NP-MRD: Showing NP-Card for 5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-hexahydrospiro[naphthalene-1,3'-oxolan]-5-ylacetic acid (NP0269215)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 14:35:59 UTC

Updated at

2022-09-08 14:35:59 UTC

NP-MRD ID

NP0269215

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-hexahydrospiro[naphthalene-1,3'-oxolan]-5-ylacetic acid

Description

2-[5'-(Furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-octahydro-2H-spiro[naphthalene-1,3'-oxolane]-5-yl]acetic acid belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. 2-[5'-(Furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-octahydro-2H-spiro[naphthalene-1,3'-oxolane]-5-yl]acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251507282D          

 40 43  0  0  0  0            999 V2000
   -2.1027    1.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3133    1.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1263    0.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7286    0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3369    0.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2655    1.0218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1498   -0.3455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419   -0.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313   -0.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2183   -1.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6170   -0.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1908    0.3639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0077   -1.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9057   -0.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6528   -0.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2165   -0.7382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8178   -1.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3816   -2.0628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8087    0.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5558    1.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4537    1.8429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6436    1.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450    1.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1948   -2.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9841   -2.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1712   -3.1514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5924   -2.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8030   -2.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2007   -2.9958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160   -1.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0136   -2.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2341   -2.4623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8266   -1.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5594   -2.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501   -2.3282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0301   -1.6037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5543   -1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3508   -1.2364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990   -0.1976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 20 24  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  1  0  0  0  0
  8 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END

     RDKit          3D

 80 83  0  0  0  0  0  0  0  0999 V2000
    7.1077    2.6555    0.9299 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3280    1.6461    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386    1.5367    0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3439    2.4292    1.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2948    0.5337   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9119   -0.2068   -1.2197 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9513    0.4203   -0.2562 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1490   -0.5335   -0.9386 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3120    0.2349   -1.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0194    0.6784   -1.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8081   -0.4881   -0.7928 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9859   -1.3689   -1.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6234   -2.5368   -1.9418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2044   -0.0589   -0.3832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3187    1.4522   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6102    1.9428   -0.6944 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3868    2.8475    0.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6301    4.2095    0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3826    4.6361    1.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5933    3.6000    1.9182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0175    2.5133    1.4047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2397    0.7600   -0.9354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1452    0.0627   -1.5550 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7979    1.0390   -2.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8892   -0.8065    0.6785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2179   -1.4657    0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2795   -2.4177   -0.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0744   -1.6716    1.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7715   -2.1725    1.0451 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0353   -3.3459    0.3918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0010   -1.0846    0.3344 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0385   -0.0818    1.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564   -0.4601    2.6247 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256   -1.4300    0.0332 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3175   -1.4035    1.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6247   -1.8616    0.9685 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111   -2.8176   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9860   -3.3379   -0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5357   -4.1284    0.2073 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8648   -3.0766   -1.6902 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6433    2.8796    1.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1142    2.1944    1.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2126    3.5399    0.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8257    0.9842   -0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6761    2.2603    2.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6303    3.4747    1.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2480    2.3915    1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9751   -1.0846   -1.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2816   -0.2115   -2.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182    1.1875   -2.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5228    1.1587   -2.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423    1.4832   -0.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1024   -1.4891   -2.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6270   -0.8227   -2.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3559   -2.7561   -2.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5511    2.0765   -0.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769    1.5743    1.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4093    2.5648   -1.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2960    4.8276   -0.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7183    5.6651    1.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0491    1.5192    1.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6184   -0.7951   -1.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5949    1.1715   -3.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2764   -0.0167    1.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0988   -0.7886    0.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3964   -2.0691    1.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1523   -2.4580   -0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0133   -1.3506    2.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7015   -2.6179    1.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1704   -2.5126    1.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3453   -3.9984    1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2510    0.9558    1.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9828    0.0585    1.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1915   -0.7272    3.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0158   -2.0929    2.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5718   -0.4519    1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0980   -1.8820    1.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0464   -3.5528    0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2138   -2.9585   -1.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9380   -3.7740   -2.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  6
 12 13  1  0
 11 14  1  0
 14 15  1  1
 15 16  1  0
 16 22  1  0
 22 23  1  0
 23 24  1  0
 16 17  1  0
 17 21  2  0
 21 20  1  0
 20 19  1  0
 19 18  2  0
 14 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  1
 32 33  1  0
 31 34  1  0
 34 35  1  1
 35 36  1  0
 34 37  1  0
 37 38  1  0
 38 40  1  0
 38 39  2  0
 34  8  1  0
 31 11  1  0
 23 14  1  0
 18 17  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  2 44  1  0
  4 45  1  0
  4 46  1  0
  4 47  1  0
  8 48  1  6
  9 49  1  0
  9 50  1  0
 10 51  1  0
 10 52  1  0
 12 53  1  0
 12 54  1  0
 13 55  1  0
 15 56  1  0
 15 57  1  0
 16 58  1  6
 23 62  1  6
 24 63  1  0
 21 61  1  0
 19 60  1  0
 18 59  1  0
 25 64  1  1
 26 65  1  0
 26 66  1  0
 27 67  1  0
 28 68  1  0
 28 69  1  0
 29 70  1  1
 30 71  1  0
 32 72  1  0
 32 73  1  0
 33 74  1  0
 35 75  1  0
 35 76  1  0
 36 77  1  0
 37 78  1  0
 37 79  1  0
 40 80  1  0
M  END


