NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate (NP0149502)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 05:24:03 UTC

Updated at

2022-09-02 05:24:03 UTC

NP-MRD ID

NP0149502

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate

Description

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate is found in Gentiana macrophylla.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272007362D          

 39 42  0  0  0  0            999 V2000
10003.108910001.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.818910001.9251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.269110003.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.269110001.5163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.689010000.6964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.527910006.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.527910005.6077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.527910008.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.811210007.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.908710007.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.378410008.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.955810008.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.241410007.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.241210006.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.955610006.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.383210008.0857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.668710007.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.668710006.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.383210006.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.097610006.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.097610007.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.813110006.8448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.385210004.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.670310003.9569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.385210007.6702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.953410006.8448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.953410005.1943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.383810006.8452    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.669810006.4328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.669810005.6083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.383810005.1962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.097710005.6083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.097710006.4328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.689010003.1608    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.974210002.7481    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.974210001.9226    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.689010001.5100    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.403810001.9226    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.403810002.7481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  6  7  2  0  0  0  0
  8  9  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  6 14  1  0  0  0  0
 13  8  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 21 10  1  0  0  0  0
 21 11  1  0  0  0  0
 17 12  2  0  0  0  0
 15 18  2  0  0  0  0
 23 24  1  0  0  0  0
 28 29  1  0  0  0  0
 28 33  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
 31 23  1  6  0  0  0
 30 27  1  1  0  0  0
 29 26  1  6  0  0  0
 28 25  1  1  0  0  0
  6 22  1  0  0  0  0
 33 22  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 34 39  1  0  0  0  0
 38 39  1  0  0  0  0
 34 24  1  6  0  0  0
 38  1  1  6  0  0  0
 37  5  1  1  0  0  0
 36  4  1  6  0  0  0
 35  3  1  1  0  0  0
M  END

     RDKit          3D

 73 76  0  0  0  0  0  0  0  0999 V2000
    3.6221   -0.5661   -3.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2452   -0.2623   -1.7795 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1722   -0.2054   -0.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5016   -0.4542   -1.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4627   -0.4025   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359   -0.0984    1.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6928    0.1459    1.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7460    0.0963    0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3483    0.3549    0.8065 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0055    0.6292    1.9952 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3470    0.3235   -0.1326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0220    0.5742    0.1386 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8078   -0.5392   -0.1641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1473   -0.1506    0.1812 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9149   -1.4126    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1657   -1.3595    0.8747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2355   -0.8896    0.2472 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7585    0.1793    1.0348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6419    0.9239    0.2536 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8719    2.2420    0.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4154    1.9765    2.2117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9121    0.1047    0.1403 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.3801    0.1410   -1.1651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6970   -1.3102    0.6331 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9005   -1.3943    2.0151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3948   -1.9034    0.2231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4745   -2.3974   -1.0696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6877    0.7085   -0.9169 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5736    1.6835   -0.4940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5484    1.4289   -1.6506 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0886    0.7000   -2.7369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4299    1.7674   -0.6912 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7630    2.8121    0.1518 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0648   -0.0571    2.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3272   -0.2886    2.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8071   -0.6119    0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3638   -2.0523    0.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9224    0.3277    0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7772   -0.6365   -0.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8290   -0.3042   -3.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5030    0.0757   -3.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9467   -1.6238   -3.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8612   -0.6922   -2.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4393    0.3757    2.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089    0.8016    1.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0379    0.4617    1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3176   -1.9742    1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7604   -2.1186   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1519   -0.4805   -0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2258    1.0295   -0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5338    2.9201    0.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8686    2.6868    1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4127    2.0909    2.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6592    0.5742    0.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8451   -0.4326   -1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5154   -1.9240    0.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1537   -1.0002    2.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1590   -2.7280    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6771   -2.8956   -1.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1528    0.0845   -1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3593    1.9826    0.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9637    2.3801   -2.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4305    1.0216   -3.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4248    2.1238   -1.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0572    3.1977    0.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7192    0.1833    3.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0249   -0.2323    2.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5163   -2.7670    0.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0270   -2.2270   -0.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8519   -2.2622    1.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4946    1.2553   -0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4952   -0.1892   -0.5625 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6324    0.4796    1.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  7  1  0
  7  6  2  0
  6 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
 36 39  1  0
 39  5  1  0
  5  4  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 14 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
  4  3  1  0
 32 12  1  0
  5  6  1  0
 26 17  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  7 44  1  0
 34 66  1  0
 35 67  1  0
 37 68  1  0
 37 69  1  0
 37 70  1  0
 38 71  1  0
 38 72  1  0
 38 73  1  0
  4 43  1  0
 12 45  1  1
 14 46  1  1
 15 47  1  0
 15 48  1  0
 17 49  1  6
 19 50  1  6
 20 51  1  0
 20 52  1  0
 21 53  1  0
 22 54  1  1
 23 55  1  0
 24 56  1  6
 25 57  1  0
 26 58  1  1
 27 59  1  0
 28 60  1  6
 29 61  1  0
 30 62  1  6
 31 63  1  0
 32 64  1  6
 33 65  1  0
M  END


