NP-MRD: Showing NP-Card for (1r,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(2r,3r,4s,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde (NP0320058)

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Record Information

Version

2.0

Created at

2022-09-11 21:26:36 UTC

Updated at

2022-09-11 21:26:37 UTC

NP-MRD ID

NP0320058

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(1R,4aS,7S,7aS)-7-hydroxy-7-methyl-1-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R,3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carbaldehyde belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. (1r,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(2r,3r,4s,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde is found in Pedicularis plicata. Based on a literature review very few articles have been published on (1R,4aS,7S,7aS)-7-hydroxy-7-methyl-1-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R,3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carbaldehyde.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112223262D          

 36 39  0  0  1  0            999 V2000
    0.4243   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4743   -2.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -4.8229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2102   -5.2354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2102   -6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -4.8229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6391   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -3.9979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6391   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523   -6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -4.8229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9233   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  2  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  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  6  0  0  0
 17 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 15 34  1  0  0  0  0
 34 35  1  6  0  0  0
 12 36  1  0  0  0  0
 36  6  1  6  0  0  0
  2 36  1  0  0  0  0
M  END

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
    2.6318    3.2083   -3.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4987    2.0037   -3.3659 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2296    2.2300   -2.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4874    1.9240   -4.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1040    0.7224   -5.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2713   -0.1613   -4.4208 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2670   -0.8265   -5.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6816   -2.0283   -6.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8385   -2.6078   -6.7251 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0362   -0.3707   -5.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6987    0.7723   -4.6467 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2530    0.9069   -3.3436 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6712    0.0103   -2.4528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0379    0.6365   -1.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6152   -0.4172   -0.5507 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3296    0.1598    0.4681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7451   -0.8058    1.4186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4804   -0.1086    2.3495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0584   -0.1542    3.6349 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0063   -0.6179    4.6764 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6454   -1.8070    4.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2086   -0.7377    5.9856 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9979   -1.2294    7.0084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6861    0.6520    6.2782 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8820    0.6781    7.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3213    1.9146    7.7970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7863    0.9721    5.2437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5407    1.2199    4.0983 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7629    1.7614    3.0810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810   -1.7390    0.6859 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3130   -2.6554    1.4894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0268   -2.3864   -0.5186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9964   -3.1050   -1.1927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5508   -1.2668   -1.4197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8288   -1.7314   -2.5070 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322    0.7021   -3.3360 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9240    3.0561   -4.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1590    3.5789   -2.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151    4.0367   -3.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8182    1.7888   -1.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4983    2.8576   -5.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273    1.7804   -4.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9915    0.1904   -5.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5173    1.0813   -6.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9933   -0.9365   -4.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6641   -2.4335   -5.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3470   -0.9023   -6.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9996    1.9330   -3.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8818    1.2511   -1.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6325    1.3147   -0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1622   -1.1079   -0.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8859   -1.3462    1.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1379   -0.8024    3.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8007    0.1463    4.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0252   -2.5458    4.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3262   -1.3650    5.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0651   -2.2257    6.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4941    1.4009    6.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5349    0.4050    8.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0631   -0.0625    7.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9516    2.6690    7.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3972    1.8724    4.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2814    2.4742    2.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4920   -1.0767    0.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2556   -2.8178    1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1698   -3.0252   -0.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9934   -4.0518   -0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4220   -0.6494   -1.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2880   -2.4202   -3.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0160    0.2137   -2.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6 36  1  0
 36 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 28  1  0
 28 29  1  0
 28 27  1  0
 27 24  1  0
 24 25  1  0
 25 26  1  0
 24 22  1  0
 22 23  1  0
 22 20  1  0
 20 21  1  0
 17 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 12 11  1  0
 11 10  1  0
 10  7  2  0
  7  8  1  0
  8  9  2  0
 36  2  1  0
 34 15  1  0
  7  6  1  0
 20 19  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  1
 36 70  1  1
 12 48  1  1
 14 49  1  0
 14 50  1  0
 15 51  1  1
 17 52  1  1
 19 53  1  6
 28 62  1  1
 29 63  1  0
 24 58  1  1
 25 59  1  0
 25 60  1  0
 26 61  1  0
 22 56  1  6
 23 57  1  0
 20 54  1  1
 21 55  1  0
 30 64  1  6
 31 65  1  0
 32 66  1  1
 33 67  1  0
 34 68  1  6
 35 69  1  0
 10 47  1  0
  8 46  1  0
M  END


