NP-MRD: Showing NP-Card for 3-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid (NP0249995)

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Record Information

Version

2.0

Created at

2022-09-07 12:42:52 UTC

Updated at

2022-09-07 12:42:52 UTC

NP-MRD ID

NP0249995

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid

Description

3-[6-O-(4-Hydroxy-trans-cinnamoyl)-beta-D-glucopyranosyloxy]-3-methylglutaric acid belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. 3-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid is found in Codonopsis pilosula. Based on a literature review very few articles have been published on 3-[6-O-(4-Hydroxy-trans-cinnamoyl)-beta-D-glucopyranosyloxy]-3-methylglutaric acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072214422D          

 33 34  0  0  1  0            999 V2000
    3.2704   -1.7605    0.0000 C   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
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    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
    2.4454   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -3.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  2 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  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
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END

     RDKit          3D

 59 60  0  0  0  0  0  0  0  0999 V2000
   -5.4657   -0.1516   -1.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7090    0.6235   -0.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6323    0.3926    0.4261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3430    1.0063    1.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4464    1.8335    1.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1131    0.6593    2.7984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5831    2.0123   -1.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8604    2.6555   -1.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9782    2.1574   -1.3481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8347    3.9942   -1.9363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5740   -0.0956   -0.6820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4882    0.0490    0.0298 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4335    0.2418   -0.8691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1853    0.1090   -0.3864 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7911    0.0997   -1.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277   -0.0362   -1.0938 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1621   -0.0596   -2.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8647    0.0425   -3.2295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5704   -0.2002   -1.5817 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8692   -0.3096   -0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2330   -0.4507    0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4864   -0.5640    1.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7662   -0.6950    2.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8494   -0.7190    1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1462   -0.8537    1.7045 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6334   -0.6089   -0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3204   -0.4766   -0.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0946   -1.0947    0.4571 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3866   -1.0719    0.9248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9470   -1.1206    1.5666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7384   -2.1777    2.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2640   -1.2489    0.8311 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2451   -1.4195    1.7786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1464   -1.2039   -1.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5323   -0.0365   -1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2204    0.3507   -2.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7287    0.5011    0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5972   -0.7579    0.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0402    0.2692    2.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9230    2.6545   -0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0227    2.0553   -2.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3674    4.7082   -1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3549    0.8512    0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0641    1.0051    0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7526    1.0636   -2.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5800   -0.6992   -2.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3176   -0.2081   -2.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0543   -0.2948    0.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6338   -0.5437    2.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9734   -0.7841    3.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6102    0.0188    1.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4343   -0.6200   -0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1909   -0.3925   -1.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021   -1.9996   -0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8643   -1.8636    0.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9416   -0.1338    2.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2205   -2.4349    2.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470   -2.1158    0.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9322   -1.9120    2.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  6  1  0
  4  5  2  0
  2  7  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  2 11  1  0
 11 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  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 14 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 12  1  0
 27 21  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
 10 42  1  0
 12 43  1  1
 14 44  1  1
 15 45  1  0
 15 46  1  0
 19 47  1  0
 20 48  1  0
 22 49  1  0
 23 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  6
 29 55  1  0
 30 56  1  1
 31 57  1  0
 32 58  1  6
 33 59  1  0
M  END


  Mrv1652309072214422D          

 33 34  0  0  1  0            999 V2000
    3.2704   -1.7605    0.0000 C   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
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    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
    2.4454   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -3.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  2 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  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
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0249995

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC(O)=O)(CC(O)=O)O[C@@H]1O[C@H](COC(=O)\C=C\C2=CC=C(O)C=C2)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O12/c1-21(8-14(23)24,9-15(25)26)33-20-19(30)18(29)17(28)13(32-20)10-31-16(27)7-4-11-2-5-12(22)6-3-11/h2-7,13,17-20,22,28-30H,8-10H2,1H3,(H,23,24)(H,25,26)/b7-4+/t13-,17-,18+,19-,20+/m1/s1

> <INCHI_KEY>
JUWZKCKHYLBOCZ-LKVOICQTSA-N

> <FORMULA>
C21H26O12

> <MOLECULAR_WEIGHT>
470.427

> <EXACT_MASS>
470.142426277

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.11409677740507

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid

> <JCHEM_LOGP>
0.21124850966666647

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.191625815116151

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5204904579818947

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490927159486564

> <JCHEM_POLAR_SURFACE_AREA>
200.27999999999997

> <JCHEM_REFRACTIVITY>
108.09960000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic 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       6.105  -3.286   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.565  -5.954   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.025  -5.954   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.255  -4.620   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.255  -7.287   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.337 -18.480   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003 -19.250   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.003 -20.790   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13   32                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   21                                                       
CONECT   28   14   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   12   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Value	Source
3-[6-O-(4-Hydroxy-trans-cinnamoyl)-b-D-glucopyranosyloxy]-3-methylglutarate	Generator
3-[6-O-(4-Hydroxy-trans-cinnamoyl)-b-D-glucopyranosyloxy]-3-methylglutaric acid	Generator
3-[6-O-(4-Hydroxy-trans-cinnamoyl)-beta-D-glucopyranosyloxy]-3-methylglutarate	Generator
3-[6-O-(4-Hydroxy-trans-cinnamoyl)-β-D-glucopyranosyloxy]-3-methylglutarate	Generator
3-[6-O-(4-Hydroxy-trans-cinnamoyl)-β-D-glucopyranosyloxy]-3-methylglutaric acid	Generator

Chemical Formula

C₂₁H₂₆O₁₂

Average Mass

470.4270 Da

Monoisotopic Mass

470.14243 Da

IUPAC Name

3-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid

Traditional Name

3-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid

CAS Registry Number

Not Available

SMILES

CC(CC(O)=O)(CC(O)=O)O[C@@H]1O[C@H](COC(=O)\C=C\C2=CC=C(O)C=C2)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H26O12/c1-21(8-14(23)24,9-15(25)26)33-20-19(30)18(29)17(28)13(32-20)10-31-16(27)7-4-11-2-5-12(22)6-3-11/h2-7,13,17-20,22,28-30H,8-10H2,1H3,(H,23,24)(H,25,26)/b7-4+/t13-,17-,18+,19-,20+/m1/s1

InChI Key

JUWZKCKHYLBOCZ-LKVOICQTSA-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
Codonopsis pilosula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
O-glycosyl compound
Glycosyl compound
Tricarboxylic acid or derivatives
Styrene
Sugar acid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Carboxylic acid
Acetal
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Alcohol
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	0.21	ChemAxon
pKa (Strongest Acidic)	3.52	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	200.28 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	108.1 m³·mol⁻¹	ChemAxon
Polarizability	45.11 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

102522668

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid (NP0249995)

MOL for NP0249995 (3-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid)

3D MOL for NP0249995 (3-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid)

3D SDF for NP0249995 (3-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid)

3D-SDF for NP0249995 (3-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid)

PDB for NP0249995 (3-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid)

3D PDB for NP0249995 (3-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid)

SMILES for NP0249995 (3-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid)

INCHI for NP0249995 (3-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid)

Structure for NP0249995 (3-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid)

3D Structure for NP0249995 (3-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}pentanedioic acid)