NP-MRD: Showing NP-Card for (-)-Verbenabraside B (NP0072552)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 17:53:33 UTC

Updated at

2022-04-28 17:53:33 UTC

NP-MRD ID

NP0072552

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Verbenabraside B

Description

[(2R,3S,4S,5R,6R)-6-{[(3R,3aS,4S,5S,6aS)-4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-hexahydro-2H-cyclopenta[b]furan-3-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (-)-Verbenabraside B is found in Verbena brasiliensis. Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6R)-6-{[(3R,3aS,4S,5S,6aS)-4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-hexahydro-2H-cyclopenta[b]furan-3-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219532D          

 37 40  0  0  1  0            999 V2000
   -1.3168    1.7408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1238    1.9123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3788    2.6969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8267    3.3100    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0198    3.1385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7648    2.3539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0422    2.1823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4677    3.7516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0817    4.0946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1857    2.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4407    3.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2476    3.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7997    3.2115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5026    4.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3096    4.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5645    5.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3715    5.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6264    6.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0744    7.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2674    6.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0125    6.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3293    7.9192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619    0.9561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    0.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4062    0.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250    1.3543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1765    0.5584    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  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  8  1  6  0  0  0
  4  9  1  1  0  0  0
  3 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
  1 23  1  6  0  0  0
 23 24  1  0  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 29 28  1  6  0  0  0
 30 29  1  6  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 33  1  0  0  0  0
 32 34  1  1  0  0  0
 31 35  1  6  0  0  0
 35 36  1  0  0  0  0
 31 37  1  1  0  0  0
M  END

     RDKit          3D

 69 72  0  0  0  0  0  0  0  0999 V2000
   -7.2623    0.5736   -0.8355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8128    0.2060   -0.5182 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3663   -0.9811   -1.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1928   -0.5275   -2.1714 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1118   -1.4399   -2.1135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5638   -1.4065   -0.8228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8363   -2.3138   -0.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0211   -0.1447   -0.1680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8477    0.5958    0.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875   -0.2846    1.3944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1926    0.2787    2.0354 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9194   -0.4459    1.7110 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4347   -1.1782    2.7429 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4131   -2.2183    2.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5718   -1.8166    1.7166 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7169   -1.1824    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6803   -0.9045   -0.1280 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0317   -0.8099   -0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1520   -0.2022   -1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4055    0.1983   -1.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3783    0.8381   -3.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5214    1.2500   -3.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7480    1.0064   -3.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9435    1.3870   -3.6915 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8350    0.3726   -1.8778 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6469   -0.0182   -1.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2480   -1.9043    3.3958 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6605   -3.0067    4.1078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4508   -0.8669    4.2481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7034   -1.2784    4.6383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4416    0.4403    3.5026 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4016    1.3817    4.0896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6404    0.6061   -1.3022 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9219    1.3203   -0.9548 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4163    1.8561   -2.1444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7741    2.4270    0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8694    3.3566   -0.5170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9016   -0.0536   -0.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4905    0.4069   -1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3848    1.6522   -0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7765   -0.0002    0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2173   -1.2962   -1.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0835   -1.8041   -0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4390   -0.2025   -3.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7738   -0.4086    0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2107    1.4614    1.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1105    0.9028   -0.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0594    1.3043    1.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8931   -0.5557    3.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8978   -2.9545    1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6209   -2.8342    3.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9236   -1.0485    0.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2076    0.0136   -1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3994    1.0246   -3.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4716    1.7451   -4.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0209    1.8532   -4.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8000    0.1758   -1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6910   -0.5169   -0.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4092   -2.2147    2.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4245   -3.8719    3.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1824   -0.7350    5.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7511   -2.2657    4.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4828    0.8648    3.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651    1.7608    3.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9353    1.2355   -1.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0572    2.6141   -1.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4990    2.1437    1.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7727    2.9555    0.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1384    3.4839   -1.4684 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  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 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  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 13 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
  8 33  1  0
 33 34  1  0
 34 35  1  6
 34 36  1  0
 36 37  1  0
 34  2  1  0
 33  4  1  0
 31 11  1  0
 26 20  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  1
  3 42  1  0
  3 43  1  0
  4 44  1  6
  8 45  1  1
  9 46  1  0
  9 47  1  0
 11 48  1  6
 13 49  1  1
 14 50  1  0
 14 51  1  0
 18 52  1  0
 19 53  1  0
 21 54  1  0
 22 55  1  0
 24 56  1  0
 25 57  1  0
 26 58  1  0
 27 59  1  6
 28 60  1  0
 29 61  1  1
 30 62  1  0
 31 63  1  6
 32 64  1  0
 33 65  1  6
 35 66  1  0
 36 67  1  0
 36 68  1  0
 37 69  1  0
M  END