  Mrv1652309112223262D          

 36 39  0  0  1  0            999 V2000
    0.4243   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4743   -2.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -4.8229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2102   -5.2354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2102   -6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -4.8229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6391   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -3.9979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6391   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523   -6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -4.8229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9233   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  2  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  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  6  0  0  0
 17 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 15 34  1  0  0  0  0
 34 35  1  6  0  0  0
 12 36  1  0  0  0  0
 36  6  1  6  0  0  0
  2 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320058

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O14/c1-22(31)3-2-9-8(4-23)6-32-20(12(9)22)33-7-11-14(26)15(27)17(29)21(35-11)36-18-16(28)13(25)10(5-24)34-19(18)30/h4,6,9-21,24-31H,2-3,5,7H2,1H3/t9-,10-,11-,12-,13-,14-,15+,16+,17-,18-,19-,20+,21+,22+/m1/s1

> <INCHI_KEY>
WILPSDUESCCQEW-KZBZQOKASA-N

> <FORMULA>
C22H34O14

> <MOLECULAR_WEIGHT>
522.5

> <EXACT_MASS>
522.194855775

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
50.2248052049235

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-3.9691417586666664

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.156032421198523

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.267478090821312

> <JCHEM_PKA_STRONGEST_BASIC>
-2.969803499781979

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999997

> <JCHEM_REFRACTIVITY>
113.99900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       0.792  -3.319   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.752  -3.956   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.590   2.547   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.591  -7.463   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.925  -9.773   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.259  -9.003   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.592  -9.773   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.592 -11.313   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.926  -9.003   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.260  -9.773   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.926  -7.463   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.260  -6.693   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      15.593  -7.463   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      11.592  -6.693   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.259  -7.463   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.925  -6.693   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.258  -9.773   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.258 -11.313   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.924  -9.003   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.590  -9.773   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.924  -7.463   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.590  -6.693   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   36                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   36                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   36                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   34                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   19   29                                                  
CONECT   29   28                                                            
CONECT   30   17   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   15   35                                                  
CONECT   35   34                                                            
CONECT   36   12    6    2                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₄O₁₄

Average Mass

522.5000 Da

Monoisotopic Mass

522.19486 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@]1(O)CC[C@H]2[C@@H]1[C@H](OC[C@H]1O[C@@H](O[C@H]3[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]3O)[C@H](O)[C@@H](O)[C@@H]1O)OC=C2C=O

InChI Identifier

InChI=1S/C22H34O14/c1-22(31)3-2-9-8(4-23)6-32-20(12(9)22)33-7-11-14(26)15(27)17(29)21(35-11)36-18-16(28)13(25)10(5-24)34-19(18)30/h4,6,9-21,24-31H,2-3,5,7H2,1H3/t9-,10-,11-,12-,13-,14-,15+,16+,17-,18-,19-,20+,21+,22+/m1/s1

InChI Key

WILPSDUESCCQEW-KZBZQOKASA-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
Pedicularis plicata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Disaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Oxane
Cyclic alcohol
Vinylogous ester
Tertiary alcohol
Hemiacetal
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Primary alcohol
Aldehyde
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	-4	ChemAxon
pKa (Strongest Acidic)	11.27	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	114 m³·mol⁻¹	ChemAxon
Polarizability	50.22 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163038474

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(2r,3r,4s,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde (NP0320058)

MOL for NP0320058 ((1r,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(2r,3r,4s,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde)

3D MOL for NP0320058 ((1r,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(2r,3r,4s,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde)

3D SDF for NP0320058 ((1r,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(2r,3r,4s,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde)

3D-SDF for NP0320058 ((1r,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(2r,3r,4s,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde)

PDB for NP0320058 ((1r,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(2r,3r,4s,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde)

3D PDB for NP0320058 ((1r,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(2r,3r,4s,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde)

SMILES for NP0320058 ((1r,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(2r,3r,4s,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde)

INCHI for NP0320058 ((1r,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(2r,3r,4s,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde)

Structure for NP0320058 ((1r,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(2r,3r,4s,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde)

3D Structure for NP0320058 ((1r,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(2r,3r,4s,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbaldehyde)