NP-MRD: Showing NP-Card for (2s)-1-{[(3r,3as,4s,9as,9bs)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid (NP0322435)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 01:11:53 UTC

Updated at

2022-09-12 01:11:53 UTC

NP-MRD ID

NP0322435

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-1-{[(3r,3as,4s,9as,9bs)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid

Description

(2S)-1-{[(3R,3aS,4S,9aS,9bS)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (2s)-1-{[(3r,3as,4s,9as,9bs)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid is found in Cichorium endivia. Based on a literature review very few articles have been published on (2S)-1-{[(3R,3aS,4S,9aS,9bS)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122203112D          

 38 42  0  0  1  0            999 V2000
    3.6754    3.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    2.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749    2.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    0.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0503    0.2365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.8326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8746    1.8326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4201    1.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    0.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    2.1877    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1007    2.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8386    2.2732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737    1.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895    1.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1585    2.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    2.6532    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6938    3.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4618    3.7704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0488    3.9834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    2.4776    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5438    3.2819    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8988    3.7963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217    4.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897    4.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    5.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997    5.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    6.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    7.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456    7.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686    8.3896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906    7.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    6.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    3.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  7  1  6  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 15  1  1  0  0  0
 11 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  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
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 37  1  0  0  0  0
 26 38  1  0  0  0  0
  2 38  1  0  0  0  0
M  END

     RDKit          3D

 69 73  0  0  0  0  0  0  0  0999 V2000
    1.6840    4.6951   -0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7045    3.6824   -0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5684    4.0151   -0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673    5.2232   -0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3412    6.1644    0.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5145    5.0914    0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9079    3.9544   -0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3477    3.5782   -0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1899    4.5762   -0.0558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7724    3.1986   -0.9528 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6297    1.7856   -0.4832 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6471    1.5563    0.5095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0795    0.9288    1.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4822    0.8976    2.8108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8549    0.2937    1.1029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2088   -0.9177    0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8547   -1.8950    1.1310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1696   -1.7087    1.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9060   -3.0246    1.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7831   -4.0461    1.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6013   -3.2558    0.8299 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5565   -3.6082   -0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418   -2.7556   -1.4849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3024   -4.9154   -0.9628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3842    1.4814    0.2730 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8829    1.3399   -0.4229 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1947    0.1064   -1.0115 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3315   -0.6379   -0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0907   -0.1511    0.1737 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6026   -1.9402   -1.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8761   -2.4696   -0.8007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -2.1116   -1.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2768   -2.5587   -0.9759 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3254   -3.3854    0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5358   -3.8635    0.6137 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1680   -3.7627    0.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9461   -3.2920    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1533    2.4108   -1.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5319    5.6838   -0.9041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6992    4.3555   -0.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7879    4.7505    0.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1569    5.8820    0.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6044    2.6668   -0.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6800    3.4960   -1.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9500    4.6714    0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7988    3.1726   -2.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823    1.1173   -1.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1242    0.0484    1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9139   -0.6900   -0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3527   -1.4193   -0.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6591   -0.8693    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2281   -1.6644    2.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3484   -2.9938    0.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6555   -3.2721    2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0361   -4.9045    0.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6191   -4.3573    2.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6741   -3.6447    1.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7085   -5.7191   -0.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3166    2.3138    1.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7177    1.5183    0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7895   -2.6675   -1.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7413   -1.7541   -2.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0450   -1.4572   -2.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1936   -2.2758   -1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0319   -3.3175    1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2366   -4.4117    1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0540   -3.5876    0.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2364    2.4612   -1.6278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284    2.1889   -2.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 24  1  0
 22 23  2  0
 15 25  1  0
 25 26  1  0
 26 38  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 34 36  1  0
 36 37  2  0
 10  7  1  0
  7  8  1  0
  8  9  1  0
  7  6  2  0
  6  4  1  0
  4  5  2  0
 38  2  1  0
 37 31  1  0
  4  3  1  0
 25 11  1  0
 21 17  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
 10 46  1  6
 11 47  1  6
 15 48  1  1
 16 49  1  0
 16 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  1
 24 58  1  0
 25 59  1  1
 26 60  1  1
 38 68  1  0
 38 69  1  0
 30 61  1  0
 30 62  1  0
 32 63  1  0
 33 64  1  0
 35 65  1  0
 36 66  1  0
 37 67  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
  6 42  1  0
M  END


  Mrv1652309122203112D          

 38 42  0  0  1  0            999 V2000
    3.6754    3.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    2.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749    2.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    0.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0503    0.2365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.8326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8746    1.8326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4201    1.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    0.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    2.1877    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1007    2.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8386    2.2732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737    1.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895    1.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1585    2.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    2.6532    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6938    3.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4618    3.7704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0488    3.9834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    2.4776    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5438    3.2819    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8988    3.7963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217    4.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897    4.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    5.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997    5.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    6.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    7.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456    7.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686    8.3896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906    7.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    6.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    3.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  7  1  6  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 15  1  1  0  0  0
 11 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  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
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 37  1  0  0  0  0
 26 38  1  0  0  0  0
  2 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322435

