NP-MRD: Showing NP-Card for (2z,4e)-5-[(1s,3r,5r,8r)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid (NP0320599)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 22:20:23 UTC

Updated at

2022-09-11 22:20:23 UTC

NP-MRD ID

NP0320599

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z,4e)-5-[(1s,3r,5r,8r)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid

Description

(2Z,4E)-5-[(1S,3R,5R,8R)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]Octan-8-yl]-3-methylpenta-2,4-dienoic acid belongs to the class of organic compounds known as abscisic acids and derivatives. These are terpene compounds containing the abscisic acid moiety, which is characterized by a 3-methylpenta-2,4-dienoic acid attached to the C1 carbon of a 4-oxocyclohex-2-ene moiety. (2z,4e)-5-[(1s,3r,5r,8r)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid is found in Prunus domestica. Based on a literature review very few articles have been published on (2Z,4E)-5-[(1S,3R,5R,8R)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]Octan-8-yl]-3-methylpenta-2,4-dienoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122200202D          

 32 34  0  0  1  0            999 V2000
    2.7872    2.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1115    2.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1835    3.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5078    3.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    4.7068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601    3.5364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638    2.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786    1.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6075    0.8158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1600    0.0002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393   -0.1110    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5651   -0.9696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6436    0.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015    0.8158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8708    0.8310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2390    0.1014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0627    0.0550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4344   -0.6815    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2581   -0.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7101   -0.0376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -1.3716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3542   -2.1082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1588   -1.3253    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7068   -2.0155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7870   -0.5888    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9633   -0.5425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6436    1.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393    1.7427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2733    2.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1942    1.2283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1942    0.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6339    0.1420    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 14 27  1  0  0  0  0
 27 28  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
   -6.1101    0.3693    1.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7050    0.2278    0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6384    0.1760   -0.5615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4323    0.0415   -1.9847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4659    0.0052   -2.7446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2180   -0.0537   -2.6232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3123    0.1579    0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3959    0.2163    0.9799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9833    0.1480    0.6887 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3294   -0.3158    1.8370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5714   -0.6559   -0.5071 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3800   -1.8633   -0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1290   -1.0513   -0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7103    0.1063    0.2458 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9199   -0.0222   -0.3899 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0068   -0.2650    0.4321 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8493    0.7963    0.2420 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1518    0.6597    0.5010 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9195    1.6518   -0.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2866    1.5681   -0.1732 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7702   -0.6723    0.3215 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7090   -1.3637    1.5306 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9130   -1.4434   -0.6821 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7154   -0.6767   -1.8344 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5665   -1.5959    0.0284 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8396   -2.4015    1.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0754    1.4448    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3968    1.5055    0.2681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8854    2.6229    1.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9533    1.5676   -1.0587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039    0.3509   -1.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715    0.1877   -2.8474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6078   -0.4811    2.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7865    1.3430    2.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1871    0.2108    1.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6990    0.2381   -0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0406   -0.7056   -3.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9278    0.0581   -0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7586    0.3190    2.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4243   -1.2928    1.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7317   -2.7881   -0.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2098   -2.0443   -0.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7328   -1.8252   -1.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2426   -1.4452   -1.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053   -1.8494    0.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9329   -0.0299    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7485   -0.3228    1.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3780    1.0033    1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7531    1.3983   -1.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5385    2.6811   -0.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7210    1.9581   -0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8177   -0.5682   -0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8983   -0.7753    2.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3056   -2.4401   -0.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7446   -1.2150   -2.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9242   -2.1902   -0.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8383   -3.3460    0.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5318    2.1342    0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3931    1.8852   -0.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1900    2.2171    2.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083    3.4113    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8104    3.0391    0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  1
  9 28  1  0
 28 29  1  1
 28 27  1  0
 27 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  1  6
 11 31  1  0
 31 32  2  0
 31 30  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
  2  3  2  0
  3  4  1  0
  4  6  1  0
  4  5  2  0
 11  9  1  0
 25 16  1  0
 30 28  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  7 38  1  0
  8 39  1  0
 10 40  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
 27 58  1  0
 27 59  1  0
 14 46  1  1
 13 44  1  0
 13 45  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
 16 47  1  1
 18 48  1  1
 19 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  6
 22 53  1  0
 23 54  1  6
 24 55  1  0
 25 56  1  6
 26 57  1  0
  3 36  1  0
  6 37  1  0
M  END


  Mrv1652309122200202D          

 32 34  0  0  1  0            999 V2000
    2.7872    2.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1115    2.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1835    3.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5078    3.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    4.7068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601    3.5364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638    2.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786    1.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6075    0.8158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1600    0.0002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393   -0.1110    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5651   -0.9696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6436    0.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015    0.8158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8708    0.8310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2390    0.1014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0627    0.0550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4344   -0.6815    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2581   -0.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7101   -0.0376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -1.3716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3542   -2.1082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1588   -1.3253    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7068   -2.0155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7870   -0.5888    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9633   -0.5425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6436    1.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393    1.7427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2733    2.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1942    1.2283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1942    0.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6339    0.1420    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 14 27  1  0  0  0  0
 27 28  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0320599

