19-22H,3,5H2,1-2H3,(H,25,26)(H,27,28)(H,17,23,24)/t7-,8-,9+,10+,11-,12+,13+,15+/m0/s1

> <INCHI_KEY>
ZOSQFDVXNQFKBY-CGAXJHMRSA-N

> <FORMULA>
C16H26N2O15P2

> <MOLECULAR_WEIGHT>
548.3296

> <EXACT_MASS>
548.080841196

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.88827009428287

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid

> <ALOGPS_LOGP>
-1.09

> <JCHEM_LOGP>
-2.653509559666667

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1763386933118705

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7326140016891394

> <JCHEM_PKA_STRONGEST_BASIC>
-3.240344259094388

> <JCHEM_POLAR_SURFACE_AREA>
251.07999999999996

> <JCHEM_REFRACTIVITY>
107.7585

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.16e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dtdp-β-L-rhamnose

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006354
     RDKit          3D
Deoxythymidine diphosphate-L-rhamnose
 61 63  0  0  0  0  0  0  0  0999 V2000
   -6.4009    3.1354   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6691    1.7750    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6956    0.8031    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9497   -0.4500    0.4355 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8900   -1.4298    0.2688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5280   -1.5816   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0729   -2.0730   -1.0411 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1412   -3.4692   -0.8600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6666   -1.4050    0.2002 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6391   -0.3115   -0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5149   -0.9309   -0.6313 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7549   -0.8345    0.4863 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.6730   -2.3090    1.1334 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3367    0.1519    1.7598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2769   -0.6996   -0.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1911   -1.9366    0.6576 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.6659   -3.2523    0.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9204   -1.8426    2.3439 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247   -1.8181    0.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9888   -0.5865   -0.3714 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7102    0.3540    0.6469 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0769    1.6266    0.3381 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0354    2.1266    1.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6229    1.8352   -1.0296 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6058    1.6396   -1.9725 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7321    0.8779   -1.3681 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9511    1.3103   -0.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3558   -0.5065   -0.8801 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3027   -0.8272    0.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7360   -0.9627    0.8962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1440   -0.7471    0.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3679   -1.9005    1.3038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1452    0.1719    1.0732 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9147    1.4549    0.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7729    2.3361    0.7511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6354    3.9526    0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0332    3.2498   -1.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3260    3.2295   -0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7314    1.0781   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2250   -2.4049    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5244   -0.5937   -1.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1324   -2.3230   -1.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4464   -1.8268   -1.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6853   -3.6563    0.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1482   -2.2143    0.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0871    0.3093   -0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4686    0.3673    0.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1262    1.0606    1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0474   -2.7570    2.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2031   -0.5609   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1608    2.2894    0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0646    3.2077    1.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6307    1.7702    2.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0325    1.6600    1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9129    2.8998   -1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9950    1.3953   -2.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8434    0.8845   -2.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0038    2.3057   -0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5406   -1.2156   -1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1759   -1.7225    0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0705   -0.1091    1.4634 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
  9 30  1  0
  4 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 34 35  2  0
 34  2  1  0
 30  5  1  0
 28 20  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  5 40  1  1
  6 41  1  0
  6 42  1  0
  7 43  1  6
  8 44  1  0
  9 45  1  1
 10 46  1  0
 10 47  1  0
 14 48  1  0
 18 49  1  0
 20 50  1  6
 22 51  1  6
 23 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  1
 25 56  1  0
 26 57  1  6
 27 58  1  0
 28 59  1  6
 29 60  1  0
 33 61  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0    8658.3658664.129   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8655.6948668.747   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8658.3658670.287   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.8588666.437   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8663.9108662.967   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8666.1928665.669   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0    8667.5268666.437   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0    8669.2328665.463   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8666.7568667.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8668.2968667.770   0.000  0.00  0.00           O+0
HETATM   11  P   UNK     0    8670.9338666.445   0.000  0.00  0.00           P+0
HETATM   12  O   UNK     0    8672.2698665.673   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8670.1638667.777   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8671.7038667.777   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8674.9348664.137   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8677.6028665.673   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8674.9348670.291   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    8677.6028668.751   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    8674.9358668.754   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0    8673.6018667.984   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0    8673.6018666.444   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8674.9358665.674   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8676.2688666.444   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8676.2688667.984   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0    8662.2718666.592   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0    8661.0258665.686   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8661.5018664.222   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8663.0418664.222   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8663.5178665.686   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8658.3638668.748   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8657.0298667.978   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0    8657.0298666.437   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0    8658.3638665.668   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0    8659.6978666.437   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0    8659.6978667.978   0.000  0.00  0.00           C+0
CONECT    1   33                                                            
CONECT    2   31                                                            
CONECT    3   30                                                            
CONECT    4    6   29                                                       
CONECT    5   28                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7   11                                                       
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    8   12   13   14                                             
CONECT   12   11   21                                                       
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15   22                                                            
CONECT   16   23                                                            
CONECT   17   19                                                            
CONECT   18   24                                                            
CONECT   19   24   20   17                                                  
CONECT   20   19   21                                                       
CONECT   21   22   20   12                                                  
CONECT   22   21   23   15                                                  
CONECT   23   22   24   16                                                  
CONECT   24   19   23   18                                                  
CONECT   25   26   29                                                       
CONECT   26   27   25   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29    5                                                  
CONECT   29   28   25    4                                                  
CONECT   30   31   35    3                                                  
CONECT   31   30   32    2                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34    1                                                  
CONECT   34   33   35   26                                                  
CONECT   35   30   34                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

