NP-MRD: Showing NP-Card for (2r)-n-[(2r,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-sulfanylpropanimidic acid (NP0267173)

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Record Information

Version

2.0

Created at

2022-09-08 11:52:08 UTC

Updated at

2022-09-08 11:52:08 UTC

NP-MRD ID

NP0267173

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-n-[(2r,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-sulfanylpropanimidic acid

Description

(2r)-n-[(2r,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-sulfanylpropanimidic acid is found in Apis cerana. (2r)-n-[(2r,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-sulfanylpropanimidic acid was first documented in 2002 (PMID: 11929223).

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv1533006041518452D          
 
 32 33  0  0  1  0            999 V2000
   17.6641   -9.9394    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.3776  -10.3542    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.0921   -9.9410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.0930   -9.1172    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.3796   -8.7065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.6651   -9.1155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8102  -10.7690    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.8102  -11.5945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.5273  -12.0093    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.2403  -11.5945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.2403  -10.7690    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.5273  -10.3583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9520  -10.3588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9520  -12.0087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0949  -12.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0949  -10.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5284  -12.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3749  -10.7607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3806   -7.8811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8070  -10.3567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3766  -11.1796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9502   -8.7041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8090   -8.7074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9465  -12.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6600  -13.2413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.3759  -12.8314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6590  -14.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0908  -13.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8068  -12.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0899  -14.0684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2335  -13.2385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9430  -14.4807    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  7 16  1  1  0  0  0
  3  4  1  0  0  0  0
  9 17  1  1  0  0  0
  4  5  1  0  0  0  0
 16 18  1  0  0  0  0
  1 13  1  1  0  0  0
  5  6  1  0  0  0  0
  5 19  1  1  0  0  0
  7  8  1  0  0  0  0
  3 20  1  1  0  0  0
  8  9  1  0  0  0  0
  2 21  1  1  0  0  0
  9 10  1  0  0  0  0
  6 22  1  6  0  0  0
 10 11  1  0  0  0  0
  4 23  1  6  0  0  0
 11 12  1  0  0  0  0
 14 24  1  0  0  0  0
 12  7  1  0  0  0  0
 24 25  1  0  0  0  0
  6  1  1  0  0  0  0
 25 26  1  0  0  0  0
 11 13  1  6  0  0  0
 25 27  1  1  0  0  0
 26 28  1  0  0  0  0
 10 14  1  6  0  0  0
 28 29  1  0  0  0  0
  1  2  1  0  0  0  0
 28 30  2  0  0  0  0
  8 15  1  6  0  0  0
 24 31  2  0  0  0  0
  2  3  1  0  0  0  0
 27 32  1  0  0  0  0
M  END

     RDKit          3D

 62 63  0  0  0  0  0  0  0  0999 V2000
    3.7740    4.6231    1.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6982    3.3518    1.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8259    3.4193   -0.0331 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4897    2.1045    1.8668 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4153    0.8550    1.0958 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5104   -0.0722    1.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5099   -1.6247    0.6456 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1121    0.2112    1.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3438    0.7526    2.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6444   -0.9138    0.5792 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3437   -1.5122    0.8054 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4963   -1.4321   -0.4941 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5976   -0.1101   -0.7790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8891    0.4130   -0.7265 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0656    1.3765    0.4140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9703    0.9075    1.3801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4196    2.7600    0.0503 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2712    3.5826   -0.0548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2795    2.9352   -1.1468 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4264    3.7135   -0.8815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7052    1.6252   -1.7902 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2972    1.9086   -3.0193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4087    0.8816   -2.0321 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5661    1.7192   -2.7341 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1750   -2.1762   -1.4502 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2572   -3.5156   -1.2444 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7336   -4.1618   -2.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0056   -3.6709   -1.9434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0613   -3.8861    0.1591 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3469   -5.2035    0.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967   -2.9547    1.2086 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1159   -3.1737    2.4491 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5091    5.3422    1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474    5.0891    1.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0463    4.4849    3.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3930    2.1066    2.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5699    1.1106    0.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4696    0.4813    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3418   -0.2937    2.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3449   -2.7494    1.4807 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2276   -1.3549   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1481   -0.9682    1.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -1.9490   -0.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5220   -0.4831   -0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814    1.4024    0.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2827   -0.0078    1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9807    3.2219    0.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5632    3.1688    0.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6804    3.4623   -1.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1972    3.0863   -0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3566    1.0208   -1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9356    2.6781   -2.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6417    0.0201   -2.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8180    1.6995   -3.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2854   -3.8963   -1.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6892   -5.2566   -2.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4574   -3.7897   -3.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6457   -4.3502   -2.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1823   -3.8959    0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9334   -5.5380   -0.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5756   -3.1683    1.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5326   -3.4065    3.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 31  1  0
 31 32  1  0
 31 29  1  0
 29 30  1  0
 29 26  1  0
 26 27  1  0
 27 28  1  0
 26 25  1  0
 25 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12 11  1  0
 23 14  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  6
  6 38  1  0
  6 39  1  0
  7 40  1  0
 10 41  1  0
 11 42  1  1
 31 61  1  1
 32 62  1  0
 29 59  1  6
 30 60  1  0
 26 55  1  6
 27 56  1  0
 27 57  1  0
 28 58  1  0
 12 43  1  1
 14 44  1  1
 15 45  1  1
 16 46  1  0
 17 47  1  1
 18 48  1  0
 19 49  1  6
 20 50  1  0
 21 51  1  1
 22 52  1  0
 23 53  1  6
 24 54  1  0
M  END

