NP-MRD: Showing NP-Card for (-)-Saprosmoside B (NP0080295)

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Record Information

Version

2.0

Created at

2022-04-29 01:20:18 UTC

Updated at

2022-04-29 01:20:18 UTC

NP-MRD ID

NP0080295

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Saprosmoside B

Description

(1S,4aS,5R,7aS)-1-{[(2S,3R,4S,5S,6R)-3-[(1S,4aS,5R,7aS)-5-hydroxy-7-({[(methylsulfanyl)carbonyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carbonyloxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. (-)-Saprosmoside B is found in Saprosma scortechinii. Based on a literature review very few articles have been published on (1S,4aS,5R,7aS)-1-{[(2S,3R,4S,5S,6R)-3-[(1S,4aS,5R,7aS)-5-hydroxy-7-({[(methylsulfanyl)carbonyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carbonyloxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203202D          

 57 62  0  0  1  0            999 V2000
   -4.2868   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  1  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
   -2.8579   -4.1250    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
   -3.5724   -5.3625    0.0000 C   0  0  2  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
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   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   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5429   -6.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2775   -6.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6131   -5.5020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4201   -5.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0950   -6.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8400   -7.5672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3921   -8.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1990   -8.0088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1371   -8.9649    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6892   -9.5780    0.0000 C   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
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  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
    1.4289   -1.6500    0.0000 C   0  0  1  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
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   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
   -0.7846    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8465   -1.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    1.8646    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   -1.6500    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
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    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  6  0  0  0
  5  8  1  1  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  6  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 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
 28 33  1  0  0  0  0
 33 34  1  6  0  0  0
 35 34  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 35 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 37 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 36 46  1  6  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 44 49  1  1  0  0  0
 31 50  1  6  0  0  0
 50 51  1  0  0  0  0
 30 52  1  1  0  0  0
 29 53  1  6  0  0  0
  3 54  1  1  0  0  0
 54 55  1  0  0  0  0
  2 56  1  6  0  0  0
  1 57  1  1  0  0  0
M  END

     RDKit          3D

101106  0  0  0  0  0  0  0  0999 V2000
   -4.5594    1.7425    6.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3574    0.8459    5.0179 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3945    1.8084    3.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9201    2.9725    3.4215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9596    1.2730    2.3798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0553    1.9091    1.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7451    2.2980    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4077    3.5410    0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582    3.6386   -0.3179 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3652    4.6541    0.3456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4681    2.2776    0.0072 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4755    1.8813   -0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0721    2.1198   -0.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3238    2.6843    0.2417 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9041    1.7619   -1.7375 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2845    2.0153   -1.5257 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1071    0.7573   -1.4258 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1802    0.9112   -0.5456 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0747    0.0492    0.5605 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9851    0.8271    1.7170 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9979    0.9430    2.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1259    0.2803    2.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1849    0.4841    3.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9997    1.2649    4.4797 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3585   -0.1998    3.4051 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3709   -0.6415    1.3731 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7744   -1.9877    1.9628 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9614   -2.4332    1.3967 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6619   -2.8917    1.6402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7813   -2.3074    0.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5428   -2.9526    0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5338   -2.9941   -1.0688 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2074   -0.9144    0.5211 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5998    0.3857   -2.6566 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4344    1.2902   -3.2235 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8647    0.7981   -3.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9802   -0.4047   -3.9051 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3262    2.7022   -2.7035 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7719    3.5987   -3.6738 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8352    3.0015   -2.5054 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6486    4.3107   -2.0939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9038    1.2882   -2.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2825    1.1099   -2.1611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0372    0.6361   -1.0632 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7209   -0.7112   -0.9126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8213   -1.5475   -0.9720 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0053   -2.0722    0.2715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3977   -3.3637    0.3942 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2855   -4.3694    0.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8772   -5.6481    0.6916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3747   -3.7867   -0.6543 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5535   -3.0636   -0.4830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8855   -3.5337   -2.0599 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3916   -4.7387   -2.5529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7857   -2.5124   -2.1120 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9373   -1.8249   -3.3256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6330    1.3748    0.1945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2901    2.3710    6.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1214    1.0285    7.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7822    2.3988    5.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4929    1.1570    0.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7409    2.7661    1.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0561    4.4180    0.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0925    3.8676   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0533    4.3623    1.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224    2.4175    0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3531    2.5199   -0.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3966   -0.0274   -1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1254   -0.5185    0.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9091    1.6175    3.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9729   -0.0016    2.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2538   -0.2705    0.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8783   -1.9262    3.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8900   -2.3215    0.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6116   -3.9232    2.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5261   -4.0404    0.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6306   -2.4505    0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3526   -2.6212   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5869   -0.9348   -0.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1465    1.3631   -4.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2774    0.6419   -2.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4754    1.5711   -3.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1271   -0.2906   -4.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9096    2.8677   -1.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6255    4.5294   -3.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853    2.9129   -3.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2146    4.4616   -1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    0.9507   -2.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1120    0.8060   -1.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7022   -0.8587   -1.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9796   -3.4113    1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7136   -4.2233    1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5903   -4.4395   -0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4341   -5.6261    1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6340   -4.8553   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5907   -2.3275   -1.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
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 41 87  1  0
M  END


