NP-MRD: Showing NP-Card for Lactucopicrin-15-oxalate (NP0073604)

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Record Information

Version

2.0

Created at

2022-04-28 18:49:42 UTC

Updated at

2022-04-28 18:49:42 UTC

NP-MRD ID

NP0073604

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lactucopicrin-15-oxalate

Description

Lactucopicrin 15-oxalate, also known as 15-oxalyllactucopicrin, belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Lactucopicrin 15-oxalate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Lactucopicrin-15-oxalate is found in Lactuca sativa L. . Lactucopicrin-15-oxalate was first documented in 2018 (PMID: 29997631). Based on a literature review very few articles have been published on lactucopicrin 15-oxalate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220492D          

 35 38  0  0  1  0            999 V2000
    3.6659   -0.2370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1803   -0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967   -1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534   -2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101   -1.6863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3265   -0.8820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8409   -0.2370    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3864    0.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461    0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656   -1.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651   -2.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881   -3.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560   -3.3179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431   -3.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660   -4.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2340   -4.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3569   -5.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7119   -5.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440   -5.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210   -4.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8349   -6.7940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -2.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412   -1.0466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305    1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3545    1.8612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0646    2.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2508    2.7687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5886    3.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2987    4.0432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4024    3.1357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  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
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 11  1  1  0  0  0
 11 12  2  0  0  0  0
  5 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
  3 24  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
  1 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    0.9683    2.8674    1.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1261    2.2644    1.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2512    3.0186    0.7839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3098    4.2294    0.4546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2888    2.0908    0.6475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847    0.8473    0.3515 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6032   -0.2805    0.6408 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8273   -0.1942   -0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7613    0.9814   -0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8373    0.7365   -1.0372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8091   -0.2396   -0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7320   -0.9729    0.1494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8863   -0.4276   -1.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9681    0.2978   -2.8245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8262   -1.4083   -1.6025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9922   -1.2951   -0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8931   -2.2531   -0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7748   -3.4095   -1.1594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0212   -1.6029    0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905   -2.1522    0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520   -3.4990    0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0699   -1.4734    1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5105   -0.1415    1.0075 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7608    0.2185    1.4847 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8990    0.2578    0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7239   -0.0537   -0.5379 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1926    0.6498    1.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2385    0.6187    0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9262   -0.5548   -0.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8987   -0.5860   -0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1958    0.5196   -1.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1866    0.4705   -2.7350 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4866    1.6875   -1.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5070    1.7296   -0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5173    0.8651    1.3554 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0417    3.9419    1.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8152    2.3790    2.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226    0.9001   -0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462   -0.2392    1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0531    1.2494    0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2435    1.8967   -0.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6802   -2.3906   -1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8039   -1.4979   -1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3641   -4.2400    0.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3854   -3.5067   -0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3525   -3.8807    0.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4697   -1.1978    2.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9275   -2.0920    1.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493   -0.3762   -0.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4804   -0.0538    2.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1381    1.6607    1.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7073   -1.4295    0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4870   -1.4911   -1.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1245    0.7118   -2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6839    2.5750   -2.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9402    2.6378   -0.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9910    0.6367    2.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 19  2  0
 19  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 35  1  0
 35 23  1  0
 23 22  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 15  1  0
 13 14  2  0
  8 16  2  0
 16 17  1  0
 17 18  2  0
 22 20  1  0
 34 28  1  0
 17 19  1  0
 35  6  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
  7 39  1  1
  6 38  1  6
  1 36  1  0
  1 37  1  0
 35 57  1  1
 23 49  1  6
 22 47  1  0
 22 48  1  0
 27 50  1  0
 27 51  1  0
 29 52  1  0
 30 53  1  0
 32 54  1  0
 33 55  1  0
 34 56  1  0
  9 40  1  0
  9 41  1  0
 15 42  1  0
 16 43  1  0
M  END


  Mrv1652304282220492D          

 35 38  0  0  1  0            999 V2000
    3.6659   -0.2370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1803   -0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967   -1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534   -2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101   -1.6863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3265   -0.8820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8409   -0.2370    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3864    0.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461    0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656   -1.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651   -2.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881   -3.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560   -3.3179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431   -3.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660   -4.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2340   -4.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3569   -5.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7119   -5.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440   -5.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210   -4.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8349   -6.7940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -2.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412   -1.0466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305    1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3545    1.8612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0646    2.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2508    2.7687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5886    3.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2987    4.0432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4024    3.1357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  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
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 11  1  1  0  0  0
 11 12  2  0  0  0  0
  5 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
  3 24  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
  1 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073604

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2[C@@H]([C@H]3OC(=O)C(=C)[C@@H]3[C@H](C1)OC(=O)CC1=CC=C(O)C=C1)C(COC(=O)C(O)=O)=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H22O10/c1-11-7-17(34-18(28)8-13-3-5-15(26)6-4-13)20-12(2)24(31)35-22(20)21-14(9-16(27)19(11)21)10-33-25(32)23(29)30/h3-6,9,17,20-22,26H,2,7-8,10H2,1H3,(H,29,30)/t17-,20+,21-,22-/m0/s1

> <INCHI_KEY>
AUULYUITRYGGJX-XGARDCMYSA-N

> <FORMULA>
C25H22O10

> <MOLECULAR_WEIGHT>
482.441

> <EXACT_MASS>
482.121296908

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
47.68778933288759

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aR,4S,9aS,9bR)-9-{[(carboxycarbonyl)oxy]methyl}-6-methyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
2.5882116773333332

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.49622446127988

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2062432265129126

> <JCHEM_PKA_STRONGEST_BASIC>
-5.958556506857307

> <JCHEM_POLAR_SURFACE_AREA>
153.5

> <JCHEM_REFRACTIVITY>
118.66579999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,9aS,9bR)-9-{[(carboxycarbonyl)oxy]methyl}-6-methyl-3-methylidene-2,7-dioxo-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl (4-hydroxyphenyl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.843  -0.442   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.803  -1.646   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.461  -3.148   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.073  -3.816   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.686  -3.148   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.343  -1.646   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.303  -0.442   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.455   0.843   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.970   0.433   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.766   1.393   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.901  -1.105   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.616  -1.954   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.482  -4.108   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.711  -5.631   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.145  -6.193   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.507  -6.591   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.737  -8.114   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.170  -8.676   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.400 -10.199   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.196 -11.159   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.762 -10.597   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.533  -9.074   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.425 -12.682   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.665  -4.108   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.245  -1.105   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.530  -1.954   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.176   0.433   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.691   0.843   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.150   2.285   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.128   3.474   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.587   4.916   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.068   5.168   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.565   6.106   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.024   7.547   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      10.085   5.853   0.000  0.00  0.00           O+0
CONECT    1    2    7   28                                                  
CONECT    2    1    3   25                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    6   12                                                  
CONECT   12   11                                                            
CONECT   13    5   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   20                                                            
CONECT   24    3                                                            
CONECT   25    2   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27    1   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
15-Oxalyllactucopicrin	ChEBI
Lactucopicrin-15-oxalate	ChEBI
Lactucopicrin-15-oxalic acid	Generator
Lactucopicrin 15-oxalic acid	Generator

Chemical Formula

C₂₅H₂₂O₁₀

Average Mass

482.4410 Da

Monoisotopic Mass

482.12130 Da

IUPAC Name

(3aR,4S,9aS,9bR)-9-{[(carboxycarbonyl)oxy]methyl}-6-methyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

Traditional Name

(3aR,4S,9aS,9bR)-9-{[(carboxycarbonyl)oxy]methyl}-6-methyl-3-methylidene-2,7-dioxo-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl (4-hydroxyphenyl)acetate

CAS Registry Number

Not Available

SMILES

CC1=C2[C@@H]([C@H]3OC(=O)C(=C)[C@@H]3[C@H](C1)OC(=O)CC1=CC=C(O)C=C1)C(COC(=O)C(O)=O)=CC2=O

InChI Identifier

InChI=1S/C25H22O10/c1-11-7-17(34-18(28)8-13-3-5-15(26)6-4-13)20-12(2)24(31)35-22(20)21-14(9-16(27)19(11)21)10-33-25(32)23(29)30/h3-6,9,17,20-22,26H,2,7-8,10H2,1H3,(H,29,30)/t17-,20+,21-,22-/m0/s1

InChI Key

AUULYUITRYGGJX-XGARDCMYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 sativa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Gamma butyrolactone
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Lactone
Ketone
Carboxylic acid ester
Carboxylic acid
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	2.42	ALOGPS
logP	2.59	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	2.21	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	153.5 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	118.67 m³·mol⁻¹	ChemAxon
Polarizability	47.69 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00034018

Chemspider ID

58145766

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102242110

PDB ID

Not Available

ChEBI ID

90280

Good Scents ID

Not Available

References

General References

Tamura Y, Mori T, Nakabayashi R, Kobayashi M, Saito K, Okazaki S, Wang N, Kusano M: Metabolomic Evaluation of the Quality of Leaf Lettuce Grown in Practical Plant Factory to Capture Metabolite Signature. Front Plant Sci. 2018 Jun 27;9:665. doi: 10.3389/fpls.2018.00665. eCollection 2018. [PubMed:29997631 ]

Showing NP-Card for Lactucopicrin-15-oxalate (NP0073604)

MOL for NP0073604 (Lactucopicrin-15-oxalate)

3D MOL for NP0073604 (Lactucopicrin-15-oxalate)

3D SDF for NP0073604 (Lactucopicrin-15-oxalate)

3D-SDF for NP0073604 (Lactucopicrin-15-oxalate)

PDB for NP0073604 (Lactucopicrin-15-oxalate)

3D PDB for NP0073604 (Lactucopicrin-15-oxalate)

SMILES for NP0073604 (Lactucopicrin-15-oxalate)

INCHI for NP0073604 (Lactucopicrin-15-oxalate)

Structure for NP0073604 (Lactucopicrin-15-oxalate)

3D Structure for NP0073604 (Lactucopicrin-15-oxalate)