 
  Mrv1533006041518452D          
 
 32 33  0  0  1  0            999 V2000
   17.6641   -9.9394    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.3776  -10.3542    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.0921   -9.9410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.0930   -9.1172    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.3796   -8.7065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.6651   -9.1155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8102  -10.7690    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.8102  -11.5945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.5273  -12.0093    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.2403  -11.5945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.2403  -10.7690    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.5273  -10.3583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9520  -10.3588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9520  -12.0087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0949  -12.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0949  -10.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5284  -12.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3749  -10.7607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3806   -7.8811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8070  -10.3567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3766  -11.1796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9502   -8.7041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8090   -8.7074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9465  -12.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6600  -13.2413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.3759  -12.8314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6590  -14.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0908  -13.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8068  -12.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0899  -14.0684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2335  -13.2385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9430  -14.4807    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  7 16  1  1  0  0  0
  3  4  1  0  0  0  0
  9 17  1  1  0  0  0
  4  5  1  0  0  0  0
 16 18  1  0  0  0  0
  1 13  1  1  0  0  0
  5  6  1  0  0  0  0
  5 19  1  1  0  0  0
  7  8  1  0  0  0  0
  3 20  1  1  0  0  0
  8  9  1  0  0  0  0
  2 21  1  1  0  0  0
  9 10  1  0  0  0  0
  6 22  1  6  0  0  0
 10 11  1  0  0  0  0
  4 23  1  6  0  0  0
 11 12  1  0  0  0  0
 14 24  1  0  0  0  0
 12  7  1  0  0  0  0
 24 25  1  0  0  0  0
  6  1  1  0  0  0  0
 25 26  1  0  0  0  0
 11 13  1  6  0  0  0
 25 27  1  1  0  0  0
 26 28  1  0  0  0  0
 10 14  1  6  0  0  0
 28 29  1  0  0  0  0
  1  2  1  0  0  0  0
 28 30  2  0  0  0  0
  8 15  1  6  0  0  0
 24 31  2  0  0  0  0
  2  3  1  0  0  0  0
 27 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0267173

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N[C@@H](CS)C(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H30N2O12S/c1-4(21)18-5(3-32)16(29)19-7-9(23)8(22)6(2-20)30-17(7)31-15-13(27)11(25)10(24)12(26)14(15)28/h5-15,17,20,22-28,32H,2-3H2,1H3,(H,18,21)(H,19,29)/t5-,6+,7+,8+,9+,10-,11-,12+,13+,14+,15-,17+/m0/s1

> <INCHI_KEY>
MQBCDKMPXVYCGO-FQBKTPCVSA-N

> <FORMULA>
C17H30N2O12S

> <MOLECULAR_WEIGHT>
486.49

> <EXACT_MASS>
486.151945588

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.143698193443164

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-acetamido-3-sulfanylpropanamide

> <ALOGPS_LOGP>
-2.09

> <JCHEM_LOGP>
-6.328847519333333

> <ALOGPS_LOGS>
-1.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.784279572808476