  Mrv1652309272007362D          

 39 42  0  0  0  0            999 V2000
10003.108910001.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.818910001.9251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.269110003.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.269110001.5163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.689010000.6964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.527910006.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.527910005.6077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.527910008.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.811210007.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.908710007.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.378410008.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.955810008.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.241410007.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.241210006.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.955610006.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.383210008.0857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.668710007.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.668710006.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.383210006.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.097610006.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.097610007.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.813110006.8448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.385210004.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.670310003.9569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.385210007.6702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.953410006.8448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.953410005.1943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.383810006.8452    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.669810006.4328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.669810005.6083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.383810005.1962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.097710005.6083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.097710006.4328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.689010003.1608    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.974210002.7481    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.974210001.9226    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.689010001.5100    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.403810001.9226    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.403810002.7481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  6  7  2  0  0  0  0
  8  9  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  6 14  1  0  0  0  0
 13  8  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 21 10  1  0  0  0  0
 21 11  1  0  0  0  0
 17 12  2  0  0  0  0
 15 18  2  0  0  0  0
 23 24  1  0  0  0  0
 28 29  1  0  0  0  0
 28 33  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
 31 23  1  6  0  0  0
 30 27  1  1  0  0  0
 29 26  1  6  0  0  0
 28 25  1  1  0  0  0
  6 22  1  0  0  0  0
 33 22  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 34 39  1  0  0  0  0
 38 39  1  0  0  0  0
 34 24  1  6  0  0  0
 38  1  1  6  0  0  0
 37  5  1  1  0  0  0
 36  4  1  6  0  0  0
 35  3  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0149502

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C=C2C=CC(C)(C)OC2=C1)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O14/c1-25(2)5-4-10-6-11(13(34-3)7-12(10)39-25)22(33)38-24-21(32)19(30)17(28)15(37-24)9-35-23-20(31)18(29)16(27)14(8-26)36-23/h4-7,14-21,23-24,26-32H,8-9H2,1-3H3/t14-,15-,16-,17-,18+,19+,20-,21-,23-,24+/m1/s1

> <INCHI_KEY>
BKABLXWGRDWHDB-GWOWOUNZSA-N

> <FORMULA>
C25H34O14

> <MOLECULAR_WEIGHT>
558.533

> <EXACT_MASS>
558.194855775

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
55.36629628073448

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethyl-2H-chromene-6-carboxylate

> <ALOGPS_LOGP>
-0.56

> <JCHEM_LOGP>
-1.4651228786666668

> <ALOGPS_LOGS>
-2.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.426161754681559

