NP-MRD: Showing NP-Card for (4ar,7r,7as)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-4-ylmethyl 3-methylbutanoate (NP0182133)

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Record Information

Version

2.0

Created at

2022-09-03 20:46:04 UTC

Updated at

2022-09-03 20:46:04 UTC

NP-MRD ID

NP0182133

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4ar,7r,7as)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-4-ylmethyl 3-methylbutanoate

Description

[(4AR,7R,7aS)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methylbutanoate 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. (4ar,7r,7as)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-4-ylmethyl 3-methylbutanoate is found in Centranthus macrosiphon, Centranthus ruber, Valeriana capensis, Valeriana edulis, Valeriana jatamansi, Valeriana microphylla, Valeriana officinalis, Valeriana sitchensis and Valerianella locusta. Based on a literature review very few articles have been published on [(4aR,7R,7aS)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032222462D          

 30 32  0  0  1  0            999 V2000
   -4.7610   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9360   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6985   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136   -1.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2136   -2.7299    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0420   -3.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8267   -3.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  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  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  8 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 19 27  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  6  0  0  0
  5 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  6  0  0  0
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
    2.7642    5.9353    0.7401 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6162    4.4530    0.7849 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600    3.7559    1.2858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4808    3.8242    0.2960 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    2.4525    0.3613 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2099    1.9369    1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2225    0.5138    0.7831 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9802   -0.2659    1.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0203    0.1148    2.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1078   -0.7524    2.1230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0218   -0.9955    1.1146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8957   -0.3957    0.0034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1644   -1.9340    1.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0002   -1.9386   -0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5132   -0.5368   -0.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1646   -2.8696    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0677   -1.3767    0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305   -1.6992   -0.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6809   -0.6791   -1.2722 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0746   -0.8078   -0.9507 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0285   -1.1103   -1.9073 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6240   -1.2815   -3.0907 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4715   -1.2424   -1.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8224   -2.4533   -0.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3361   -2.4407   -0.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2387   -2.3409    0.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2348    0.6424   -0.7562 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1439    1.7710   -0.9491 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8290    2.7075   -2.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9873    1.9177   -2.0177 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9644    6.3626    1.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6299    6.1689    0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8686    6.3462    0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2985    2.0257    0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7112    2.4818    0.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4835    1.9677    2.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1585    0.0367    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4672    1.1099    1.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5940    0.2947    3.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7845   -2.9506    1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8026   -1.5879    2.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3361   -2.2591   -0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6116   -0.5489   -0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1497   -0.1451   -1.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1639    0.1114    0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2597   -3.1373    1.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0897   -2.3287   -0.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0412   -3.8009   -0.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8860   -2.0781    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5098   -0.8084   -2.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0227   -1.3667   -2.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8593   -0.3160   -1.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5460   -3.3866   -1.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6222   -2.7313    0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7257   -1.4030   -0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8362   -3.1240   -1.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9193   -2.8950    1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2973   -1.2702    0.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2308   -2.7651    0.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7828    0.8735   -1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9188    3.7962   -1.9329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0356    2.4233   -2.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8 17  2  0
 17 18  1  0
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 27  7  1  0
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  2  1  1  0
  2  3  2  0
  5 28  1  0
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 29 30  1  0
  7  8  1  0
 28 30  1  6
 28 27  1  0
 15 43  1  0
 15 44  1  0
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 14 42  1  0
 16 46  1  0
 16 47  1  0
 16 48  1  0
 13 40  1  0
 13 41  1  0
  9 38  1  0
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 17 49  1  0
 19 50  1  6
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  6 36  1  0
  5 34  1  1
  1 31  1  0
  1 32  1  0
  1 33  1  0
 29 61  1  0
 29 62  1  0
M  END


  Mrv1652309032222462D          

 30 32  0  0  1  0            999 V2000
   -4.7610   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9360   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6985   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136   -1.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2136   -2.7299    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0420   -3.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8267   -3.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  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  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  8 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 19 27  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  6  0  0  0
  5 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0182133

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)OCC1=COC(OC(=O)CC(C)C)[C@H]2[C@H]1CC(OC(C)=O)[C@]21CO1

