NP-MRD: Showing NP-Card for (3s,3as,5r,9as,9bs)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione (NP0311848)

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Record Information

Version

2.0

Created at

2022-09-11 08:07:36 UTC

Updated at

2022-09-11 08:07:36 UTC

NP-MRD ID

NP0311848

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3as,5r,9as,9bs)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione

Description

(3s,3as,5r,9as,9bs)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione is found in Cichorium endivia.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241212182D          

 34 37  0  0  0  0            999 V2000
    0.3069    3.4846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0502    3.1267    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2337    2.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7194    1.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1056    1.6774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6200    2.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4364    3.1267    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7584    3.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3797    3.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0554    2.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0773    0.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785    1.5402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502    3.9517    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324    4.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1577    4.8464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156    4.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1961    4.3021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0065    3.7229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2332    2.9131    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8241    3.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9736    5.1927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3069    2.6596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1696   -0.3074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1696   -1.1324    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4551   -1.5449    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2594   -1.1324    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2594   -0.3074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4551    0.1051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4551    0.9301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9738    0.1051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840   -1.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4551   -2.3699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9739   -1.5449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840   -2.3699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  0  0  0  0
 10  3  1  0  0  0  0
  3  2  1  0  0  0  0
  8  2  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 11  1  0  0  0  0
 10 12  2  0  0  0  0
  2 13  1  6  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 17  1  1  0  0  0  0
  1  7  1  0  0  0  0
  7 18  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  7 19  1  6  0  0  0
 18 20  1  6  0  0  0
 16 21  2  0  0  0  0
  1 22  1  1  0  0  0
 23 24  1  0  0  0  0
 23 28  1  0  0  0  0
 24 25  1  0  0  0  0
 24 31  1  1  0  0  0
 26 25  1  0  0  0  0
 25 32  1  6  0  0  0
 26 27  1  0  0  0  0
 26 33  1  1  0  0  0
 27 28  1  0  0  0  0
 27 30  1  6  0  0  0
 28 29  1  1  0  0  0
 31 34  1  0  0  0  0
  5 29  1  6  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
   -0.2883   -2.6180    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6223   -1.4819    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8670   -1.8626    0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3718   -3.2076    0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7226   -4.2658    0.1784 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8540   -3.1762   -0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2296   -1.8942   -0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6505   -1.4886   -0.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5184   -2.5718   -0.2164 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0913   -1.0154   -0.2625 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9480    0.1665    0.5753 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0704    0.9572    0.8774 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5366    2.1958    1.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1744    3.0484    1.9248 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1109    2.2801    0.8803 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7167    3.6345    0.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470    1.2416   -0.2105 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8819    0.7574   -0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0550   -0.0958    0.1459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2528   -0.0639   -0.2681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0811    0.5825    0.6472 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0213   -0.2759    1.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3240    0.0055    0.7685 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1136   -1.2932    0.9023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5183   -2.2104    0.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5040    0.4770   -0.6503 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8373    0.8856   -0.7820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6443    1.6797   -0.9779 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0303    1.4958   -2.2219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6287    1.8770    0.0960 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1195    2.6256    1.1738 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0159   -3.1876    1.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3341   -2.3046    0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2953   -3.3035   -0.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4697   -4.0620    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8753   -0.7477    0.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8281   -0.9888   -1.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4518   -3.0608    0.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9629   -0.7260   -1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4388   -0.0357    1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4956    1.8856    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6102    3.7502    0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2015    4.4260    0.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8575    3.7534   -0.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8779    1.5913   -0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1165    0.1462   -1.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3076    1.6254   -1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0954    0.3843    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4455    0.9054    1.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7418    0.7084    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9003   -1.7263    1.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1804   -1.1633    0.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0273   -2.2571   -0.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3219   -0.3072   -1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4712    0.1527   -0.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2440    2.6094   -1.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4223    0.7169   -2.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752    2.4470   -0.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6502    2.3789    2.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 19  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 11 17  1  0
 15 17  1  0
 30 21  1  0
 10  3  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  1
 21 49  1  1
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 30 58  1  6
 31 59  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  6
 11 40  1  1
 15 41  1  1
 16 42  1  0
 16 43  1  0
 16 44  1  0
M  END


  Mrv0541 02241212182D          

 34 37  0  0  0  0            999 V2000
    0.3069    3.4846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0502    3.1267    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2337    2.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7194    1.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1056    1.6774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6200    2.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4364    3.1267    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7584    3.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3797    3.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0554    2.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0773    0.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785    1.5402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502    3.9517    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324    4.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1577    4.8464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156    4.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1961    4.3021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0065    3.7229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2332    2.9131    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8241    3.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9736    5.1927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1696   -0.3074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1696   -1.1324    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4551   -1.5449    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2594   -1.1324    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2594   -0.3074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4551    0.1051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4551    0.9301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9738    0.1051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840   -1.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4551   -2.3699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9739   -1.5449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840   -2.3699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  0  0  0  0
 10  3  1  0  0  0  0
  3  2  1  0  0  0  0
  8  2  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 11  1  0  0  0  0
 10 12  2  0  0  0  0
  2 13  1  6  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 17  1  1  0  0  0  0
  1  7  1  0  0  0  0
  7 18  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  7 19  1  6  0  0  0
 18 20  1  6  0  0  0
 16 21  2  0  0  0  0
  1 22  1  1  0  0  0
 23 24  1  0  0  0  0
 23 28  1  0  0  0  0
 24 25  1  0  0  0  0
 24 31  1  1  0  0  0
 26 25  1  0  0  0  0
 25 32  1  6  0  0  0
 26 27  1  0  0  0  0
 26 33  1  1  0  0  0
 27 28  1  0  0  0  0
 27 30  1  6  0  0  0
 28 29  1  1  0  0  0
 31 34  1  0  0  0  0
  5 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0311848