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.903045667851698

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083422322401

> <JCHEM_POLAR_SURFACE_AREA>
214.05999999999997

> <JCHEM_REFRACTIVITY>
129.01529999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8672.4708669.497   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8673.7958670.260   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8667.1698672.558   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8667.1698669.497   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8669.8198667.967   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8675.1198678.675   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8675.1198677.134   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8675.1198681.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8673.7818680.992   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8683.2968680.730   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8682.3068682.444   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8677.7848681.760   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8676.4518680.989   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8676.4508679.450   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8677.7848678.680   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8680.4498681.760   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8679.1158680.990   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8679.1158679.450   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8680.4498678.680   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8681.7828679.450   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8681.7828680.990   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8673.7848679.444   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0    8671.1198674.821   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8669.7858674.053   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0    8671.1198680.984   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0    8668.4468679.444   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0    8668.4468676.363   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0    8671.1168679.444   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8669.7848678.674   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8669.7848677.135   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8671.1168676.366   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0    8672.4498677.135   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0    8672.4498678.674   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8669.8198672.567   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8668.4858671.796   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8668.4858670.256   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0    8669.8198669.485   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0    8671.1548670.256   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0    8671.1548671.796   0.000  0.00  0.00           O+0
CONECT    1    2   38                                                       
CONECT    2    1                                                            
CONECT    3   35                                                            
CONECT    4   36                                                            
CONECT    5   37                                                            
CONECT    6    7   14   22                                                  
CONECT    7    6                                                            
CONECT    8    9   13                                                       
CONECT    9    8                                                            
CONECT   10   21                                                            
CONECT   11   21                                                            
CONECT   12   13   17                                                       
CONECT   13   12   14    8                                                  
CONECT   14   13   15    6                                                  
CONECT   15   14   18                                                       
CONECT   16   17   21                                                       
CONECT   17   18   16   12                                                  
CONECT   18   17   19   15                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16   10   11                                             
CONECT   22    6   33                                                       
CONECT   23   24   31                                                       
CONECT   24   23   34                                                       
CONECT   25   28                                                            
CONECT   26   29                                                            
CONECT   27   30                                                            
CONECT   28   29   33   25                                                  
CONECT   29   28   30   26                                                  
CONECT   30   29   31   27                                                  
CONECT   31   30   32   23                                                  
CONECT   32   31   33                                                       
CONECT   33   28   32   22                                                  
CONECT   34   35   39   24                                                  
CONECT   35   34   36    3                                                  
CONECT   36   35   37    4                                                  
CONECT   37   36   38    5                                                  
CONECT   38   37   39    1                                                  
CONECT   39   34   38                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
Gentiobiosyl 2,2-dimethyl-7-methoxy-2H-1-benzopyran-6-carboxylate	PhytoBank

Chemical Formula

C₂₅H₃₄O₁₄

Average Mass

558.5330 Da

Monoisotopic Mass

558.19486 Da

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethyl-2H-chromene-6-carboxylate

Traditional Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate

CAS Registry Number

Not Available

SMILES

COC1=C(C=C2C=CC(C)(C)OC2=C1)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C25H34O14/c1-25(2)5-4-10-6-11(13(34-3)7-12(10)39-25)22(33)38-24-21(32)19(30)17(28)15(37-24)9-35-23-20(31)18(29)16(27)14(8-26)36-23/h4-7,14-21,23-24,26-32H,8-9H2,1-3H3/t14-,15-,16-,17-,18+,19+,20-,21-,23-,24+/m1/s1

InChI Key

BKABLXWGRDWHDB-GWOWOUNZSA-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
Gentiana macrophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
Disaccharide
Glycosyl compound
O-glycosyl compound
O-methoxybenzoic acid or derivatives
Anisole
Alkyl aryl ether
Benzenoid
Oxane
Secondary alcohol
Carboxylic acid ester
Oxacycle
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Acetal
Organic oxide
Alcohol
Organooxygen compound
Primary alcohol
Organic oxygen compound
Hydrocarbon derivative
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	-0.56	ALOGPS
logP	-1.5	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	11.9	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	214.06 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	129.02 m³·mol⁻¹	ChemAxon
Polarizability	55.37 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

FDB000014

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

10745406

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate (NP0149502)

MOL for NP0149502 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate)

3D MOL for NP0149502 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate)

3D SDF for NP0149502 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate)

3D-SDF for NP0149502 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate)

PDB for NP0149502 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate)

3D PDB for NP0149502 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate)

SMILES for NP0149502 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate)

INCHI for NP0149502 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate)

Structure for NP0149502 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate)

3D Structure for NP0149502 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 7-methoxy-2,2-dimethylchromene-6-carboxylate)