  Mrv1652304292203202D          

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  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  5  8  1  1  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
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 29 30  1  0  0  0  0
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 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  6  0  0  0
 35 34  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  2  0  0  0  0
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 35 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  2  0  0  0  0
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 37 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 36 46  1  6  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 44 49  1  1  0  0  0
 31 50  1  6  0  0  0
 50 51  1  0  0  0  0
 30 52  1  1  0  0  0
 29 53  1  6  0  0  0
  3 54  1  1  0  0  0
 54 55  1  0  0  0  0
  2 56  1  6  0  0  0
  1 57  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0080295

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC(=O)OCC1=C[C@@H](O)[C@H]2[C@@H]1[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC=C2C(=O)O[C@H]1[C@H](O[C@@H]2OC=C([C@H]3[C@H](O)C=C(CO)[C@@H]23)C(O)=O)O[C@H](CO)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C34H44O22S/c1-57-34(48)51-7-11-3-15(39)21-13(9-50-31(19(11)21)55-32-26(44)24(42)22(40)16(5-36)52-32)29(47)54-27-25(43)23(41)17(6-37)53-33(27)56-30-18-10(4-35)2-14(38)20(18)12(8-49-30)28(45)46/h2-3,8-9,14-27,30-33,35-44H,4-7H2,1H3,(H,45,46)/t14-,15-,16-,17-,18-,19-,20+,21+,22-,23-,24+,25+,26-,27-,30+,31+,32+,33+/m1/s1

> <INCHI_KEY>
VGQBMHXNJUYFRO-QUFQFPGFSA-N

> <FORMULA>
C34H44O22S

> <MOLECULAR_WEIGHT>
836.76

> <EXACT_MASS>
836.204494231

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
101

> <JCHEM_AVERAGE_POLARIZABILITY>
79.98118774905981

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aS,5R,7aS)-1-{[(2S,3R,4S,5S,6R)-3-[(1S,4aS,5R,7aS)-5-hydroxy-7-({[(methylsulfanyl)carbonyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carbonyloxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid

> <ALOGPS_LOGP>
-1.57

> <JCHEM_LOGP>
-4.780781551999999

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.083866303239168

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.113209533716651

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0439835007809224

> <JCHEM_POLAR_SURFACE_AREA>
347.58000000000004

> <JCHEM_REFRACTIVITY>
183.93060000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.01e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,5R,7aS)-1-{[(2S,3R,4S,5S,6R)-3-[(1S,4aS,5R,7aS)-5-hydroxy-7-({[(methylsulfanyl)carbonyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carbonyloxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.668 -11.550   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.013 -11.516   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.518 -11.677   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.144 -10.270   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.651  -9.950   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.044 -12.661   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.568 -14.125   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.599 -15.270   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.105 -14.950   0.000  0.00  0.00           O+0
HETATM   23  S   UNK     0      -2.123 -16.734   0.000  0.00  0.00           S+0
HETATM   24  C   UNK     0      -3.153 -17.879   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -1.465   2.016   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -1.941  -1.941   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -3.447  -2.261   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -1.941   3.481   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      -9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+0
CONECT    1    2    6   57                                                  
CONECT    2    1    3   56                                                  
CONECT    3    2    4   54                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   13   18                                                  
CONECT   18   17                                                            
CONECT   19   15   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   12   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30   53                                                  
CONECT   30   29   31   52                                                  
CONECT   31   30   32   50                                                  
CONECT   32   31   33                                                       
CONECT   33   32   28   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37   46                                                  
CONECT   37   36   38   44                                                  
CONECT   38   37   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
CONECT   41   38   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   37   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   45   36   47                                                  
CONECT   47   46   48                                                       
CONECT   48   47                                                            
CONECT   49   44                                                            
CONECT   50   31   51                                                       
CONECT   51   50                                                            
CONECT   52   30                                                            
CONECT   53   29                                                            
CONECT   54    3   55                                                       
CONECT   55   54                                                            
CONECT   56    2                                                            
CONECT   57    1                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  124    0
END