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O8/c1-12(2)6-18(24)26-9-15-10-27-21(30-19(25)7-13(3)4)20-16(15)8-17(29-14(5)23)22(20)11-28-22/h10,12-13,16-17,20-21H,6-9,11H2,1-5H3/t16-,17?,20+,21?,22+/m0/s1

> <INCHI_KEY>
PHHROXLDZHUIGO-KQUCSHIGSA-N

> <FORMULA>
C22H32O8

> <MOLECULAR_WEIGHT>
424.49

> <EXACT_MASS>
424.20971799

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.807010022487674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(4aR,7R,7aS)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methylbutanoate

> <JCHEM_LOGP>
2.4861954756666655

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.139397746784327

> <JCHEM_POLAR_SURFACE_AREA>
100.66

> <JCHEM_REFRACTIVITY>
104.55789999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,7R,7aS)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-4-ylmethyl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.887  -5.184   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.347  -5.184   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.577  -6.517   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -6.577  -3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -5.037  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.132  -2.604   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.132  -5.096   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.812  -6.602   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.276  -6.126   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    8   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   19    7   28                                                  
CONECT   28   27    5   29   30                                             
CONECT   29   28   30                                                       
CONECT   30   29   28                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
[(4AR,7R,7as)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methylbutanoic acid	Generator

Chemical Formula

C₂₂H₃₂O₈

Average Mass

424.4900 Da

Monoisotopic Mass

424.20972 Da

IUPAC Name

[(4aR,7R,7aS)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methylbutanoate

Traditional Name

(4aR,7R,7aS)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-4-ylmethyl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)OCC1=COC(OC(=O)CC(C)C)[C@H]2[C@H]1CC(OC(C)=O)[C@]21CO1

InChI Identifier

InChI=1S/C22H32O8/c1-12(2)6-18(24)26-9-15-10-27-21(30-19(25)7-13(3)4)20-16(15)8-17(29-14(5)23)22(20)11-28-22/h10,12-13,16-17,20-21H,6-9,11H2,1-5H3/t16-,17?,20+,21?,22+/m0/s1

InChI Key

PHHROXLDZHUIGO-KQUCSHIGSA-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
Centranthus macrosiphon	LOTUS Database	35616633
Centranthus ruber	LOTUS Database	35616633
Valeriana capensis	LOTUS Database	35616633
Valeriana edulis	LOTUS Database	35616633
Valeriana jatamansi	LOTUS Database	35616633
Valeriana microphylla	LOTUS Database	35616633
Valeriana officinalis	LOTUS Database	35616633
Valeriana sitchensis	LOTUS Database	35616633
Valerianella locusta	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

Iridoid-skeleton
Bicyclic monoterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.49	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	100.66 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	104.56 m³·mol⁻¹	ChemAxon
Polarizability	44.81 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

137796089

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4ar,7r,7as)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-4-ylmethyl 3-methylbutanoate (NP0182133)

MOL for NP0182133 ((4ar,7r,7as)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-4-ylmethyl 3-methylbutanoate)

3D MOL for NP0182133 ((4ar,7r,7as)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-4-ylmethyl 3-methylbutanoate)

3D SDF for NP0182133 ((4ar,7r,7as)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-4-ylmethyl 3-methylbutanoate)

3D-SDF for NP0182133 ((4ar,7r,7as)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-4-ylmethyl 3-methylbutanoate)

PDB for NP0182133 ((4ar,7r,7as)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-4-ylmethyl 3-methylbutanoate)

3D PDB for NP0182133 ((4ar,7r,7as)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-4-ylmethyl 3-methylbutanoate)

SMILES for NP0182133 ((4ar,7r,7as)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-4-ylmethyl 3-methylbutanoate)

INCHI for NP0182133 ((4ar,7r,7as)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-4-ylmethyl 3-methylbutanoate)

Structure for NP0182133 ((4ar,7r,7as)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-4-ylmethyl 3-methylbutanoate)

3D Structure for NP0182133 ((4ar,7r,7as)-6-(acetyloxy)-1-[(3-methylbutanoyl)oxy]-4a,5,6,7a-tetrahydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-4-ylmethyl 3-methylbutanoate)