NP-MRD: Showing NP-Card for methyl (1s,4as,5r,7as)-5-butoxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0323967)

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Record Information

Version

2.0

Created at

2022-09-12 03:43:56 UTC

Updated at

2022-09-12 03:43:56 UTC

NP-MRD ID

NP0323967

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,4as,5r,7as)-5-butoxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate

Description

Methyl (1S,4aS,5R,7aS)-5-butoxy-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate 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. methyl (1s,4as,5r,7as)-5-butoxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate is found in Gardenia jasminoides. Based on a literature review very few articles have been published on methyl (1S,4aS,5R,7aS)-5-butoxy-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122205432D          

 32 34  0  0  1  0            999 V2000
    2.7791   -0.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4935   -0.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2080   -0.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9225   -0.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6370   -0.8221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3514   -0.4096    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4377    0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2446    0.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5802    1.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4007    1.4223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6571   -0.1320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4641   -0.3036    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0161    0.3095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8231    0.1380    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3751    0.7511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1821    0.5796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7341    1.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4792    1.9773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4371   -0.2051    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2440   -0.3766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8850   -0.8181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1400   -1.6028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0780   -0.6466    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5260   -1.2597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7190   -1.0882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1670   -1.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3600   -1.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8080   -2.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010   -1.9713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0629   -2.9275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5109   -3.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1051   -0.7451    0.0000 C   0  0  1  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
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11  8  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 27  1  1  0  0  0
  6 32  1  0  0  0  0
 11 32  1  0  0  0  0
M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
    6.4712   -1.2853    2.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5846   -2.0204    1.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -1.1658    1.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3777   -1.8048    0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2186   -1.1155    0.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4791    0.1308   -0.0328 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7832    1.1235    0.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4621    1.1048    0.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6066    1.9163    1.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0071    2.7262    2.1886 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2257    0.1150   -0.5062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9376    0.4034   -1.3810 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6141   -0.7967   -1.5927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9071   -0.7732   -1.1239 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1125   -1.7163   -0.0937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3149   -1.4432    0.5264 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4740   -2.1180    1.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4505   -1.6834    2.6833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4505   -1.7484   -0.4285 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6903   -1.6514    0.1773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2928   -0.7330   -1.5635 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3189   -0.7890   -2.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9373   -1.0834   -2.1882 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7236   -0.4088   -3.3624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5442    1.0011   -2.6063 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4880    1.9194   -2.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5934    1.5676   -1.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6775    2.5178   -1.8520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7780    2.3370   -1.2571 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5606    3.7527   -2.5038 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6249    4.6734   -2.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5737    0.2427   -1.2603 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4139   -1.8395    2.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9535   -1.1897    3.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6425   -0.2605    2.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1170   -2.0704    0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3084   -3.0171    2.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6599   -0.1805    1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8680   -1.0748    2.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8980   -1.9917   -0.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1341   -2.8280    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5169    0.3408   -0.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2025    1.7617    1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0683    2.5748    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4202    1.3078    1.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1227    2.3189    3.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1958   -0.8824   -0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6072    1.1244   -0.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1662    0.2217   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3476   -0.3371    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5078   -3.2091    1.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4247   -1.7395    2.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6101   -0.7471    2.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2589   -2.7567   -0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2908   -1.1887   -0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1650    0.2492   -1.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5991   -1.7367   -2.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9321   -2.1941   -2.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1162   -0.9627   -3.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4610    2.8955   -3.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4930    4.3433   -3.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486    5.6449   -2.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9599    4.8095   -1.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7183   -0.5812   -1.9574 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 32  1  0
 32 27  1  0
 27 26  2  0
 26 25  1  0
 25 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
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 32  6  1  0
 23 14  1  0
 12 11  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  6 42  1  6
  7 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 11 47  1  1
 32 64  1  6
 26 60  1  0
 12 48  1  1
 14 49  1  1
 16 50  1  1
 17 51  1  0
 17 52  1  0
 18 53  1  0
 19 54  1  6
 20 55  1  0
 21 56  1  1
 22 57  1  0
 23 58  1  6
 24 59  1  0
 31 61  1  0
 31 62  1  0
 31 63  1  0
M  END


  Mrv1652309122205432D          

 32 34  0  0  1  0            999 V2000
    2.7791   -0.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4935   -0.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2080   -0.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9225   -0.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6370   -0.8221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3514   -0.4096    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4377    0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2446    0.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5802    1.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4007    1.4223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6571   -0.1320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4641   -0.3036    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0161    0.3095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8231    0.1380    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3751    0.7511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1821    0.5796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7341    1.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4792    1.9773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4371   -0.2051    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2440   -0.3766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8850   -0.8181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1400   -1.6028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0780   -0.6466    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5260   -1.2597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7190   -1.0882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1670   -1.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3600   -1.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8080   -2.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010   -1.9713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0629   -2.9275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5109   -3.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1051   -0.7451    0.0000 C   0  0  1  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
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11  8  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 27  1  1  0  0  0
  6 32  1  0  0  0  0
 11 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0323967