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(C)=C3C(=O)C=C(CO)[C@]3([H])[C@@]1([H])OC(=O)[C@H]2C

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O10/c1-7-10-4-12(29-21-18(27)17(26)16(25)13(6-23)30-21)8(2)14-11(24)3-9(5-22)15(14)19(10)31-20(7)28/h3,7,10,12-13,15-19,21-23,25-27H,4-6H2,1-2H3/t7-,10-,12+,13+,15-,16+,17-,18+,19-,21+/m0/s1

> <INCHI_KEY>
NKRBYIJSKJPAKV-NLHHRKRESA-N

> <FORMULA>
C21H28O10

> <MOLECULAR_WEIGHT>
440.441

> <EXACT_MASS>
440.168247116

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
43.78435193301024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,3aS,5R,9aS,9bS)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

> <ALOGPS_LOGP>
-0.96

> <JCHEM_LOGP>
-1.815880736666666

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.964465348294873

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.172914468642421

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7605694742203584

> <JCHEM_POLAR_SURFACE_AREA>
162.98

> <JCHEM_REFRACTIVITY>
104.41979999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aS,5R,9aS,9bS)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.573   6.505   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.960   5.837   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.303   4.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.343   3.131   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.197   3.131   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.157   4.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.815   5.837   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.282   6.626   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.442   5.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.837   4.197   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.011   1.744   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.627   2.875   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0       1.960   7.377   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       3.420   8.160   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.161   9.047   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.149   8.306   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.366   8.031   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.879   6.949   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0      -2.302   5.438   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0      -3.405   6.743   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.817   9.693   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       0.573   4.965   0.000  0.00  0.00           H+0
HETATM   23  O   UNK     0      -2.183  -0.574   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.183  -2.114   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.850  -2.884   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.484  -2.114   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.484  -0.574   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.850   0.196   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.850   1.736   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.818   0.196   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -3.517  -2.884   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.850  -4.424   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.818  -2.884   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -3.517  -4.424   0.000  0.00  0.00           O+0
CONECT    1    2   17    7   22                                             
CONECT    2    1    3    8   13                                             
CONECT    3    4   10    2                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1   18   19                                             
CONECT    8    2    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    3    9   12                                                  
CONECT   11    4                                                            
CONECT   12   10                                                            
CONECT   13    2                                                            
CONECT   14    8   15                                                       
CONECT   15   14                                                            
CONECT   16   17   18   21                                                  
CONECT   17    1   16                                                       
CONECT   18    7   16   20                                                  
CONECT   19    7                                                            
CONECT   20   18                                                            
CONECT   21   16                                                            
CONECT   22    1                                                            
CONECT   23   24   28                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26   32                                                  
CONECT   26   25   27   33                                                  
CONECT   27   26   28   30                                                  
CONECT   28   23   27   29                                                  
CONECT   29   28    5                                                       
CONECT   30   27                                                            
CONECT   31   24   34                                                       
CONECT   32   25                                                            
CONECT   33   26                                                            
CONECT   34   31                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₁₀

Average Mass

440.4410 Da

Monoisotopic Mass

440.16825 Da

IUPAC Name

(3S,3aS,5R,9aS,9bS)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

Traditional Name

(3S,3aS,5R,9aS,9bS)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(C)=C3C(=O)C=C(CO)[C@]3([H])[C@@]1([H])OC(=O)[C@H]2C

InChI Identifier

InChI=1S/C21H28O10/c1-7-10-4-12(29-21-18(27)17(26)16(25)13(6-23)30-21)8(2)14-11(24)3-9(5-22)15(14)19(10)31-20(7)28/h3,7,10,12-13,15-19,21-23,25-27H,4-6H2,1-2H3/t7-,10-,12+,13+,15-,16+,17-,18+,19-,21+/m0/s1

InChI Key

NKRBYIJSKJPAKV-NLHHRKRESA-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
Cichorium endivia	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
Gamma butyrolactone
Monosaccharide
Oxane
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary 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	-0.96	ALOGPS
logP	-1.8	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.42 m³·mol⁻¹	ChemAxon
Polarizability	43.78 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001800

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

102476815

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,3as,5r,9as,9bs)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione (NP0311848)

MOL for NP0311848 ((3s,3as,5r,9as,9bs)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

3D MOL for NP0311848 ((3s,3as,5r,9as,9bs)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

3D SDF for NP0311848 ((3s,3as,5r,9as,9bs)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

3D-SDF for NP0311848 ((3s,3as,5r,9as,9bs)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

PDB for NP0311848 ((3s,3as,5r,9as,9bs)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

3D PDB for NP0311848 ((3s,3as,5r,9as,9bs)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

SMILES for NP0311848 ((3s,3as,5r,9as,9bs)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

INCHI for NP0311848 ((3s,3as,5r,9as,9bs)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

Structure for NP0311848 ((3s,3as,5r,9as,9bs)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

3D Structure for NP0311848 ((3s,3as,5r,9as,9bs)-9-(hydroxymethyl)-3,6-dimethyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)