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2[C@@H]([C@@H]3OC(=O)[C@@H](CN4CCC[C@H]4C(O)=O)[C@H]3[C@H](C1)OC(=O)CC1=CC=C(O)C=C1)C(CO)=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H31NO9/c1-14-9-21(37-22(33)10-15-4-6-17(31)7-5-15)25-18(12-29-8-2-3-19(29)27(34)35)28(36)38-26(25)24-16(13-30)11-20(32)23(14)24/h4-7,11,18-19,21,24-26,30-31H,2-3,8-10,12-13H2,1H3,(H,34,35)/t18-,19-,21-,24-,25-,26-/m0/s1

> <INCHI_KEY>
CQBJKIZHLSYGOO-WOFYCZPASA-N

> <FORMULA>
C28H31NO9

> <MOLECULAR_WEIGHT>
525.554

> <EXACT_MASS>
525.199881582

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.71725272000414

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-{[(3R,3aS,4S,9aS,9bS)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid

> <JCHEM_LOGP>
-1.3942078481939293

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.722937807664866

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.078215750125917

> <JCHEM_PKA_STRONGEST_BASIC>
9.105499000924986

> <JCHEM_POLAR_SURFACE_AREA>
150.67

> <JCHEM_REFRACTIVITY>
134.78839999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-{[(3R,3aS,4S,9aS,9bS)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       6.861   7.086   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.657   6.126   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.999   4.625   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.441   4.084   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.726   4.932   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.372   2.545   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.888   2.136   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.346   0.694   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.827   0.442   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.039   3.421   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.499   3.421   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.651   2.136   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.166   2.545   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.038   1.585   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.097   4.084   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.188   4.932   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -1.565   4.243   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -1.818   2.724   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.340   2.495   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.029   3.872   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.932   4.953   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.162   6.475   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.595   7.038   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.958   7.436   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.539   4.625   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.882   6.126   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.678   7.086   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.907   8.609   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.341   9.172   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.703   9.569   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.933  11.092   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.271  12.052   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.042  13.575   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.392  14.138   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.621  15.661   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.596  13.178   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.366  11.655   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.269   6.794   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10   12   25                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   15   11   26                                                  
CONECT   26   25   27   38                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   31                                                       
CONECT   38   26    2                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
(2S)-1-{[(3R,3as,4S,9as,9BS)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-2H,3H,3ah,4H,5H,7H,9ah,9BH-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylate	Generator

Chemical Formula

C₂₈H₃₁NO₉

Average Mass

525.5540 Da

Monoisotopic Mass

525.19988 Da

IUPAC Name

(2S)-1-{[(3R,3aS,4S,9aS,9bS)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-{[(3R,3aS,4S,9aS,9bS)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=C2[C@@H]([C@@H]3OC(=O)[C@@H](CN4CCC[C@H]4C(O)=O)[C@H]3[C@H](C1)OC(=O)CC1=CC=C(O)C=C1)C(CO)=CC2=O

InChI Identifier

InChI=1S/C28H31NO9/c1-14-9-21(37-22(33)10-15-4-6-17(31)7-5-15)25-18(12-29-8-2-3-19(29)27(34)35)28(36)38-26(25)24-16(13-30)11-20(32)23(14)24/h4-7,11,18-19,21,24-26,30-31H,2-3,8-10,12-13H2,1H3,(H,34,35)/t18-,19-,21-,24-,25-,26-/m0/s1

InChI Key

CQBJKIZHLSYGOO-WOFYCZPASA-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
Cichorium endivia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline and derivatives

Alternative Parents

Substituents

Proline or derivatives
Alpha-amino acid
L-alpha-amino acid
Tricarboxylic acid or derivatives
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Gamma butyrolactone
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Amino acid
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid
Oxacycle
Azacycle
Organoheterocyclic compound
Primary alcohol
Organic oxide
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Organopnictogen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-1.4	ChemAxon
pKa (Strongest Acidic)	1.08	ChemAxon
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	150.67 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	134.79 m³·mol⁻¹	ChemAxon
Polarizability	53.72 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

163035371

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-1-{[(3r,3as,4s,9as,9bs)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid (NP0322435)

MOL for NP0322435 ((2s)-1-{[(3r,3as,4s,9as,9bs)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid)

3D MOL for NP0322435 ((2s)-1-{[(3r,3as,4s,9as,9bs)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid)

3D SDF for NP0322435 ((2s)-1-{[(3r,3as,4s,9as,9bs)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid)

3D-SDF for NP0322435 ((2s)-1-{[(3r,3as,4s,9as,9bs)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid)

PDB for NP0322435 ((2s)-1-{[(3r,3as,4s,9as,9bs)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid)

3D PDB for NP0322435 ((2s)-1-{[(3r,3as,4s,9as,9bs)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid)

SMILES for NP0322435 ((2s)-1-{[(3r,3as,4s,9as,9bs)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid)

INCHI for NP0322435 ((2s)-1-{[(3r,3as,4s,9as,9bs)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid)

Structure for NP0322435 ((2s)-1-{[(3r,3as,4s,9as,9bs)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid)

3D Structure for NP0322435 ((2s)-1-{[(3r,3as,4s,9as,9bs)-9-(hydroxymethyl)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-6-methyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-3-yl]methyl}pyrrolidine-2-carboxylic acid)