NP-MRD: Showing NP-Card for methyl (1's,2r,2's,4's,6's,7's)-4-[(1s)-1-hydroxyethyl]-5-oxo-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate (NP0297178)

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Record Information

Version

2.0

Created at

2022-09-10 07:16:25 UTC

Updated at

2022-09-10 07:16:25 UTC

NP-MRD ID

NP0297178

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1's,2r,2's,4's,6's,7's)-4-[(1s)-1-hydroxyethyl]-5-oxo-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate

Description

Plumiepoxide belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. methyl (1's,2r,2's,4's,6's,7's)-4-[(1s)-1-hydroxyethyl]-5-oxo-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate is found in Allamanda schottii. Based on a literature review very few articles have been published on Plumiepoxide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102209162D          

 34 38  0  0  1  0            999 V2000
    6.7454    2.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4348    2.9366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6176    3.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3069    3.8140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1110    2.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4217    1.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    0.9831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0979    1.0962    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5913    0.4450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9020   -0.3192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7192   -0.4323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0299   -1.1966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8471   -1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3536   -0.6586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5233   -1.8478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8339   -2.6121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061   -1.7347    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1995   -2.3859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3954   -0.9704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5782   -0.8573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872    1.8605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2938    2.5117    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8310    3.1946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2364    3.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0385    2.9656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0114    2.1410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9843    1.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918    1.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9112    0.3116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0991    0.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4429   -0.3193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7290    1.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9045    1.7975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2356    2.4216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22  5  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 25 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  1  0  0  0
 28 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 26 34  1  1  0  0  0
M  END

     RDKit          3D

 60 64  0  0  0  0  0  0  0  0999 V2000
   -2.5194    6.3377    3.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7662    5.3294    2.9449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3609    4.2126    2.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6097    4.1144    2.5328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5565    3.1942    1.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2489    3.3654    1.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4928    2.4187    1.0358 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0076    1.2045    0.4537 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9393    0.2249    0.7931 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7584   -0.1707   -0.2606 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7236   -1.5297   -0.5214 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7678   -1.8359   -1.3824 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4880   -3.0309   -2.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291   -4.1932   -1.5753 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0725   -1.9950   -0.6359 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1663   -1.7007   -1.4724 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0346   -0.9795    0.4873 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5273   -1.5723    1.6478 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2078    0.2010    0.0545 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8495    0.8170   -1.0104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3526    0.8539    0.8573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2443    2.0303    1.2014 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8912    2.4338   -0.1195 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0949    1.8158   -0.4443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7894    1.3675   -0.9891 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2280    0.1826   -0.1801 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5986   -0.8068   -1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2861   -1.9323   -0.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0067   -3.2340   -1.6531 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7592   -4.3609   -0.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9052   -3.0588   -2.4715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4121   -1.7374   -0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2904   -2.6270    0.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3362   -0.4447    0.3960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8694    6.9822    4.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3470    5.8721    4.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9127    6.9999    2.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042    4.2419    2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0837    1.3867   -0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5283    0.3500   -1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9089   -0.9765   -2.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7302   -2.7512   -3.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4155   -3.2486   -2.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825   -4.6978   -1.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2295   -3.0257   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7650   -1.0347   -1.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0572   -0.5925    0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2148   -2.4804    1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2331    0.9597    0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6169    1.3179   -0.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3399    0.1923    1.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0682    1.7439    1.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8222    3.5009   -0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8945    1.2308   -2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7100   -0.7620   -1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8677   -3.5091   -2.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5326   -5.1688   -0.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7286   -4.0670    0.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7863   -4.8896   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1987   -2.4686   -3.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 34  1  1
 34 32  1  0
 32 33  2  0
 32 28  1  0
 28 27  2  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 22  5  1  0
 25 23  1  0
 27 26  1  0
 19 10  1  0
 26 21  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  6 38  1  0
  8 39  1  6
 10 40  1  6
 12 41  1  6
 13 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  1
 16 46  1  0
 17 47  1  1
 18 48  1  0
 19 49  1  1
 20 50  1  0
 21 51  1  1
 22 52  1  1
 23 53  1  6
 25 54  1  6
 27 55  1  0
 29 56  1  6
 30 57  1  0
 30 58  1  0
 30 59  1  0
 31 60  1  0
M  END


  Mrv1652309102209162D          

 34 38  0  0  1  0            999 V2000
    6.7454    2.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4348    2.9366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6176    3.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3069    3.8140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1110    2.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4217    1.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    0.9831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0979    1.0962    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5913    0.4450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9020   -0.3192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7192   -0.4323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0299   -1.1966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8471   -1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3536   -0.6586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5233   -1.8478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8339   -2.6121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061   -1.7347    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1995   -2.3859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3954   -0.9704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5782   -0.8573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872    1.8605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2938    2.5117    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8310    3.1946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2364    3.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0385    2.9656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0114    2.1410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9843    1.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918    1.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9112    0.3116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0991    0.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4429   -0.3193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7290    1.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9045    1.7975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2356    2.4216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22  5  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 25 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  1  0  0  0
 28 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 26 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0297178

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]2[C@@H]1[C@@H]1O[C@@H]1[C@]21OC(=O)C(=C1)[C@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O13/c1-6(23)7-3-21(34-18(7)28)11-10(15-16(21)32-15)8(17(27)29-2)5-30-19(11)33-20-14(26)13(25)12(24)9(4-22)31-20/h3,5-6,9-16,19-20,22-26H,4H2,1-2H3/t6-,9+,10+,11+,12+,13-,14+,15-,16-,19-,20-,21+/m0/s1

