NP-MRD: Showing NP-Card for {[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid (NP0240208)

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Record Information

Version

1.0

Created at

2022-09-06 23:57:33 UTC

Updated at

2022-09-06 23:57:33 UTC

NP-MRD ID

NP0240208

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid

Description

2-{[2-Amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}-2-[3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]acetic acid belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. {[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid is found in Streptomyces tendae. 2-{[2-Amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}-2-[3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]acetic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171504432D          

 35 37  0  0  0  0            999 V2000
    6.2728   -4.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -3.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028   -3.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -2.4652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -3.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -4.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -2.7770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -2.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4803   -2.3797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1594   -1.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7830   -1.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7126   -0.2576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4894   -1.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2494   -1.1849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559   -1.4326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7921   -2.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0114   -1.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2511   -1.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0547   -0.8713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126   -0.4561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -0.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6799   -0.0409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -4.3361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -3.8684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3530   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -2.9329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -4.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7032   -4.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433   -4.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732   -5.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5133   -6.2071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -5.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -5.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  2  0  0  0  0
  8 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 29 35  1  0  0  0  0
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
    3.9684   -2.2317    1.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0956   -1.0182    1.2112 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6923   -1.4884    0.9069 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6309   -2.3244   -0.2517 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417   -0.3442    0.8109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6572    0.4978    1.7407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950   -0.1611   -0.3182 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133    0.9389   -0.4177 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7911    1.7557   -1.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1216    1.4602   -2.4166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5772    2.8572   -1.8816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4153    0.3699   -0.3544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3880    1.3313   -0.4406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4904    0.8202   -1.0667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6712    0.7661   -0.2258 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7099   -0.0294    0.8621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7985   -0.1246    1.6982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9073    0.6396    1.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9367    0.5894    2.1371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8625    1.4304    0.3142 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7803    1.4938   -0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7524    2.2506   -1.5045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1416   -0.4860   -1.6937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8793   -1.4958   -1.0941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6733   -0.6519   -1.4089 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8925   -0.4682   -2.5488 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6894   -0.2787    0.0155 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9720    0.8509   -0.2966 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875    0.1119    0.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3810    1.1909    1.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6770    1.5585    1.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7433    0.8504    0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0562    1.2231    1.2155 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4553   -0.2268    0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1653   -0.6081   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5175   -2.9396    2.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0079   -2.7865    0.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0845   -0.3289    2.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3764   -2.1129    1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9344   -1.8820   -1.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9458   -3.2911   -0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326   -0.8535   -1.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9030    1.5442    0.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3772    2.8554   -2.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079   -0.1154    0.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7418    1.5275   -1.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8116   -0.6259    1.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7705   -0.7919    2.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7049    2.0023    0.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3680   -0.5193   -2.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7739   -1.6018   -1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5230   -1.6651   -0.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5752   -1.3741   -2.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7261   -0.9224   -0.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867    1.0272   -1.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5263    1.7506    1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8916    2.4025    2.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2901   -0.8035   -0.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  5  7  1  0
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  8 12  1  0
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 13 14  1  0
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 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
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 21 22  2  0
  8  9  1  0
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  2 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
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 25 12  1  0
 21 15  1  0
 35 29  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  1
  3 40  1  1
  4 41  1  0
  4 42  1  0
  7 43  1  0
  8 44  1  1
 12 46  1  1
 14 47  1  6
 23 51  1  6
 24 52  1  0
 25 53  1  1
 26 54  1  0
 16 48  1  0
 17 49  1  0
 20 50  1  0
 11 45  1  0
 27 55  1  6
 28 56  1  0
 30 57  1  0
 31 58  1  0
 33 59  1  0
 34 60  1  0
 35 61  1  0
M  END


  Mrv1533004171504432D          

 35 37  0  0  0  0            999 V2000
    6.2728   -4.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -3.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028   -3.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -2.4652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -3.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -4.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -2.7770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -2.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4803   -2.3797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1594   -1.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7830   -1.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7126   -0.2576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4894   -1.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2494   -1.1849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559   -1.4326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7921   -2.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0114   -1.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2511   -1.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0547   -0.8713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126   -0.4561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -0.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6799   -0.0409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -4.3361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -3.8684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3530   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -2.9329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -4.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7032   -4.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433   -4.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732   -5.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5133   -6.2071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -5.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -5.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 14 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  2  0  0  0  0
  8 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 29 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0240208

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C(N)C(=O)NC(C1OC(C(O)C1O)N1C=CC(=O)NC1=O)C(O)=O)C(O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N4O10/c1-8(14(28)9-2-4-10(26)5-3-9)12(22)18(31)24-13(20(32)33)17-15(29)16(30)19(35-17)25-7-6-11(27)23-21(25)34/h2-8,12-17,19,26,28-30H,22H2,1H3,(H,24,31)(H,32,33)(H,23,27,34)

> <INCHI_KEY>
LQZKMASBFQOGJR-UHFFFAOYSA-N

> <FORMULA>
C21H26N4O10

> <MOLECULAR_WEIGHT>
494.457

> <EXACT_MASS>
494.164893053

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
46.550249156672585

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[2-amino-4-hydroxy-4-(4-hydroxyphenyl)-3-methylbutanamido]-2-[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid

> <ALOGPS_LOGP>
-0.12

> <JCHEM_LOGP>
-4.662176225010603

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.286424163571137

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1356468488673417

> <JCHEM_PKA_STRONGEST_BASIC>
7.948303616871299

> <JCHEM_POLAR_SURFACE_AREA>
231.97999999999996

> <JCHEM_REFRACTIVITY>
114.4396

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[2-amino-4-hydroxy-4-(4-hydroxyphenyl)-3-methylbutanamido][5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      11.709  -8.676   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.213  -7.221   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.205  -6.057   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      11.709  -4.602   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       9.693  -6.348   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.189  -7.803   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       8.685  -5.184   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.172  -5.475   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.164  -4.311   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.630  -4.442   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.031  -3.023   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.195  -2.015   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.064  -0.481   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.514  -2.811   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.932  -2.212   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       2.531  -2.674   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       1.479  -3.798   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.021  -3.449   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.469  -1.976   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.969  -1.627   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       0.584  -0.851   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.083  -1.201   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.136  -0.076   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.677  -8.094   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.156  -7.221   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      13.726  -6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.230  -5.475   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.734  -8.094   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.246  -7.803   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.254  -8.967   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.750 -10.422   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      17.758 -11.587   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      15.238 -10.713   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.230  -9.549   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    9   15                                                  
CONECT   15   14                                                            
CONECT   16   11   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   16   23                                                  
CONECT   23   22                                                            
CONECT   24    8   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    2   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   29                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
2-{[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}-2-[3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]acetate	Generator
Nikkomycin b	MeSH

Chemical Formula

C₂₁H₂₆N₄O₁₀

Average Mass

494.4570 Da

Monoisotopic Mass

494.16489 Da

IUPAC Name

2-[2-amino-4-hydroxy-4-(4-hydroxyphenyl)-3-methylbutanamido]-2-[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid

Traditional Name

[2-amino-4-hydroxy-4-(4-hydroxyphenyl)-3-methylbutanamido][5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid

CAS Registry Number

Not Available

SMILES

CC(C(N)C(=O)NC(C1OC(C(O)C1O)N1C=CC(=O)NC1=O)C(O)=O)C(O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C21H26N4O10/c1-8(14(28)9-2-4-10(26)5-3-9)12(22)18(31)24-13(20(32)33)17-15(29)16(30)19(35-17)25-7-6-11(27)23-21(25)34/h2-8,12-17,19,26,28-30H,22H2,1H3,(H,24,31)(H,32,33)(H,23,27,34)

InChI Key

LQZKMASBFQOGJR-UHFFFAOYSA-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
Streptomyces tendae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
5'-deoxyribonucleoside
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Glycosyl compound
N-glycosyl compound
Alpha-amino acid or derivatives
Phenylpropane
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyrimidone
Aralkylamine
Monocyclic benzene moiety
Fatty amide
Hydropyrimidine
N-acyl-amine
Pyrimidine
Benzenoid
Fatty acyl
Vinylogous amide
Tetrahydrofuran
1,3-aminoalcohol
Heteroaromatic compound
Secondary carboxylic acid amide
Amino acid or derivatives
Urea
Secondary alcohol
Carboxamide group
Lactam
Amino acid
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Carboxylic acid
Primary amine
Organic oxide
Organopnictogen compound
Alcohol
Organic nitrogen compound
Aromatic alcohol
Carbonyl group
Primary aliphatic amine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Amine
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.12	ALOGPS
logP	-4.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.14	ChemAxon
pKa (Strongest Basic)	7.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	231.98 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	114.44 m³·mol⁻¹	ChemAxon
Polarizability	46.55 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156814

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid (NP0240208)

MOL for NP0240208 ({[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid)

3D MOL for NP0240208 ({[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid)

3D SDF for NP0240208 ({[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid)

3D-SDF for NP0240208 ({[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid)

PDB for NP0240208 ({[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid)

3D PDB for NP0240208 ({[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid)

SMILES for NP0240208 ({[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid)

INCHI for NP0240208 ({[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid)

Structure for NP0240208 ({[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid)

3D Structure for NP0240208 ({[2-amino-1,4-dihydroxy-4-(4-hydroxyphenyl)-3-methylbutylidene]amino}[3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]acetic acid)