  Mrv1652304282219532D          

 37 40  0  0  1  0            999 V2000
   -1.3168    1.7408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1238    1.9123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3788    2.6969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8267    3.3100    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0198    3.1385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7648    2.3539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0422    2.1823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4677    3.7516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0817    4.0946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1857    2.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4407    3.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2476    3.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7997    3.2115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5026    4.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3096    4.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5645    5.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3715    5.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6264    6.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0744    7.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2674    6.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0125    6.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3293    7.9192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619    0.9561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    0.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4062    0.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250    1.3543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1765    0.5584    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  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  8  1  6  0  0  0
  4  9  1  1  0  0  0
  3 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
  1 23  1  6  0  0  0
 23 24  1  0  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 29 28  1  6  0  0  0
 30 29  1  6  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 33  1  0  0  0  0
 32 34  1  1  0  0  0
 31 35  1  6  0  0  0
 35 36  1  0  0  0  0
 31 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0072552

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@@H]2OC(=O)[C@@H](CO[C@@H]3O[C@H](COC(=O)\C=C\C4=CC=C(O)C=C4)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]2[C@]1(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O12/c1-12-8-16-19(25(12,33)11-26)15(23(32)36-16)9-35-24-22(31)21(30)20(29)17(37-24)10-34-18(28)7-4-13-2-5-14(27)6-3-13/h2-7,12,15-17,19-22,24,26-27,29-31,33H,8-11H2,1H3/b7-4+/t12-,15-,16-,17+,19-,20+,21-,22+,24+,25-/m0/s1

> <INCHI_KEY>
IWCWCYABXSEJSH-HKIYPJGUSA-N

> <FORMULA>
C25H32O12

> <MOLECULAR_WEIGHT>
524.519

> <EXACT_MASS>
524.18937647

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.702642980799794

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(3R,3aS,4S,5S,6aS)-4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-hexahydro-2H-cyclopenta[b]furan-3-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
-0.06

> <JCHEM_LOGP>
-0.534921750666667

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.188370542566659

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.397939053973014

> <JCHEM_PKA_STRONGEST_BASIC>
-3.081589750776436

> <JCHEM_POLAR_SURFACE_AREA>
192.43999999999997

> <JCHEM_REFRACTIVITY>
124.45559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(3R,3aS,4S,5S,6aS)-4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydro-3H-cyclopenta[b]furan-3-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -2.458   3.249   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.964   3.570   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.440   5.034   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.410   6.179   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.904   5.859   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.428   4.394   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.079   4.074   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.873   7.003   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.886   7.643   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.947   5.354   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.423   6.819   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -7.929   7.139   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -8.959   5.995   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -8.405   8.604   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.911   8.924   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.387  10.389   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -11.893  10.709   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -12.369  12.173   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -11.339  13.318   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.832  12.998   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -9.357  11.533   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -11.815  14.783   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.982   1.785   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.476   1.465   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.905  -1.246   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.445  -1.246   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.000  -2.492   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.374  -1.246   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.625   1.510   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.780   2.528   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       4.063   1.042   0.000  0.00  0.00           O+0
CONECT    1    2    6   23                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    4                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19                                                            
CONECT   23    1   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29   25   31                                                  
CONECT   31   30   32   35   37                                             
CONECT   32   31   33   34                                                  
CONECT   33   32   29                                                       
CONECT   34   32                                                            
CONECT   35   31   36                                                       
CONECT   36   35                                                            
CONECT   37   31                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5R,6R)-6-{[(3R,3as,4S,5S,6as)-4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-hexahydro-2H-cyclopenta[b]furan-3-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₅H₃₂O₁₂

Average Mass

524.5190 Da

Monoisotopic Mass

524.18938 Da

IUPAC Name

Traditional Name

[(2R,3S,4S,5R,6R)-6-{[(3R,3aS,4S,5S,6aS)-4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydro-3H-cyclopenta[b]furan-3-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@@H]2OC(=O)[C@@H](CO[C@@H]3O[C@H](COC(=O)\C=C\C4=CC=C(O)C=C4)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]2[C@]1(O)CO

InChI Identifier

InChI=1S/C25H32O12/c1-12-8-16-19(25(12,33)11-26)15(23(32)36-16)9-35-24-22(31)21(30)20(29)17(37-24)10-34-18(28)7-4-13-2-5-14(27)6-3-13/h2-7,12,15-17,19-22,24,26-27,29-31,33H,8-11H2,1H3/b7-4+/t12-,15-,16-,17+,19-,20+,21-,22+,24+,25-/m0/s1

InChI Key

IWCWCYABXSEJSH-HKIYPJGUSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Verbena brasiliensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Terpene lactone
Coumaric acid ester
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
Monoterpenoid
Bicyclic monoterpenoid
Aromatic monoterpenoid
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Gamma butyrolactone
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	-0.06	ALOGPS
logP	-0.53	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	124.46 m³·mol⁻¹	ChemAxon
Polarizability	52.7 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162821196

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Verbenabraside B (NP0072552)

MOL for NP0072552 ((-)-Verbenabraside B)

3D MOL for NP0072552 ((-)-Verbenabraside B)

3D SDF for NP0072552 ((-)-Verbenabraside B)

3D-SDF for NP0072552 ((-)-Verbenabraside B)

PDB for NP0072552 ((-)-Verbenabraside B)

3D PDB for NP0072552 ((-)-Verbenabraside B)

SMILES for NP0072552 ((-)-Verbenabraside B)

INCHI for NP0072552 ((-)-Verbenabraside B)

Structure for NP0072552 ((-)-Verbenabraside B)

3D Structure for NP0072552 ((-)-Verbenabraside B)