View in JSmol

Synonyms

Value	Source
(1S,4AS,5R,7as)-1-{[(2S,3R,4S,5S,6R)-3-[(1S,4as,5R,7as)-5-hydroxy-7-({[(methylsulfanyl)carbonyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,7ah-cyclopenta[c]pyran-4-carbonyloxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-7-(hydroxymethyl)-1H,4ah,5H,7ah-cyclopenta[c]pyran-4-carboxylate	Generator
(1S,4AS,5R,7as)-1-{[(2S,3R,4S,5S,6R)-3-[(1S,4as,5R,7as)-5-hydroxy-7-({[(methylsulphanyl)carbonyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,7ah-cyclopenta[c]pyran-4-carbonyloxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-7-(hydroxymethyl)-1H,4ah,5H,7ah-cyclopenta[c]pyran-4-carboxylate	Generator
(1S,4AS,5R,7as)-1-{[(2S,3R,4S,5S,6R)-3-[(1S,4as,5R,7as)-5-hydroxy-7-({[(methylsulphanyl)carbonyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,7ah-cyclopenta[c]pyran-4-carbonyloxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-7-(hydroxymethyl)-1H,4ah,5H,7ah-cyclopenta[c]pyran-4-carboxylic acid	Generator

Chemical Formula

C₃₄H₄₄O₂₂S

Average Mass

836.7600 Da

Monoisotopic Mass

836.20449 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CSC(=O)OCC1=C[C@@H](O)[C@H]2[C@@H]1[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC=C2C(=O)O[C@H]1[C@H](O[C@@H]2OC=C([C@H]3[C@H](O)C=C(CO)[C@@H]23)C(O)=O)O[C@H](CO)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C34H44O22S/c1-57-34(48)51-7-11-3-15(39)21-13(9-50-31(19(11)21)55-32-26(44)24(42)22(40)16(5-36)52-32)29(47)54-27-25(43)23(41)17(6-37)53-33(27)56-30-18-10(4-35)2-14(38)20(18)12(8-49-30)28(45)46/h2-3,8-9,14-27,30-33,35-44H,4-7H2,1H3,(H,45,46)/t14-,15-,16-,17-,18-,19-,20+,21+,22-,23-,24+,25+,26-,27-,30+,31+,32+,33+/m1/s1

InChI Key

VGQBMHXNJUYFRO-QUFQFPGFSA-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
Saprosma scortechinii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Saccharolipid
O-glycosyl compound
Iridoid-skeleton
Glycosyl compound
Monoterpenoid
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Monothioacetal
Secondary alcohol
Thiocarbonic acid derivative
Carbonic acid derivative
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Sulfenyl compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organosulfur compound
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-1.6	ALOGPS
logP	-4.8	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	347.58 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	183.93 m³·mol⁻¹	ChemAxon
Polarizability	79.98 Å³	ChemAxon
Number of Rings	6	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

162971981

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Saprosmoside B (NP0080295)

MOL for NP0080295 ((-)-Saprosmoside B)

3D MOL for NP0080295 ((-)-Saprosmoside B)

3D SDF for NP0080295 ((-)-Saprosmoside B)

3D-SDF for NP0080295 ((-)-Saprosmoside B)

PDB for NP0080295 ((-)-Saprosmoside B)

3D PDB for NP0080295 ((-)-Saprosmoside B)

SMILES for NP0080295 ((-)-Saprosmoside B)

INCHI for NP0080295 ((-)-Saprosmoside B)

Structure for NP0080295 ((-)-Saprosmoside B)

3D Structure for NP0080295 ((-)-Saprosmoside B)