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.952869585602679

> <JCHEM_PKA_STRONGEST_BASIC>
-3.645774271002643

> <JCHEM_POLAR_SURFACE_AREA>
238.49999999999997

> <JCHEM_REFRACTIVITY>
104.31329999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.76e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mycothiol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  C   UNK     0      32.973 -18.553   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      34.305 -19.328   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      35.639 -18.557   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      35.640 -17.019   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      34.309 -16.252   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.975 -17.016   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.646 -20.102   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.646 -21.643   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.984 -22.417   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.315 -21.643   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.315 -20.102   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      28.984 -19.335   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      31.644 -19.337   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      31.644 -22.416   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      26.310 -22.418   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      26.310 -19.335   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      28.986 -23.958   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      24.966 -20.087   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      34.310 -14.711   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      36.973 -19.332   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      34.303 -20.869   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      31.640 -16.248   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      36.977 -16.254   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      31.633 -23.951   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      32.965 -24.717   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      34.302 -23.952   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      32.963 -26.258   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      35.636 -24.720   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      36.973 -23.955   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      35.634 -26.261   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      30.303 -24.712   0.000  0.00  0.00           O+0
HETATM   32  S   UNK     0      31.627 -27.031   0.000  0.00  0.00           S+0
CONECT    1   13    6    2                                                  
CONECT    2   21    1    3                                                  
CONECT    3    4   20    2                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5   22    1                                                  
CONECT    7   16    8   12                                                  
CONECT    8    7    9   15                                                  
CONECT    9   17    8   10                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13    1   11                                                       
CONECT   14   24   10                                                       
CONECT   15    8                                                            
CONECT   16    7   18                                                       
CONECT   17    9                                                            
CONECT   18   16                                                            
CONECT   19    5                                                            
CONECT   20    3                                                            
CONECT   21    2                                                            
CONECT   22    6                                                            
CONECT   23    4                                                            
CONECT   24   14   25   31                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   28                                                       
CONECT   27   25   32                                                       
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   24                                                            
CONECT   32   27                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-Pentahydroxycyclohexyl 2-[(N-acetyl-L-cysteinyl)amino]-2-deoxy-alpha-D-glucopyranoside	ChEBI
1-D-Myo-inositol-2-(N-acetyl-L-cysteinyl)amino-2-deoxy-alpha-D-glucopyranoside	ChEBI
1-O-(2'-[N-Acetyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol	ChEBI
1-O-(2-[N-Acetyl-L-cysteinyl]amido-2-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol	ChEBI
1-O-[2-(N-Acetyl-L-cysteinamido)-2-deoxy-alpha-D-glucopyranosyl]-D-myo-inositol	ChEBI
1-O-[2-(N(2)-Acetyl-L-cysteinamido)-2-deoxy-alpha-D-glucopyranosyl]-1D-myo-inositol	ChEBI
1-O-[2-[[(2R)-2-(Acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-alpha-D-glucopyranosyl]-D-myo-inositol	ChEBI
1D-1-O-[2-(N-Acetyl-L-cysteinamido)-2-deoxy-alpha-D-glucopyranosyl]-myo-inositol	ChEBI
AcCys-GLCN-ins	ChEBI
MSH	ChEBI
(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-Pentahydroxycyclohexyl 2-[(N-acetyl-L-cysteinyl)amino]-2-deoxy-a-D-glucopyranoside	Generator
(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-Pentahydroxycyclohexyl 2-[(N-acetyl-L-cysteinyl)amino]-2-deoxy-α-D-glucopyranoside	Generator
1-D-Myo-inositol-2-(N-acetyl-L-cysteinyl)amino-2-deoxy-a-D-glucopyranoside	Generator
1-D-Myo-inositol-2-(N-acetyl-L-cysteinyl)amino-2-deoxy-α-D-glucopyranoside	Generator
1-O-(2'-[N-Acetyl-L-cysteinyl]amido-2'-deoxy-a-D-glucopyranosyl)-D-myo-inositol	Generator
1-O-(2'-[N-Acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol	Generator
1-O-(2-[N-Acetyl-L-cysteinyl]amido-2-deoxy-a-D-glucopyranosyl)-D-myo-inositol	Generator
1-O-(2-[N-Acetyl-L-cysteinyl]amido-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol	Generator
1-O-[2-(N-Acetyl-L-cysteinamido)-2-deoxy-a-D-glucopyranosyl]-D-myo-inositol	Generator
1-O-[2-(N-Acetyl-L-cysteinamido)-2-deoxy-α-D-glucopyranosyl]-D-myo-inositol	Generator
1-O-[2-(N(2)-Acetyl-L-cysteinamido)-2-deoxy-a-D-glucopyranosyl]-1D-myo-inositol	Generator
1-O-[2-(N(2)-Acetyl-L-cysteinamido)-2-deoxy-α-D-glucopyranosyl]-1D-myo-inositol	Generator
1-O-[2-[[(2R)-2-(Acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]-D-myo-inositol	Generator
1-O-[2-[[(2R)-2-(Acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-α-D-glucopyranosyl]-D-myo-inositol	Generator
1D-1-O-[2-(N-Acetyl-L-cysteinamido)-2-deoxy-a-D-glucopyranosyl]-myo-inositol	Generator
1D-1-O-[2-(N-Acetyl-L-cysteinamido)-2-deoxy-α-D-glucopyranosyl]-myo-inositol	Generator