> <INCHI_KEY>
UQXYPTGJEROWIM-NQPMCGTESA-N

> <FORMULA>
C21H26O13

> <MOLECULAR_WEIGHT>
486.426

> <EXACT_MASS>
486.137340897

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
45.60896821686008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1'S,2R,2'S,4'S,6'S,7'S)-4-[(1S)-1-hydroxyethyl]-5-oxo-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5H-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0^{2,4}]decan]-9'-ene-10'-carboxylate

> <JCHEM_LOGP>
-2.3408733230000003

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.184990914457753

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.205442955767515

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9547004300309814

> <JCHEM_POLAR_SURFACE_AREA>
193.97

> <JCHEM_REFRACTIVITY>
105.20419999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1'S,2R,2'S,4'S,6'S,7'S)-4-[(1S)-1-hydroxyethyl]-5-oxo-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0^{2,4}]decan]-9'-ene-10'-carboxylate

> <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      12.591   4.055   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.012   5.482   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.486   5.693   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.906   7.119   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.541   4.477   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.120   3.051   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.175   1.835   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.649   2.046   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.704   0.831   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.284  -0.596   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.809  -0.807   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.389  -2.234   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.915  -2.445   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.860  -1.229   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.443  -3.449   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.023  -4.876   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.918  -3.238   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.972  -4.454   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.338  -1.811   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.813  -1.600   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.070   3.473   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.015   4.688   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.151   5.963   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.041   7.031   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.672   5.536   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.621   3.997   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.571   2.457   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.091   2.030   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.568   0.582   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.052   0.311   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.560  -0.596   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.228   3.305   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.688   3.355   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.173   4.520   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   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22   26                                                  
CONECT   22   21    5   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   25                                                       
CONECT   25   24   23   26                                                  
CONECT   26   25   21   27   34                                             
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   28   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   26                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆O₁₃

Average Mass

486.4260 Da

Monoisotopic Mass

486.13734 Da

IUPAC Name

methyl (1'S,2R,2'S,4'S,6'S,7'S)-4-[(1S)-1-hydroxyethyl]-5-oxo-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5H-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0^{2,4}]decan]-9'-ene-10'-carboxylate

Traditional Name

methyl (1'S,2R,2'S,4'S,6'S,7'S)-4-[(1S)-1-hydroxyethyl]-5-oxo-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0^{2,4}]decan]-9'-ene-10'-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]2[C@@H]1[C@@H]1O[C@@H]1[C@]21OC(=O)C(=C1)[C@H](C)O

InChI Identifier

InChI=1S/C21H26O13/c1-6(23)7-3-21(34-18(7)28)11-10(15-16(21)32-15)8(17(27)29-2)5-30-19(11)33-20-14(26)13(25)12(24)9(4-22)31-20/h3,5-6,9-16,19-20,22-26H,4H2,1-2H3/t6-,9+,10+,11+,12+,13-,14+,15-,16-,19-,20-,21+/m0/s1

InChI Key

UQXYPTGJEROWIM-NQPMCGTESA-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
Allamanda neriifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
2-furanone
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Dihydrofuran
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Lactone
Polyol
Carboxylic acid derivative
Dialkyl ether
Acetal
Oxirane
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Organic oxide
Alcohol
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	-2.3	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	193.97 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	105.2 m³·mol⁻¹	ChemAxon
Polarizability	45.61 Å³	ChemAxon
Number of Rings	5	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

C00010740

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

101423564

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1's,2r,2's,4's,6's,7's)-4-[(1s)-1-hydroxyethyl]-5-oxo-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate (NP0297178)

MOL for NP0297178 (methyl (1's,2r,2's,4's,6's,7's)-4-[(1s)-1-hydroxyethyl]-5-oxo-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

3D MOL for NP0297178 (methyl (1's,2r,2's,4's,6's,7's)-4-[(1s)-1-hydroxyethyl]-5-oxo-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

3D SDF for NP0297178 (methyl (1's,2r,2's,4's,6's,7's)-4-[(1s)-1-hydroxyethyl]-5-oxo-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

3D-SDF for NP0297178 (methyl (1's,2r,2's,4's,6's,7's)-4-[(1s)-1-hydroxyethyl]-5-oxo-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

PDB for NP0297178 (methyl (1's,2r,2's,4's,6's,7's)-4-[(1s)-1-hydroxyethyl]-5-oxo-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

3D PDB for NP0297178 (methyl (1's,2r,2's,4's,6's,7's)-4-[(1s)-1-hydroxyethyl]-5-oxo-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

SMILES for NP0297178 (methyl (1's,2r,2's,4's,6's,7's)-4-[(1s)-1-hydroxyethyl]-5-oxo-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

INCHI for NP0297178 (methyl (1's,2r,2's,4's,6's,7's)-4-[(1s)-1-hydroxyethyl]-5-oxo-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

Structure for NP0297178 (methyl (1's,2r,2's,4's,6's,7's)-4-[(1s)-1-hydroxyethyl]-5-oxo-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

3D Structure for NP0297178 (methyl (1's,2r,2's,4's,6's,7's)-4-[(1s)-1-hydroxyethyl]-5-oxo-7'-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[furan-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)