COMPND    HMDB0006354
HETATM    1  C1  UNL     1      -6.401   3.135  -0.324  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.669   1.775   0.147  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.696   0.803   0.040  1.00  0.00           C  
HETATM    4  N1  UNL     1      -5.950  -0.450   0.436  1.00  0.00           N  
HETATM    5  C4  UNL     1      -4.890  -1.430   0.269  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.528  -1.582  -1.182  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.073  -2.073  -1.041  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.141  -3.469  -0.860  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.667  -1.405   0.200  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.639  -0.311  -0.006  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.515  -0.931  -0.631  1.00  0.00           O  
HETATM   12  P1  UNL     1       0.755  -0.834   0.486  1.00  0.00           P  
HETATM   13  O3  UNL     1       0.673  -2.309   1.133  1.00  0.00           O  
HETATM   14  O4  UNL     1       0.337   0.152   1.760  1.00  0.00           O  
HETATM   15  O5  UNL     1       2.277  -0.700  -0.126  1.00  0.00           O  
HETATM   16  P2  UNL     1       3.191  -1.937   0.658  1.00  0.00           P  
HETATM   17  O6  UNL     1       2.666  -3.252   0.158  1.00  0.00           O  
HETATM   18  O7  UNL     1       2.920  -1.843   2.344  1.00  0.00           O  
HETATM   19  O8  UNL     1       4.825  -1.818   0.331  1.00  0.00           O  
HETATM   20  C9  UNL     1       4.989  -0.586  -0.371  1.00  0.00           C  
HETATM   21  O9  UNL     1       4.710   0.354   0.647  1.00  0.00           O  
HETATM   22  C10 UNL     1       5.077   1.627   0.338  1.00  0.00           C  
HETATM   23  C11 UNL     1       6.035   2.127   1.416  1.00  0.00           C  
HETATM   24  C12 UNL     1       5.623   1.835  -1.030  1.00  0.00           C  
HETATM   25  O10 UNL     1       4.606   1.640  -1.973  1.00  0.00           O  
HETATM   26  C13 UNL     1       6.732   0.878  -1.368  1.00  0.00           C  
HETATM   27  O11 UNL     1       7.951   1.310  -0.847  1.00  0.00           O  
HETATM   28  C14 UNL     1       6.356  -0.507  -0.880  1.00  0.00           C  
HETATM   29  O12 UNL     1       7.303  -0.827   0.119  1.00  0.00           O  
HETATM   30  O13 UNL     1      -3.736  -0.963   0.896  1.00  0.00           O  
HETATM   31  C15 UNL     1      -7.144  -0.747   0.937  1.00  0.00           C  
HETATM   32  O14 UNL     1      -7.368  -1.900   1.304  1.00  0.00           O  
HETATM   33  N2  UNL     1      -8.145   0.172   1.073  1.00  0.00           N  
HETATM   34  C16 UNL     1      -7.915   1.455   0.670  1.00  0.00           C  
HETATM   35  O15 UNL     1      -8.773   2.336   0.751  1.00  0.00           O  
HETATM   36  H1  UNL     1      -6.635   3.953   0.373  1.00  0.00           H  
HETATM   37  H2  UNL     1      -7.033   3.250  -1.261  1.00  0.00           H  
HETATM   38  H3  UNL     1      -5.326   3.230  -0.634  1.00  0.00           H  
HETATM   39  H4  UNL     1      -4.731   1.078  -0.410  1.00  0.00           H  
HETATM   40  H5  UNL     1      -5.225  -2.405   0.614  1.00  0.00           H  
HETATM   41  H6  UNL     1      -4.524  -0.594  -1.692  1.00  0.00           H  
HETATM   42  H7  UNL     1      -5.132  -2.323  -1.687  1.00  0.00           H  
HETATM   43  H8  UNL     1      -2.446  -1.827  -1.895  1.00  0.00           H  
HETATM   44  H9  UNL     1      -2.685  -3.656   0.018  1.00  0.00           H  
HETATM   45  H10 UNL     1      -2.148  -2.214   0.858  1.00  0.00           H  
HETATM   46  H11 UNL     1      -2.087   0.309  -0.888  1.00  0.00           H  
HETATM   47  H12 UNL     1      -1.469   0.367   0.761  1.00  0.00           H  
HETATM   48  H13 UNL     1       0.126   1.061   1.573  1.00  0.00           H  
HETATM   49  H14 UNL     1       3.047  -2.757   2.663  1.00  0.00           H  
HETATM   50  H15 UNL     1       4.203  -0.561  -1.124  1.00  0.00           H  
HETATM   51  H16 UNL     1       4.161   2.289   0.431  1.00  0.00           H  
HETATM   52  H17 UNL     1       6.065   3.208   1.438  1.00  0.00           H  
HETATM   53  H18 UNL     1       5.631   1.770   2.408  1.00  0.00           H  
HETATM   54  H19 UNL     1       7.033   1.660   1.301  1.00  0.00           H  
HETATM   55  H20 UNL     1       5.913   2.900  -1.114  1.00  0.00           H  
HETATM   56  H21 UNL     1       4.995   1.395  -2.846  1.00  0.00           H  
HETATM   57  H22 UNL     1       6.843   0.885  -2.472  1.00  0.00           H  
HETATM   58  H23 UNL     1       8.004   2.306  -0.943  1.00  0.00           H  
HETATM   59  H24 UNL     1       6.541  -1.216  -1.689  1.00  0.00           H  
HETATM   60  H25 UNL     1       7.176  -1.723   0.501  1.00  0.00           H  
HETATM   61  H26 UNL     1      -9.070  -0.109   1.463  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3    3   34
CONECT    3    4   39
CONECT    4    5   31
CONECT    5    6   30   40
CONECT    6    7   41   42
CONECT    7    8    9   43
CONECT    8   44
CONECT    9   10   30   45
CONECT   10   11   46   47
CONECT   11   12
CONECT   12   13   13   14   15
CONECT   14   48
CONECT   15   16
CONECT   16   17   17   18   19
CONECT   18   49
CONECT   19   20
CONECT   20   21   28   50
CONECT   21   22
CONECT   22   23   24   51
CONECT   23   52   53   54
CONECT   24   25   26   55
CONECT   25   56
CONECT   26   27   28   57
CONECT   27   58
CONECT   28   29   59
CONECT   29   60
CONECT   31   32   32   33
CONECT   33   34   61
CONECT   34   35   35
END

HMDB0006354
     RDKit          3D
Deoxythymidine diphosphate-L-rhamnose
 61 63  0  0  0  0  0  0  0  0999 V2000
   -6.4009    3.1354   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6691    1.7750    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6956    0.8031    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9497   -0.4500    0.4355 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8900   -1.4298    0.2688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5280   -1.5816   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0729   -2.0730   -1.0411 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1412   -3.4692   -0.8600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6666   -1.4050    0.2002 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6391   -0.3115   -0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5149   -0.9309   -0.6313 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7549   -0.8345    0.4863 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.6730   -2.3090    1.1334 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3367    0.1519    1.7598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2769   -0.6996   -0.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1911   -1.9366    0.6576 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.6659   -3.2523    0.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9204   -1.8426    2.3439 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247   -1.8181    0.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9888   -0.5865   -0.3714 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7102    0.3540    0.6469 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0769    1.6266    0.3381 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0354    2.1266    1.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6229    1.8352   -1.0296 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6058    1.6396   -1.9725 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7321    0.8779   -1.3681 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9511    1.3103   -0.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3558   -0.5065   -0.8801 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3027   -0.8272    0.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7360   -0.9627    0.8962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1440   -0.7471    0.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3679   -1.9005    1.3038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1452    0.1719    1.0732 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9147    1.4549    0.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7729    2.3361    0.7511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6354    3.9526    0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0332    3.2498   -1.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3260    3.2295   -0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7314    1.0781   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2250   -2.4049    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5244   -0.5937   -1.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1324   -2.3230   -1.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4464   -1.8268   -1.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6853   -3.6563    0.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1482   -2.2143    0.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0871    0.3093   -0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4686    0.3673    0.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1262    1.0606    1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0474   -2.7570    2.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2031   -0.5609   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1608    2.2894    0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0646    3.2077    1.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6307    1.7702    2.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0325    1.6600    1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9129    2.8998   -1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9950    1.3953   -2.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8434    0.8845   -2.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0038    2.3057   -0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5406   -1.2156   -1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1759   -1.7225    0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0705   -0.1091    1.4634 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
  9 30  1  0
  4 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 34 35  2  0
 34  2  1  0
 30  5  1  0
 28 20  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  5 40  1  1
  6 41  1  0
  6 42  1  0
  7 43  1  6
  8 44  1  0
  9 45  1  1
 10 46  1  0
 10 47  1  0
 14 48  1  0
 18 49  1  0
 20 50  1  6
 22 51  1  6
 23 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  1
 25 56  1  0
 26 57  1  6
 27 58  1  0
 28 59  1  6
 29 60  1  0
 33 61  1  0
M  END

Synonyms

Value	Source
dTDP-6-Deoxy-beta-L-mannose	ChEBI
dTDP-6-Deoxy-L-mannose	ChEBI
dTDP-L-Rhamnose	ChEBI
Thymidine 5'-(trihydrogen diphosphate), p'-(6-deoxy-beta-L-mannopyranosyl) ester	ChEBI
Thymidine diphosphate-L-rhamnose	ChEBI
dTDP-beta-L-Rhamnose	Kegg
dTDP-6-Deoxy-b-L-mannose	Generator
dTDP-6-Deoxy-β-L-mannose	Generator
Thymidine 5'-(trihydrogen diphosphate), p'-(6-deoxy-b-L-mannopyranosyl) ester	Generator
Thymidine 5'-(trihydrogen diphosphate), p'-(6-deoxy-β-L-mannopyranosyl) ester	Generator
Thymidine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-b-L-mannopyranosyl) ester	Generator
Thymidine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-beta-L-mannopyranosyl) ester	Generator
Thymidine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-β-L-mannopyranosyl) ester	Generator
Thymidine diphosphoric acid-L-rhamnose	Generator
dTDP-b-L-Rhamnose	Generator
dTDP-Β-L-rhamnose	Generator
Deoxythymidine diphosphoric acid-L-rhamnose	Generator
Thymidine diphosphate rhamnose	HMDB
Deoxythymidine diphosphate rhamnose	HMDB
TDP-L-Rhamnose	HMDB
TDP-Rhamnose	HMDB
dTDP L-Rhamnose	HMDB
Deoxythymidine diphosphate-L-rhamnose	HMDB

Molecular Formula

C₁₆H₂₆N₂O₁₅P₂

Average Mass

548.3296

Monoisotopic Mass

548.080841196

IUPAC Name

{[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid

Traditional Name

dtdp-β-L-rhamnose

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H](C[C@@H]2O)N2C=C(C)C(=O)NC2=O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C16H26N2O15P2/c1-6-4-18(16(24)17-14(6)23)10-3-8(19)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(20)7(2)30-15/h4,7-13,15,19-22H,3,5H2,1-2H3,(H,25,26)(H,27,28)(H,17,23,24)/t7-,8-,9+,10+,11-,12+,13+,15+/m0/s1