Chemical Formula

C₁₇H₃₀N₂O₁₂S

Average Mass

486.4900 Da

Monoisotopic Mass

486.15195 Da

IUPAC Name

(2R)-N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-acetamido-3-sulfanylpropanamide

Traditional Name

mycothiol

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@@H](CS)C(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C17H30N2O12S/c1-4(21)18-5(3-32)16(29)19-7-9(23)8(22)6(2-20)30-17(7)31-15-13(27)11(25)10(24)12(26)14(15)28/h5-15,17,20,22-28,32H,2-3H2,1H3,(H,18,21)(H,19,29)/t5-,6+,7+,8+,9+,10-,11-,12+,13+,14+,15-,17+/m0/s1

InChI Key

MQBCDKMPXVYCGO-FQBKTPCVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acyl-alpha-hexosamines

Alternative Parents

Substituents

N-acyl-alpha-hexosamine
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Cysteine or derivatives
Glycosyl compound
O-glycosyl compound
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Cyclohexanol
Cyclitol or derivatives
Monosaccharide
Oxane
Cyclic alcohol
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Alkylthiol
Polyol
Primary alcohol
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organosulfur compound
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

thiol (CHEBI:16768 )
2-deoxy-alpha-D-glucoside (CHEBI:16768 )
mycothiols (CHEBI:16768 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.1	ALOGPS
logP	-6.3	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	9.95	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	238.5 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	104.31 m³·mol⁻¹	ChemAxon
Polarizability	46.14 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00028629

Chemspider ID

Not Available

KEGG Compound ID

C06717

BioCyc ID

CPD1G-2

BiGG ID

Not Available

Wikipedia Link

Mycothiol

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

16768

Good Scents ID

Not Available

References

General References

Nicholas GM, Kovac P, Bewley CA: Total synthesis and proof of structure of mycothiol bimane. J Am Chem Soc. 2002 Apr 10;124(14):3492-3. doi: 10.1021/ja017891a. [PubMed:11929223 ]
Vogt RN, Steenkamp DJ, Zheng R, Blanchard JS: The metabolism of nitrosothiols in the Mycobacteria: identification and characterization of S-nitrosomycothiol reductase. Biochem J. 2003 Sep 15;374(Pt 3):657-66. doi: 10.1042/BJ20030642. [PubMed:12809551 ]
Sareen D, Newton GL, Fahey RC, Buchmeier NA: Mycothiol is essential for growth of Mycobacterium tuberculosis Erdman. J Bacteriol. 2003 Nov;185(22):6736-40. doi: 10.1128/JB.185.22.6736-6740.2003. [PubMed:14594852 ]
Wang R, Yin YJ, Wang F, Li M, Feng J, Zhang HM, Zhang JP, Liu SJ, Chang WR: Crystal structures and site-directed mutagenesis of a mycothiol-dependent enzyme reveal a novel folding and molecular basis for mycothiol-mediated maleylpyruvate isomerization. J Biol Chem. 2007 Jun 1;282(22):16288-294. doi: 10.1074/jbc.M610347200. Epub 2007 Apr 11. [PubMed:17428791 ]
LOTUS database [Link]

Showing NP-Card for (2r)-n-[(2r,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-sulfanylpropanimidic acid (NP0267173)

MOL for NP0267173 ((2r)-n-[(2r,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-sulfanylpropanimidic acid)

3D MOL for NP0267173 ((2r)-n-[(2r,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-sulfanylpropanimidic acid)

3D SDF for NP0267173 ((2r)-n-[(2r,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-sulfanylpropanimidic acid)

3D-SDF for NP0267173 ((2r)-n-[(2r,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-sulfanylpropanimidic acid)

PDB for NP0267173 ((2r)-n-[(2r,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-sulfanylpropanimidic acid)

3D PDB for NP0267173 ((2r)-n-[(2r,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-sulfanylpropanimidic acid)

SMILES for NP0267173 ((2r)-n-[(2r,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-sulfanylpropanimidic acid)

INCHI for NP0267173 ((2r)-n-[(2r,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-sulfanylpropanimidic acid)

Structure for NP0267173 ((2r)-n-[(2r,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-sulfanylpropanimidic acid)

3D Structure for NP0267173 ((2r)-n-[(2r,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1s,2r,3r,4s,5s,6r)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]-2-[(1-hydroxyethylidene)amino]-3-sulfanylpropanimidic acid)