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\[C@]1(O)[C@@]2(C)C[C@@H](C[C@]1(C)C(=O)O2)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O11/c1-10(6-13(23)24)4-5-21(29)19(2)7-11(8-20(21,3)32-18(19)28)30-17-16(27)15(26)14(25)12(9-22)31-17/h4-6,11-12,14-17,22,25-27,29H,7-9H2,1-3H3,(H,23,24)/b5-4+,10-6-/t11-,12-,14-,15+,16-,17-,19-,20-,21-/m1/s1

> <INCHI_KEY>
BJDUPNIPMKDXBF-GJNCRGBLSA-N

> <FORMULA>
C21H30O11

> <MOLECULAR_WEIGHT>
458.46

> <EXACT_MASS>
458.178811786

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
45.06078491482232

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,4E)-5-[(1S,3R,5R,8R)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid

> <JCHEM_LOGP>
-1.2931103963333324

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.084237727101991

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.356051248038216

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835415774077

> <JCHEM_POLAR_SURFACE_AREA>
183.20999999999998

> <JCHEM_REFRACTIVITY>
107.3776

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4E)-5-[(1S,3R,5R,8R)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid

> <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       5.203   3.951   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.941   4.834   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.076   6.368   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.815   7.252   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.949   8.786   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.419   6.601   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.546   4.184   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.387   2.370   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.134   1.523   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.165   0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.567  -0.207   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.055  -1.810   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.068   0.135   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.736   1.523   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.359   1.551   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.046   0.189   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.584   0.103   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.278  -1.272   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.815  -1.359   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.659  -0.070   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.434  -2.560   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.128  -3.935   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.896  -2.474   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.053  -3.762   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.202  -1.099   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.665  -1.013   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.068   2.910   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.567   3.253   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.510   4.559   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.363   2.293   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.363   0.753   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.183   0.265   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   28                                             
CONECT   10    9                                                            
CONECT   11    9   12   13   31                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
CONECT   27   14   28                                                       
CONECT   28   27    9   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   11   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
(2Z,4E)-5-[(1S,3R,5R,8R)-8-Hydroxy-1,5-dimethyl-7-oxo-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoate	Generator

Chemical Formula

C₂₁H₃₀O₁₁

Average Mass

458.4600 Da

Monoisotopic Mass

458.17881 Da

IUPAC Name

(2Z,4E)-5-[(1S,3R,5R,8R)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid

Traditional Name

(2Z,4E)-5-[(1S,3R,5R,8R)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid

CAS Registry Number

Not Available

SMILES

C\C(\C=C\[C@]1(O)[C@@]2(C)C[C@@H](C[C@]1(C)C(=O)O2)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=C\C(O)=O

InChI Identifier

InChI=1S/C21H30O11/c1-10(6-13(23)24)4-5-21(29)19(2)7-11(8-20(21,3)32-18(19)28)30-17-16(27)15(26)14(25)12(9-22)31-17/h4-6,11-12,14-17,22,25-27,29H,7-9H2,1-3H3,(H,23,24)/b5-4+,10-6-/t11-,12-,14-,15+,16-,17-,19-,20-,21-/m1/s1

InChI Key

BJDUPNIPMKDXBF-GJNCRGBLSA-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
Prunus domestica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as abscisic acids and derivatives. These are terpene compounds containing the abscisic acid moiety, which is characterized by a 3-methylpenta-2,4-dienoic acid attached to the C1 carbon of a 4-oxocyclohex-2-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Abscisic acids and derivatives

Alternative Parents

Substituents

Abscisic acid
Saccharolipid
Terpene glycoside
Terpene lactone
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Caprolactone
Medium-chain fatty acid
Branched fatty acid
Oxepane
Hydroxy fatty acid
Methyl-branched fatty acid
Heterocyclic fatty acid
Unsaturated fatty acid
Gamma butyrolactone
Fatty acid
Monosaccharide
Fatty acyl
Oxane
Dicarboxylic acid or derivatives
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Lactone
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Acetal
Organooxygen compound
Carbonyl group
Alcohol
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	-1.3	ChemAxon
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	107.38 m³·mol⁻¹	ChemAxon
Polarizability	45.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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

162987645

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z,4e)-5-[(1s,3r,5r,8r)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid (NP0320599)

MOL for NP0320599 ((2z,4e)-5-[(1s,3r,5r,8r)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

3D MOL for NP0320599 ((2z,4e)-5-[(1s,3r,5r,8r)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

3D SDF for NP0320599 ((2z,4e)-5-[(1s,3r,5r,8r)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

3D-SDF for NP0320599 ((2z,4e)-5-[(1s,3r,5r,8r)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

PDB for NP0320599 ((2z,4e)-5-[(1s,3r,5r,8r)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

3D PDB for NP0320599 ((2z,4e)-5-[(1s,3r,5r,8r)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

SMILES for NP0320599 ((2z,4e)-5-[(1s,3r,5r,8r)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

INCHI for NP0320599 ((2z,4e)-5-[(1s,3r,5r,8r)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

Structure for NP0320599 ((2z,4e)-5-[(1s,3r,5r,8r)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

3D Structure for NP0320599 ((2z,4e)-5-[(1s,3r,5r,8r)-8-hydroxy-1,5-dimethyl-7-oxo-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)