InChI Key

ZOSQFDVXNQFKBY-CGAXJHMRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pentose phosphate
Monosaccharide phosphate
Organic pyrophosphate
Pyrimidone
Monoalkyl phosphate
Hydroxypyrimidine
Oxane
Monosaccharide
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Organic phosphoric acid derivative
Hydropyrimidine
Tetrahydrofuran
Heteroaromatic compound
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic nitrogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dTDP-L-rhamnose (CHEBI:15774 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	11.6 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-2.7	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	251.08 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	107.76 m³·mol⁻¹	ChemAxon
Polarizability	45.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Deoxythymidine diphosphate-L-rhamnose,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_17) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-43e353abbd92638144fe	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-3911000000-cdabd033d59b1aef7f01	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-3900000000-8f759174f3f6aab6d0e7	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udj-3502490000-5d4d8fa9a27e2cafec77	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fb9-3905010000-e8b50977df37869f1701	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-4901000000-b718aeb0ca866d681e90	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0101090000-cd1c8b30ff72e832534a	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9743230000-d289a67be04016b75045	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9710000000-d43e2745a51f03a29aa3	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000090000-946e334068a1f247b670	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9102210000-d4c75b5cc9c1e379626b	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-2209000000-9ed146b1b9e4293acc01	2021-09-25	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

Cytoplasm

Biospecimen Locations

Not Available

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0014145	dTDP-beta-L-rhamnose	dTDP-4-dehydro-beta-L-rhamnose	dTDP-4-dehydrorhamnose reductase	Reduction	RHEA	34755880
MMDBr0015346	dTDP-6-deoxy-beta-L-talose	dTDP-beta-L-rhamnose	dTDP-L-rhamnose 4-epimerase	Epimerization	RHEA	34755880
MMDBr0015349	dTDP-beta-L-rhamnose	alpha-L-rhamnosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octa-cis-decaprenol	N-acetylglucosaminyl-diphospho-decaprenol L-rhamnosyltransferase	Transfer of a rhamnosyl group	RHEA	34755880
MMDBr0015873	8-Demethyltetracenomycin C	8-demethyl-8-alpha-L-rhamnosyl-tetracenomycin C	Elloramycin glycosyltransferase ElmGT	Glycosylation	RHEA	34755880
MMDBr0019344	Hydrogen Ion	NADP	dTDP-4-dehydrorhamnose reductase	Reduction	PathBank	31602464
MMDBr0025939	dTDP-beta-L-rhamnose	Hydrogen Ion	Protein-arginine rhamnosyltransferase	Transfer of a rhamnosyl group	RHEA	34755880
MMDBr0025940	dTDP-beta-L-rhamnose	Hydrogen Ion	Protein-arginine rhamnosyltransferase	Transfer of a rhamnosyl group	RHEA	34755880

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
Bacteria	Proteobacteria	7	Human ; Human subgingival plaque; Human saliva; Human feces; Human feces; pleural fluid plaque; bal; Human stool
Bacteria	Actinobacteria	5	Human
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

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

External Links

HMDB ID

HMDB0006354

DrugBank ID

DB03723

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

121966

PDB ID

Not Available

ChEBI ID

15774

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Giraud MF, Leonard GA, Field RA, Berlind C, Naismith JH: RmlC, the third enzyme of dTDP-L-rhamnose pathway, is a new class of epimerase. Nat Struct Biol. 2000 May;7(5):398-402. doi: 10.1038/75178. [PubMed:10802738 ]
Dong C, Beis K, Giraud MF, Blankenfeldt W, Allard S, Major LL, Kerr ID, Whitfield C, Naismith JH: A structural perspective on the enzymes that convert dTDP-d-glucose into dTDP-l-rhamnose. Biochem Soc Trans. 2003 Jun;31(Pt 3):532-6. doi: 10.1042/bst0310532. [PubMed:12773151 ]

Showing metabocard for dTDP-beta-L-rhamnose (MMDBc0054471)

MOL for #<Metabolite:0x00007f5a9980d5b8>

3D MOL for #<Metabolite:0x00007f5a9980d5b8>

3D SDF for #<Metabolite:0x00007f5a9980d5b8>

3D-SDF for #<Metabolite:0x00007f5a9980d5b8>

PDB for #<Metabolite:0x00007f5a9980d5b8>

3D PDB for #<Metabolite:0x00007f5a9980d5b8>

SMILES for #<Metabolite:0x00007f5a9980d5b8>

INCHI for #<Metabolite:0x00007f5a9980d5b8>

Structure for #<Metabolite:0x00007f5a9980d5b8>

3D Structure for #<Metabolite:0x00007f5a9980d5b8>