NP-MRD: Showing NP-Card for 6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate (NP0291346)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 22:24:02 UTC

Updated at

2022-09-09 22:24:02 UTC

NP-MRD ID

NP0291346

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

Description

6-Methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate 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. 6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate is found in Lactuca serriola. 6-Methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161508492D          

 41 45  0  0  0  0            999 V2000
    3.6754    3.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    2.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    1.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    0.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    2.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    2.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    3.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988    3.7963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217    4.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897    4.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    5.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997    5.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    6.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    7.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456    7.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686    8.3896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906    7.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    6.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749    2.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    0.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882   -0.2656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0983   -1.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6222   -1.6752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3324   -2.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8563   -3.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6702   -2.9497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185   -2.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286   -3.3551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945   -1.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1807   -2.0807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2844   -1.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -0.5359    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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  2  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 31 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END

     RDKit          3D

 73 77  0  0  0  0  0  0  0  0999 V2000
    0.5144   -1.6713    2.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3981   -0.5510    1.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    0.3991    1.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4940    0.5121    2.4450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7448    1.1174    0.2585 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886    0.6731   -0.5758 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3736   -0.3533   -1.4988 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4378    0.2975   -2.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6905    0.9603   -1.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4329   -0.0157   -1.0797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6309    0.4808   -0.6038 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6674   -0.0626   -1.3921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8676    0.5860   -1.2194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9193    1.9544   -1.8893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1987    2.5031   -1.6503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2102    0.7341    0.2625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.5625    0.4599    0.5076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3201   -0.2181    1.0187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6699   -0.3315    2.3535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8824    0.2667    0.8522 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0638   -0.7443    1.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760    0.2473   -3.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727   -0.4430   -3.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6554   -0.6872   -4.8870 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5770   -0.8353   -2.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6982   -1.5038   -2.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4613   -1.8648   -3.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1844   -1.8704   -0.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4281   -0.6394   -0.0753 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2470   -0.9687    1.0326 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5660   -0.5606    1.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0283    0.1341    0.2180 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4263   -0.9025    2.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7751   -0.3250    2.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1208    0.9505    2.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3693    1.4392    2.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3378    0.6850    1.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6291    1.1776    1.3477 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9848   -0.5878    1.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7366   -1.1164    1.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2809    0.1306    0.3678 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3437   -2.3570    1.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2731   -1.9564    2.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941    1.5178   -1.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7949   -1.1304   -0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3186    1.2976   -2.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4799    1.8382   -1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6495    1.5612   -0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6686   -0.0467   -1.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1987    2.6669   -1.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7811    1.8913   -2.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1874    3.4232   -2.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9512    1.7572    0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0835    1.0240   -0.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3598   -1.2001    0.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9391   -1.2734    2.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7527    1.1614    1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2762   -0.7553    2.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7797    0.6540   -4.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3241   -2.4861   -3.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7971   -0.9836   -4.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8293   -2.5579   -4.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3930   -2.4740   -0.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0913   -2.4739   -0.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0761    0.0037   -0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4645   -1.9936    2.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0246   -0.3992    3.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3436    1.5483    2.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6357    2.4498    2.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8447    2.1024    1.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7595   -1.1816    0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4996   -2.1283    1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6462    1.0441    0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26 25  2  0
 25  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 41  1  0
 41 29  1  0
 29 28  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 37 39  1  0
 39 40  2  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
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  8 22  2  0
 22 23  1  0
 23 24  2  0
 28 26  1  0
 40 34  1  0
 20 11  1  0
 23 25  1  0
 41  6  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
  7 45  1  1
  6 44  1  6
  1 42  1  0
  1 43  1  0
 41 73  1  1
 29 65  1  6
 28 63  1  0
 28 64  1  0
 33 66  1  0
 33 67  1  0
 35 68  1  0
 36 69  1  0
 38 70  1  0
 39 71  1  0
 40 72  1  0
  9 46  1  0
  9 47  1  0
 11 48  1  1
 13 49  1  6
 14 50  1  0
 14 51  1  0
 15 52  1  0
 16 53  1  1
 17 54  1  0
 18 55  1  6
 19 56  1  0
 20 57  1  1
 21 58  1  0
 22 59  1  0
M  END


