NP-MRD: Showing NP-Card for (4r)-4-{[(5r)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2r,3s,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid (NP0254570)

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Record Information

Version

2.0

Created at

2022-09-07 18:46:43 UTC

Updated at

2022-09-07 18:46:43 UTC

NP-MRD ID

NP0254570

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r)-4-{[(5r)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2r,3s,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid

Description

(4R)-4-{[(5R)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. (4r)-4-{[(5r)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2r,3s,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid is found in Ascochyta fabae. Based on a literature review very few articles have been published on (4R)-4-{[(5R)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072220462D          

 32 33  0  0  1  0            999 V2000
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1842   -6.8195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448   -6.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9626   -7.5947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
  4 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END

     RDKit          3D

 64 65  0  0  0  0  0  0  0  0999 V2000
    3.1877    4.9248    1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5282    4.1979    1.3215 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5880    4.5462    0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4416    5.8497    0.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0879    1.1730   -0.0490 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4613    1.6586    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5467    0.9948   -0.2148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0290   -0.1476    0.2424 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2607   -1.1350   -0.9105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0767   -1.2428   -1.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8070   -0.0758   -2.5043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4179   -2.3783   -0.3185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3945   -2.4666    0.6129 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2568   -3.5205    0.2695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2110   -1.2541    0.8574 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3381   -1.2788    0.0102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5025    0.0426    0.7616 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4846    0.7583    1.9529 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2911   -0.0531    0.5437 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145   -0.6238    0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0493   -0.8887   -0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2561   -0.6254   -1.9075 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8191   -0.6827   -3.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4010   -1.4728   -1.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0365   -1.2848   -2.0460 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9005   -2.2749    0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7942   -1.3882    1.3572 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2039   -2.1529    2.4710 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8248   -0.2851    1.2012 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0612   -0.9235    0.9903 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4257   -0.8853    1.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0983    6.0806   -0.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3699    3.8804    0.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5243    3.5676   -1.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6670    2.2084    1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417    1.8585    0.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1444    1.2299   -1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5356    2.6708   -0.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045    2.0541    1.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139   -0.6911    1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1942   -0.8980   -1.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3384   -2.0604   -2.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -1.6479   -1.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3292   -0.2814   -3.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9192   -2.7951    1.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7708   -4.2791   -0.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6374   -1.3399    1.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4977   -2.1791   -0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9543    0.7028   -0.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6899    1.7211    1.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3331   -0.6090    1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2360   -1.6717   -3.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6485    0.0679   -3.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0267   -0.4838   -3.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2582   -3.1430    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9712   -2.5394    0.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6129    0.3156    0.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4712   -0.6595    0.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8337   -1.5548    2.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
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 21  7  1  0
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 11 12  1  0
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 33 64  1  0
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 31 60  1  0
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 28 57  1  0
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 21 53  1  0
  7 39  1  6
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  4 34  1  0
  2  1  1  0
  8 40  1  0
  8 41  1  0
 10 42  1  1
 19 51  1  6
 20 52  1  0
 17 49  1  1
 18 50  1  0
 15 47  1  1
 16 48  1  0
 11 43  1  6
 12 44  1  0
 12 45  1  0
 13 46  1  0
M  END


  Mrv1652309072220462D          

 32 33  0  0  1  0            999 V2000
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1842   -6.8195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448   -6.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9626   -7.5947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
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 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
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 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
  4 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0254570

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C[C@](O)(CO)CC1=O)N[C@H](CCC(O)=N)CO[C@H]1[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]1CO

> <INCHI_IDENTIFIER>
InChI=1S/C19H32N2O11/c1-30-16-10(4-19(29,8-23)5-11(16)24)21-9(2-3-13(20)25)7-31-17-12(6-22)32-18(28)15(27)14(17)26/h9,12,14-15,17-18,21-23,26-29H,2-8H2,1H3,(H2,20,25)/t9-,12-,14-,15-,17-,18+,19-/m1/s1

> <INCHI_KEY>
WWWNCXCUDMPGJY-LAVMAAOOSA-N

> <FORMULA>
C19H32N2O11

> <MOLECULAR_WEIGHT>
464.468

> <EXACT_MASS>
464.200609858

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
45.980418462544904

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R)-4-{[(5R)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid

> <JCHEM_LOGP>
-7.050862059648266

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.276243925584557

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.554442842721441

> <JCHEM_PKA_STRONGEST_BASIC>
12.950928359096377

> <JCHEM_POLAR_SURFACE_AREA>
222.24999999999997

> <JCHEM_REFRACTIVITY>
118.86509999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-{[(5R)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.334  -8.470   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -2.667  -4.620   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.002  -1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.000 -10.780   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.344 -12.730   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.324 -12.730   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.797 -14.177   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.001  -8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23                                                            
CONECT   25    4   26                                                       
CONECT   26   25   27   28   30                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   26   31                                                       
CONECT   31   30    3   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Value	Source
(4R)-4-{[(5R)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidate	Generator

Chemical Formula

C₁₉H₃₂N₂O₁₁

Average Mass

464.4680 Da

Monoisotopic Mass

464.20061 Da

IUPAC Name

(4R)-4-{[(5R)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid

Traditional Name

(4R)-4-{[(5R)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid

CAS Registry Number

Not Available

SMILES

COC1=C(C[C@](O)(CO)CC1=O)N[C@H](CCC(O)=N)CO[C@H]1[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]1CO

InChI Identifier

InChI=1S/C19H32N2O11/c1-30-16-10(4-19(29,8-23)5-11(16)24)21-9(2-3-13(20)25)7-31-17-12(6-22)32-18(28)15(27)14(17)26/h9,12,14-15,17-18,21-23,26-29H,2-8H2,1H3,(H2,20,25)/t9-,12-,14-,15-,17-,18+,19-/m1/s1

InChI Key

WWWNCXCUDMPGJY-LAVMAAOOSA-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
Ascochyta fabae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Cyclohexenone
Oxane
Tertiary alcohol
Vinylogous amide
Hemiacetal
Ketone
Secondary alcohol
Cyclic ketone
Carboximidic acid
Carboximidic acid derivative
Dialkyl ether
Secondary aliphatic amine
Enamine
Ether
Oxacycle
Organoheterocyclic compound
Polyol
Secondary amine
Amine
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organopnictogen compound
Organic oxide
Primary alcohol
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	-7.1	ChemAxon
pKa (Strongest Acidic)	-0.55	ChemAxon
pKa (Strongest Basic)	12.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	222.25 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	118.87 m³·mol⁻¹	ChemAxon
Polarizability	45.98 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

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

163024288

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4r)-4-{[(5r)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2r,3s,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid (NP0254570)

MOL for NP0254570 ((4r)-4-{[(5r)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2r,3s,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid)

3D MOL for NP0254570 ((4r)-4-{[(5r)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2r,3s,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid)

3D SDF for NP0254570 ((4r)-4-{[(5r)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2r,3s,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid)

3D-SDF for NP0254570 ((4r)-4-{[(5r)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2r,3s,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid)

PDB for NP0254570 ((4r)-4-{[(5r)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2r,3s,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid)

3D PDB for NP0254570 ((4r)-4-{[(5r)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2r,3s,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid)

SMILES for NP0254570 ((4r)-4-{[(5r)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2r,3s,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid)

INCHI for NP0254570 ((4r)-4-{[(5r)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2r,3s,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid)

Structure for NP0254570 ((4r)-4-{[(5r)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2r,3s,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid)

3D Structure for NP0254570 ((4r)-4-{[(5r)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[(2r,3s,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}pentanimidic acid)