  Mrv1533004251507282D          

 40 43  0  0  0  0            999 V2000
   -2.1027    1.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3133    1.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1263    0.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7286    0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3369    0.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2655    1.0218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1498   -0.3455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419   -0.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313   -0.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2183   -1.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6170   -0.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1908    0.3639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0077   -1.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9057   -0.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6528   -0.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2165   -0.7382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8178   -1.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3816   -2.0628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8087    0.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5558    1.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4537    1.8429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6436    1.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450    1.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1948   -2.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9841   -2.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1712   -3.1514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5924   -2.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8030   -2.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2007   -2.9958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160   -1.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0136   -2.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2341   -2.4623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8266   -1.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5594   -2.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501   -2.3282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0301   -1.6037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5543   -1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3508   -1.2364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990   -0.1976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 20 24  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  1  0  0  0  0
  8 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0269215

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC1CCC2(CO)C3(CC(OC3O)C3=COC=C3)C(CO)CC(O)C2(CO)C1(CO)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O12/c1-3-16(2)23(36)40-21-4-6-26(14-31)27(9-19(39-24(27)37)17-5-7-38-12-17)18(11-29)8-20(33)28(26,15-32)25(21,13-30)10-22(34)35/h3,5,7,12,18-21,24,29-33,37H,4,6,8-11,13-15H2,1-2H3,(H,34,35)

> <INCHI_KEY>
CPJNTZBFGMGXON-UHFFFAOYSA-N

> <FORMULA>
C28H40O12

> <MOLECULAR_WEIGHT>
568.616

> <EXACT_MASS>
568.251976728

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.542978945931395

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-octahydro-2H-spiro[naphthalene-1,3'-oxolane]-5-yl]acetic acid