  Mrv1533004161508492D          

 41 45  0  0  0  0            999 V2000
    3.6754    3.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    2.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    1.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    0.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    2.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    2.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    3.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988    3.7963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217    4.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897    4.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    5.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997    5.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    6.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    7.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456    7.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686    8.3896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906    7.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    6.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749    2.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    0.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882   -0.2656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0983   -1.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6222   -1.6752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3324   -2.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8563   -3.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6702   -2.9497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185   -2.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286   -3.3551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945   -1.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1807   -2.0807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2844   -1.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -0.5359    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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  2  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 31 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291346

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2C(C3OC(=O)C(=C)C3C(C1)OC(=O)CC1=CC=C(O)C=C1)C(COC1OC(CO)C(O)C(O)C1O)=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H32O12/c1-12-7-18(39-20(33)8-14-3-5-16(31)6-4-14)22-13(2)28(37)41-27(22)23-15(9-17(32)21(12)23)11-38-29-26(36)25(35)24(34)19(10-30)40-29/h3-6,9,18-19,22-27,29-31,34-36H,2,7-8,10-11H2,1H3

> <INCHI_KEY>
HCOZTDACWSVSLP-UHFFFAOYSA-N

> <FORMULA>
C29H32O12

> <MOLECULAR_WEIGHT>
572.563

> <EXACT_MASS>
572.18937647

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
56.78698444695557

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
0.1833231430000009

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.133178548876645

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.495420705346477

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835523219152

> <JCHEM_POLAR_SURFACE_AREA>
189.27999999999997

> <JCHEM_REFRACTIVITY>
140.13270000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       6.861   7.086   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.657   6.126   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.999   4.625   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.039   3.421   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.499   3.421   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.651   2.136   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.166   2.545   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.038   1.585   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.097   4.084   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.188   4.932   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.539   4.625   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.882   6.126   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.269   6.794   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.678   7.086   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.907   8.609   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.341   9.172   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.703   9.569   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.933  11.092   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.271  12.052   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.042  13.575   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.392  14.138   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.621  15.661   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.596  13.178   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.366  11.655   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.888   2.136   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.372   2.545   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.441   4.084   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.726   4.932   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.346   0.694   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.325  -0.496   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.783  -1.938   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.762  -3.127   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.220  -4.569   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.198  -5.758   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.718  -5.506   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.701  -4.821   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.160  -6.263   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.723  -3.632   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.204  -3.884   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       4.264  -2.190   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       3.286  -1.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4   27                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    2                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25    4   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26    3   28                                                  
CONECT   28   27                                                            
CONECT   29   25   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   40                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   31   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
6-Methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3ah,4H,5H,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetic acid	Generator

Chemical Formula

C₂₉H₃₂O₁₂

Average Mass

572.5630 Da

Monoisotopic Mass

572.18938 Da

IUPAC Name

6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

Traditional Name

6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

CAS Registry Number

Not Available

SMILES

CC1=C2C(C3OC(=O)C(=C)C3C(C1)OC(=O)CC1=CC=C(O)C=C1)C(COC1OC(CO)C(O)C(O)C1O)=CC2=O

InChI Identifier

InChI=1S/C29H32O12/c1-12-7-18(39-20(33)8-14-3-5-16(31)6-4-14)22-13(2)28(37)41-27(22)23-15(9-17(32)21(12)23)11-38-29-26(36)25(35)24(34)19(10-30)40-29/h3-6,9,18-19,22-27,29-31,34-36H,2,7-8,10-11H2,1H3

InChI Key

HCOZTDACWSVSLP-UHFFFAOYSA-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
Lactuca serriola	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
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Gamma butyrolactone
Monosaccharide
Oxane
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Ketone
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Polyol
Oxacycle
Carboxylic acid derivative
Acetal
Primary alcohol
Alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.21	ALOGPS
logP	0.18	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	140.13 m³·mol⁻¹	ChemAxon
Polarizability	56.79 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate (NP0291346)

MOL for NP0291346 (6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

3D MOL for NP0291346 (6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

3D SDF for NP0291346 (6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

3D-SDF for NP0291346 (6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

PDB for NP0291346 (6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

3D PDB for NP0291346 (6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

SMILES for NP0291346 (6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

INCHI for NP0291346 (6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

Structure for NP0291346 (6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)

3D Structure for NP0291346 (6-methyl-3-methylidene-2,7-dioxo-9-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate)