NP-MRD: Showing NP-Card for (2r,3s,4r,6s)-3-(acetyloxy)-6-[(2e)-3-[(2r)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(1e)-2-phenylethenyl]oxan-4-yl acetate (NP0304781)

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Record Information

Version

2.0

Created at

2022-09-10 20:07:03 UTC

Updated at

2022-09-10 20:07:03 UTC

NP-MRD ID

NP0304781

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4r,6s)-3-(acetyloxy)-6-[(2e)-3-[(2r)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(1e)-2-phenylethenyl]oxan-4-yl acetate

Description

(2R,3S,4R,6S)-3-(acetyloxy)-6-[(2E)-3-[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]prop-2-en-1-yl]-2-[(E)-2-phenylethenyl]oxan-4-yl acetate belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond. (2r,3s,4r,6s)-3-(acetyloxy)-6-[(2e)-3-[(2r)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(1e)-2-phenylethenyl]oxan-4-yl acetate is found in Cryptocarya moschata. Based on a literature review very few articles have been published on (2R,3S,4R,6S)-3-(acetyloxy)-6-[(2E)-3-[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]prop-2-en-1-yl]-2-[(E)-2-phenylethenyl]oxan-4-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102222072D          

 32 34  0  0  1  0            999 V2000
    2.1434   -0.4125    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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   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
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -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 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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 20 26  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
   -4.3673   -3.3514   -0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0791   -2.7052    0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4546   -2.9502    1.3665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4914   -1.7692   -0.5169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904   -1.1365   -0.2244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5233    0.3577   -0.1376 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7710    0.6901    0.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4616    1.7933    0.3829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6956    2.1510    1.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2802    1.3497    2.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4569    1.8089    2.6044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0326    3.0103    2.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4411    3.7981    1.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2827    3.3563    0.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4391    1.0212    0.3817 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7604    0.7794   -0.1834 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8458    1.1514    0.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1867    1.1905    0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1944    0.4078    0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5219    0.4801   -0.1640 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1408    1.8176    0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6000    1.8705   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3341    0.7933    0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7179   -0.4980    0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4358   -1.5361    0.4238 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3325   -0.5703    0.3822 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9973   -0.5419   -0.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2084   -1.2953   -1.2425 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1468   -2.6451   -1.4573 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0441   -3.2510   -2.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4153   -4.6728   -2.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3822   -2.6043   -3.6729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3937   -4.3785    0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5414   -3.3745   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1926   -2.7835    0.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9371   -1.5278    0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545    0.7121   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1407   -0.0137    1.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0446    2.4680   -0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8437    0.4206    2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9498    1.1990    3.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9465    3.3723    2.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8653    4.7496    1.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8243    4.0064   -0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8977    1.5517   -1.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673    2.1806    1.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205    0.4186    1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3383    1.8830   -0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -0.2735    1.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3732    0.2273   -1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7945    2.2722    1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7503    2.5220   -0.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0751    2.8430   -0.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4245    0.8563    0.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214   -1.1878   -0.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7220   -0.4879   -1.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5735   -0.8083   -2.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3811   -4.7620   -3.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3837   -5.2802   -1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3668   -5.1050   -3.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 32  2  0
 30 29  1  0
 29 28  1  0
 28 27  1  0
 27 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
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 22 23  2  0
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 24 26  1  0
 16 15  1  0
 15  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 28  1  0
 26 20  1  0
 14  9  1  0
 31 58  1  0
 31 59  1  0
 31 60  1  0
 28 57  1  6
 27 55  1  0
 27 56  1  0
 16 45  1  6
 17 46  1  0
 17 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  6
 21 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  0
  6 37  1  6
  7 38  1  0
  8 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
  5 36  1  1
  1 33  1  0
  1 34  1  0
  1 35  1  0
M  END


  Mrv1652309102222072D          

 32 34  0  0  1  0            999 V2000
    2.1434   -0.4125    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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   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
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -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 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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
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 20 26  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 28  1  0  0  0  0
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 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0304781

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@H](C\C=C\[C@H]2CC=CC(=O)O2)O[C@H](\C=C\C2=CC=CC=C2)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O7/c1-17(26)29-23-16-21(12-6-10-20-11-7-13-24(28)32-20)31-22(25(23)30-18(2)27)15-14-19-8-4-3-5-9-19/h3-10,13-15,20-23,25H,11-12,16H2,1-2H3/b10-6+,15-14+/t20-,21-,22+,23+,25+/m0/s1

> <INCHI_KEY>
BZDVLYSISKBBJQ-AIZKODKSSA-N

> <FORMULA>
C25H28O7

> <MOLECULAR_WEIGHT>
440.492

> <EXACT_MASS>
440.183503242

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
46.69483972124709

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,4R,6S)-3-(acetyloxy)-6-[(2E)-3-[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]prop-2-en-1-yl]-2-[(E)-2-phenylethenyl]oxan-4-yl acetate