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCO[C@@H]1C=C(CO)[C@@H]2[C@H]1C(=CO[C@H]2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O11/c1-3-4-5-29-12-6-10(7-22)14-15(12)11(19(27)28-2)9-30-20(14)32-21-18(26)17(25)16(24)13(8-23)31-21/h6,9,12-18,20-26H,3-5,7-8H2,1-2H3/t12-,13-,14-,15+,16-,17+,18-,20+,21+/m1/s1

> <INCHI_KEY>
RYWUDXJHHMSWPB-SIWNXJGJSA-N

> <FORMULA>
C21H32O11

> <MOLECULAR_WEIGHT>
460.476

> <EXACT_MASS>
460.19446185

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.42060966362821

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,4aS,5R,7aS)-5-butoxy-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_LOGP>
-1.4005631239999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.194189465769028

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.206498879296978

> <JCHEM_PKA_STRONGEST_BASIC>
-2.741508424503115

> <JCHEM_POLAR_SURFACE_AREA>
164.36999999999998

> <JCHEM_REFRACTIVITY>
108.56990000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,4aS,5R,7aS)-5-butoxy-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       5.188  -1.535   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.521  -0.765   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.855  -1.535   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.189  -0.765   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.522  -1.535   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      11.856  -0.765   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.017   0.767   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.523   1.087   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.150   2.494   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      15.681   2.655   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      14.293  -0.246   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.800  -0.567   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      16.830   0.578   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      18.336   0.258   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      19.367   1.402   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      20.873   1.082   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.904   2.226   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      21.428   3.691   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      21.349  -0.383   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      22.856  -0.703   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      20.319  -1.527   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      20.795  -2.992   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      18.812  -1.207   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      17.782  -2.351   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      16.276  -2.031   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      15.245  -3.176   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.739  -2.856   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.708  -4.000   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.202  -3.680   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      13.184  -5.465   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.154  -6.609   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.263  -1.391   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   32                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23                                                            
CONECT   25   12   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   27    6   11                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,4as,5R,7as)-5-butoxy-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,7ah-cyclopenta[c]pyran-4-carboxylic acid	Generator

Chemical Formula

C₂₁H₃₂O₁₁

Average Mass

460.4760 Da

Monoisotopic Mass

460.19446 Da

IUPAC Name

methyl (1S,4aS,5R,7aS)-5-butoxy-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

Traditional Name

methyl (1S,4aS,5R,7aS)-5-butoxy-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

CAS Registry Number

Not Available

SMILES

CCCCO[C@@H]1C=C(CO)[C@@H]2[C@H]1C(=CO[C@H]2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)OC

InChI Identifier

InChI=1S/C21H32O11/c1-3-4-5-29-12-6-10(7-22)14-15(12)11(19(27)28-2)9-30-20(14)32-21-18(26)17(25)16(24)13(8-23)31-21/h6,9,12-18,20-26H,3-5,7-8H2,1-2H3/t12-,13-,14-,15+,16-,17+,18-,20+,21+/m1/s1

InChI Key

RYWUDXJHHMSWPB-SIWNXJGJSA-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
Gardenia jasminoides	LOTUS Database	35616633

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
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Dialkyl ether
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organooxygen compound
Primary 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	-1.4	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.37 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	108.57 m³·mol⁻¹	ChemAxon
Polarizability	47.42 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

102507166

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1s,4as,5r,7as)-5-butoxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0323967)

MOL for NP0323967 (methyl (1s,4as,5r,7as)-5-butoxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D MOL for NP0323967 (methyl (1s,4as,5r,7as)-5-butoxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D SDF for NP0323967 (methyl (1s,4as,5r,7as)-5-butoxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D-SDF for NP0323967 (methyl (1s,4as,5r,7as)-5-butoxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate)

PDB for NP0323967 (methyl (1s,4as,5r,7as)-5-butoxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D PDB for NP0323967 (methyl (1s,4as,5r,7as)-5-butoxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate)

SMILES for NP0323967 (methyl (1s,4as,5r,7as)-5-butoxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate)

INCHI for NP0323967 (methyl (1s,4as,5r,7as)-5-butoxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate)

Structure for NP0323967 (methyl (1s,4as,5r,7as)-5-butoxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D Structure for NP0323967 (methyl (1s,4as,5r,7as)-5-butoxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-4-carboxylate)