> <ALOGPS_LOGP>
-0.53

> <JCHEM_LOGP>
-1.148204747000002

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.90440897750674

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.04292321657932

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6066561070473266

> <JCHEM_POLAR_SURFACE_AREA>
207.34999999999997

> <JCHEM_REFRACTIVITY>
138.57260000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-hexahydrospiro[naphthalene-1,3'-oxolane]-5-ylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -3.925   3.250   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.452   2.803   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.102   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.227   0.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.629   0.855   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.496   1.907   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.280  -0.645   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.194  -1.092   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.318  -0.040   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.792  -0.488   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.141  -1.988   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.885  -0.639   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.089   0.679   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.614  -2.435   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.424  -0.907   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.818  -0.254   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.871  -1.378   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.127  -2.726   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.179  -3.851   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.110   1.259   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.504   1.912   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.314   3.440   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.801   3.731   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.057   2.383   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.964  -3.935   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.437  -4.383   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.786  -5.883   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.839  -4.987   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.366  -4.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.241  -5.592   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.017  -3.040   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.892  -4.092   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.437  -4.596   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.543  -2.592   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.044  -4.049   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.467  -4.346   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.056  -2.994   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.035  -1.907   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -2.522  -2.308   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -1.118  -0.369   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   34                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14   31                                             
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   18   25                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18                                                            
CONECT   20   16   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   20                                                       
CONECT   25   14   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   11   32   34                                             
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31    8   35   37                                             
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
2-[5'-(Furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-octahydro-2H-spiro[naphthalene-1,3'-oxolane]-5-yl]acetate	Generator

Chemical Formula

C₂₈H₄₀O₁₂

Average Mass

568.6160 Da

Monoisotopic Mass

568.25198 Da

IUPAC Name

2-[5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-octahydro-2H-spiro[naphthalene-1,3'-oxolane]-5-yl]acetic acid

Traditional Name

5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-hexahydrospiro[naphthalene-1,3'-oxolane]-5-ylacetic acid

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1CCC2(CO)C3(CC(OC3O)C3=COC=C3)C(CO)CC(O)C2(CO)C1(CO)CC(O)=O

InChI Identifier

InChI=1S/C28H40O12/c1-3-16(2)23(36)40-21-4-6-26(14-31)27(9-19(39-24(27)37)17-5-7-38-12-17)18(11-29)8-20(33)28(26,15-32)25(21,13-30)10-22(34)35/h3,5,7,12,18-21,24,29-33,37H,4,6,8-11,13-15H2,1-2H3,(H,34,35)

InChI Key

CPJNTZBFGMGXON-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Heteroaromatic compound
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Hemiacetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Primary alcohol
Organooxygen compound
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	-0.53	ALOGPS
logP	-1.1	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	4.04	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	207.35 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	138.57 m³·mol⁻¹	ChemAxon
Polarizability	57.54 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-hexahydrospiro[naphthalene-1,3'-oxolan]-5-ylacetic acid (NP0269215)

MOL for NP0269215 (5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-hexahydrospiro[naphthalene-1,3'-oxolan]-5-ylacetic acid)

3D MOL for NP0269215 (5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-hexahydrospiro[naphthalene-1,3'-oxolan]-5-ylacetic acid)

3D SDF for NP0269215 (5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-hexahydrospiro[naphthalene-1,3'-oxolan]-5-ylacetic acid)

3D-SDF for NP0269215 (5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-hexahydrospiro[naphthalene-1,3'-oxolan]-5-ylacetic acid)

PDB for NP0269215 (5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-hexahydrospiro[naphthalene-1,3'-oxolan]-5-ylacetic acid)

3D PDB for NP0269215 (5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-hexahydrospiro[naphthalene-1,3'-oxolan]-5-ylacetic acid)

SMILES for NP0269215 (5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-hexahydrospiro[naphthalene-1,3'-oxolan]-5-ylacetic acid)

INCHI for NP0269215 (5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-hexahydrospiro[naphthalene-1,3'-oxolan]-5-ylacetic acid)

Structure for NP0269215 (5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-hexahydrospiro[naphthalene-1,3'-oxolan]-5-ylacetic acid)

3D Structure for NP0269215 (5'-(furan-3-yl)-2',4-dihydroxy-2,4a,5,8a-tetrakis(hydroxymethyl)-6-[(2-methylbut-2-enoyl)oxy]-hexahydrospiro[naphthalene-1,3'-oxolan]-5-ylacetic acid)