NP-MRD: Showing NP-Card for 4-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentanoic acid (NP0329998)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 14:56:32 UTC

Updated at

2022-09-12 14:56:32 UTC

NP-MRD ID

NP0329998

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

4-{[5-Hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentanoic acid belongs to the class of organic compounds known as glycosyl-amino acids. Glycosyl-amino acids are compounds consisting of saccharide linked through a glycosyl linkage (O-, N-, or S-) to an amino acid. 4-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentanoic acid is found in Ascochyta pisi. 4-{[5-Hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241504402D          

 32 33  0  0  0  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
    0.0000   -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  0  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
    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  0  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 O   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  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  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  0  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  0  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
  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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  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
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 63 64  0  0  0  0  0  0  0  0999 V2000
    2.9963   -2.5400   -2.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7675   -1.2163   -1.7181 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5449   -0.7389   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9564   -0.3368    0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570   -0.3873    0.5402 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5964    0.1378   -0.4099 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9015    1.6109   -0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    2.3889   -1.4507 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186    1.9305   -2.8377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792    1.0136   -3.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957    2.5480   -3.7938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7829   -0.0702    0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8068    0.3594   -0.6807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0190    0.0887   -0.0207 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7514   -0.8524   -0.7806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8296   -1.2392   -0.0164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4754   -2.5168   -0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5492   -2.8006    0.3432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8146   -0.0859   -0.0142 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0148    0.2783   -1.3481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1342    1.0364    0.7619 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9692    2.1559    0.8340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322    1.3447    0.0945 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0900    2.2596    0.8440 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445    0.1783    1.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1079   -0.4220    1.6935 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9591   -1.6402    2.3710 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9628    0.4515    2.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2957    0.6073    3.8046 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8170   -0.6923    0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0167   -0.6827   -0.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5585   -0.6284   -1.8999 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8176   -3.2419   -1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2384   -2.8086   -2.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0288   -2.6988   -2.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751   -0.8483    1.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566   -0.3164   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9659    1.7722   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8799    2.1033    0.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3923    3.4641   -1.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0151    2.4515   -1.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547    1.9830   -4.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8530    0.5244    1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9179   -1.1523    0.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8394   -0.3927    0.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4836   -1.3728    1.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7513   -3.3295   -0.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8488   -2.3984   -1.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2491   -3.2182    1.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7399   -0.3473    0.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8693    0.7304   -1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9347    0.6459    1.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4831    2.9382    0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9622    1.7585   -0.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8084    1.8889    1.7134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606    0.0185    2.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681    1.2847    1.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8489   -2.1056    2.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8914   -0.1206    2.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1742    1.4308    2.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7467    1.4145    3.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6330    0.0746    0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3759   -1.6721    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4 25  1  0
 25 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  1  0
 26 30  1  0
 30 31  1  0
 31 32  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 31  3  1  0
 23 14  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 25 56  1  0
 25 57  1  0
 27 58  1  0
 28 59  1  0
 28 60  1  0
 29 61  1  0
 30 62  1  0
 30 63  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  1
 16 46  1  1
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  1
 20 51  1  0
 21 52  1  1
 22 53  1  0
 23 54  1  6
 24 55  1  0
M  END


  Mrv1533004241504402D          

 32 33  0  0  0  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
    0.0000   -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  0  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
    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  0  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 O   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  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  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  0  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  0  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
  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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  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
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329998

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(CC(O)(CO)CC1=O)NC(CCC(O)=O)COC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H31NO12/c1-30-17-10(4-19(29,8-22)5-11(17)23)20-9(2-3-13(24)25)7-31-18-16(28)15(27)14(26)12(6-21)32-18/h9,12,14-16,18,20-22,26-29H,2-8H2,1H3,(H,24,25)

> <INCHI_KEY>
LELNPYJXQDAQQF-UHFFFAOYSA-N

> <FORMULA>
C19H31NO12

> <MOLECULAR_WEIGHT>
465.452

> <EXACT_MASS>
465.184625442

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
44.95708671430499

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.15

> <JCHEM_LOGP>
-4.418619123333333

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.177017883407066

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9442517856502612

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083417718179

> <JCHEM_POLAR_SURFACE_AREA>
215.46999999999994

> <JCHEM_REFRACTIVITY>
106.10630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.21e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         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  C   UNK     0       0.000 -10.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.344 -12.730   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.324 -12.730   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.797 -14.177   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001  -8.470   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       1.334  -8.470   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.002  -1.540   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8   10                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10    3   12                                                  
CONECT   12   11                                                            
CONECT   13    4   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   14   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₁₉H₃₁NO₁₂

Average Mass

465.4520 Da

Monoisotopic Mass

465.18463 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(CC(O)(CO)CC1=O)NC(CCC(O)=O)COC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C19H31NO12/c1-30-17-10(4-19(29,8-22)5-11(17)23)20-9(2-3-13(24)25)7-31-18-16(28)15(27)14(26)12(6-21)32-18/h9,12,14-16,18,20-22,26-29H,2-8H2,1H3,(H,24,25)

InChI Key

LELNPYJXQDAQQF-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
Ascochyta pisi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosyl-amino acids. Glycosyl-amino acids are compounds consisting of saccharide linked through a glycosyl linkage (O-, N-, or S-) to an amino acid.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glycosyl-amino acids

Alternative Parents

Substituents

Glycosyl-amino-acid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Gamma amino acid or derivatives
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Amino fatty acid
Sugar acid
Cyclohexenone
Heterocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Oxane
Monosaccharide
Vinylogous amide
Tertiary alcohol
Cyclic ketone
Secondary alcohol
Amino acid
Ketone
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Secondary aliphatic amine
Enamine
Secondary amine
Acetal
Polyol
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Amine
Organic oxide
Hydrocarbon derivative
Carbonyl group
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
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	-2.2	ALOGPS
logP	-4.4	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	215.47 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	106.11 m³·mol⁻¹	ChemAxon
Polarizability	44.96 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentanoic acid (NP0329998)

MOL for NP0329998 (4-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentanoic acid)

3D MOL for NP0329998 (4-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentanoic acid)

3D SDF for NP0329998 (4-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentanoic acid)

3D-SDF for NP0329998 (4-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentanoic acid)

PDB for NP0329998 (4-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentanoic acid)

3D PDB for NP0329998 (4-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentanoic acid)

SMILES for NP0329998 (4-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentanoic acid)

INCHI for NP0329998 (4-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentanoic acid)

Structure for NP0329998 (4-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentanoic acid)

3D Structure for NP0329998 (4-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pentanoic acid)