> <JCHEM_LOGP>
3.617883896666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.514427327355094

> <JCHEM_PKA_STRONGEST_BASIC>
-4.213301458439755

> <JCHEM_POLAR_SURFACE_AREA>
88.13

> <JCHEM_REFRACTIVITY>
119.18570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,6S)-3-(acetyloxy)-6-[(2E)-3-[(2R)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(E)-2-phenylethenyl]oxan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.000  -4.620   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   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    6   16                                                       
CONECT   16   15   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   20                                                       
CONECT   27   16   28                                                       
CONECT   28   27    5   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
(2R,3S,4R,6S)-3-(Acetyloxy)-6-[(2E)-3-[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]prop-2-en-1-yl]-2-[(e)-2-phenylethenyl]oxan-4-yl acetic acid	Generator

Chemical Formula

C₂₅H₂₈O₇

Average Mass

440.4920 Da

Monoisotopic Mass

440.18350 Da

IUPAC Name

(2R,3S,4R,6S)-3-(acetyloxy)-6-[(2E)-3-[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]prop-2-en-1-yl]-2-[(E)-2-phenylethenyl]oxan-4-yl acetate

Traditional Name

(2R,3S,4R,6S)-3-(acetyloxy)-6-[(2E)-3-[(2R)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(E)-2-phenylethenyl]oxan-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@H](C\C=C\[C@H]2CC=CC(=O)O2)O[C@H](\C=C\C2=CC=CC=C2)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C25H28O7/c1-17(26)29-23-16-21(12-6-10-20-11-7-13-24(28)32-20)31-22(25(23)30-18(2)27)15-14-19-8-4-3-5-9-19/h3-10,13-15,20-23,25H,11-12,16H2,1-2H3/b10-6+,15-14+/t20-,21-,22+,23+,25+/m0/s1

InChI Key

BZDVLYSISKBBJQ-AIZKODKSSA-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
Cryptocarya moschata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

C-glycosyl compound
Tricarboxylic acid or derivatives
Styrene
Dihydropyranone
Benzenoid
Pyran
Oxane
Monosaccharide
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.62	ChemAxon
pKa (Strongest Acidic)	17.51	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.13 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	119.19 m³·mol⁻¹	ChemAxon
Polarizability	46.69 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

32055226

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162820267

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4r,6s)-3-(acetyloxy)-6-[(2e)-3-[(2r)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(1e)-2-phenylethenyl]oxan-4-yl acetate (NP0304781)

MOL for NP0304781 ((2r,3s,4r,6s)-3-(acetyloxy)-6-[(2e)-3-[(2r)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(1e)-2-phenylethenyl]oxan-4-yl acetate)

3D MOL for NP0304781 ((2r,3s,4r,6s)-3-(acetyloxy)-6-[(2e)-3-[(2r)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(1e)-2-phenylethenyl]oxan-4-yl acetate)

3D SDF for NP0304781 ((2r,3s,4r,6s)-3-(acetyloxy)-6-[(2e)-3-[(2r)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(1e)-2-phenylethenyl]oxan-4-yl acetate)

3D-SDF for NP0304781 ((2r,3s,4r,6s)-3-(acetyloxy)-6-[(2e)-3-[(2r)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(1e)-2-phenylethenyl]oxan-4-yl acetate)

PDB for NP0304781 ((2r,3s,4r,6s)-3-(acetyloxy)-6-[(2e)-3-[(2r)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(1e)-2-phenylethenyl]oxan-4-yl acetate)

3D PDB for NP0304781 ((2r,3s,4r,6s)-3-(acetyloxy)-6-[(2e)-3-[(2r)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(1e)-2-phenylethenyl]oxan-4-yl acetate)

SMILES for NP0304781 ((2r,3s,4r,6s)-3-(acetyloxy)-6-[(2e)-3-[(2r)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(1e)-2-phenylethenyl]oxan-4-yl acetate)

INCHI for NP0304781 ((2r,3s,4r,6s)-3-(acetyloxy)-6-[(2e)-3-[(2r)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(1e)-2-phenylethenyl]oxan-4-yl acetate)

Structure for NP0304781 ((2r,3s,4r,6s)-3-(acetyloxy)-6-[(2e)-3-[(2r)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(1e)-2-phenylethenyl]oxan-4-yl acetate)

3D Structure for NP0304781 ((2r,3s,4r,6s)-3-(acetyloxy)-6-[(2e)-3-[(2r)-6-oxo-2,3-dihydropyran-2-yl]prop-2-en-1-yl]-2-[(1e)-2-phenylethenyl]oxan-4-yl acetate)