NP-MRD: Showing NP-Card for 5,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-13-yl acetate (NP0281530)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 07:56:16 UTC

Updated at

2022-09-09 07:56:17 UTC

NP-MRD ID

NP0281530

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-13-yl acetate

Description

13,15-Bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]Octadec-17-en-5-yl acetate belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. 5,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-13-yl acetate is found in Erythropodium caribaeorum. 13,15-Bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]Octadec-17-en-5-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241501272D          

 38 41  0  0  0  0            999 V2000
    2.9732   -0.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8580    0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1814    1.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4253    0.8328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3587    1.9687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1797    2.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6694    2.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3393    3.4690    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.4893    2.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9790    3.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8194    1.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3091    2.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1290    2.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8052    1.7328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6187    3.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6393    1.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4591    1.6806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9694    1.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4797    0.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2995    0.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8099   -0.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3202   -1.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5003   -0.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0106   -1.6392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1702   -0.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4860    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829   -0.6756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5346   -1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2735   -1.8659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473   -1.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6599    0.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3297    1.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0708    0.5718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0202    0.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5694   -0.0619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6472    1.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5099    1.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7592    0.5065    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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 25 31  1  0  0  0  0
 19 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  2  0  0  0  0
 34 36  1  0  0  0  0
 32 37  1  0  0  0  0
  2 37  1  0  0  0  0
  6 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END

     RDKit          3D

 69 72  0  0  0  0  0  0  0  0999 V2000
   -3.2305   -1.7465   -0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0585   -0.7758   -0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3159   -1.0493    1.1063 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5074   -2.0999    2.0169 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0448   -1.7237    1.1173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8001   -2.8111    0.2750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4429   -3.2795    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112   -4.4509    0.5030 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1271   -2.2076    1.5024 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0327   -2.4296    2.9780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2638   -0.9982    1.0416 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3800    0.0081    1.9793 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8090   -0.6529   -0.3247 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1530   -1.1825   -0.4197 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565   -2.1420   -1.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9674   -2.5971   -1.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7193   -2.6110   -2.1198 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943    0.8216   -0.5891 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3583    1.2560   -0.9632 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8494    0.7949   -2.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2940    0.8316    0.0019 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3746    1.2219    1.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4004    0.6852    2.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656    2.0588    1.7343 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4191    2.7423   -1.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5430    3.2711   -1.2019 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1961    3.5057   -0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0054    2.9465   -1.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0928    1.4961   -1.3899 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0188    1.3744   -2.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3885    0.9104   -1.0087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6541    1.4738    0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473    1.5487   -0.7010 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6838    0.5702   -0.4396 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4968    1.0008    0.6315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8383    1.2665    0.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7647    1.7232    1.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3165    1.1232   -0.7598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8219   -2.7195   -0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7722   -1.6156   -1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2577   -0.1821    1.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0068   -2.2121    2.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1773   -2.0860    1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0439   -2.3482    3.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159   -3.4786    3.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -1.7199    3.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1472   -0.1071    2.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2885   -1.2067   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3297   -2.8760   -2.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6550   -1.7886   -0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0545   -3.4637   -0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8333    1.2759    0.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2047    0.1515   -2.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1374    1.6797   -2.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8214    0.2780   -2.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7743    1.5523    2.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2608    0.2612    1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8938   -0.0486    2.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532    4.5461   -0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9153    3.4963   -0.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0953    0.3656   -3.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9295    1.8986   -3.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093    1.9976   -3.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4017   -0.1602   -1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9189    2.5721   -0.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2592    0.5027   -1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3619    2.5691    1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4691    0.9096    1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2098    2.0830    2.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  1  0
  2  1  2  3
  2 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 34 33  1  0
 33 32  1  0
 32 31  1  0
 31 29  1  0
 29 30  1  6
 29 28  1  0
 28 27  2  0
 27 25  1  0
 25 26  2  0
 25 19  1  0
 19 20  1  0
 19 21  1  1
 21 22  1  0
 22 23  1  0
 22 24  2  0
 19 18  1  0
 18 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 13 11  1  0
 11 12  1  1
 11  9  1  0
 11  5  1  0
 31 33  1  0
 18 29  1  0
 10 44  1  0
 10 45  1  0
 10 46  1  0
  9 43  1  6
  5 42  1  1
  3 41  1  1
  1 39  1  0
  1 40  1  0
 34 66  1  6
 37 67  1  0
 37 68  1  0
 37 69  1  0
 33 65  1  6
 31 64  1  1
 30 61  1  0
 30 62  1  0
 30 63  1  0
 28 60  1  0
 27 59  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
 18 52  1  1
 13 48  1  6
 16 49  1  0
 16 50  1  0
 16 51  1  0
 12 47  1  0
M  END


  Mrv1533004241501272D          

 38 41  0  0  0  0            999 V2000
    2.9732   -0.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8580    0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1814    1.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4253    0.8328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3587    1.9687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1797    2.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6694    2.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3393    3.4690    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.4893    2.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9790    3.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8194    1.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3091    2.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1290    2.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8052    1.7328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6187    3.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6393    1.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4591    1.6806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9694    1.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4797    0.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2995    0.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8099   -0.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3202   -1.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5003   -0.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0106   -1.6392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1702   -0.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4860    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829   -0.6756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5346   -1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2735   -1.8659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473   -1.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6599    0.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3297    1.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0708    0.5718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0202    0.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5694   -0.0619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6472    1.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5099    1.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7592    0.5065    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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 25 31  1  0  0  0  0
 19 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  2  0  0  0  0
 34 36  1  0  0  0  0
 32 37  1  0  0  0  0
  2 37  1  0  0  0  0
  6 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281530

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(=O)OC2C(Cl)C(=C)C(OC(C)=O)C3OC3C3(C)C=CC(=O)C(C)(OC(C)=O)C3C(OC(C)=O)C12O

> <INCHI_IDENTIFIER>
InChI=1S/C26H31ClO11/c1-10-16(27)20-26(33,11(2)23(32)37-20)22(35-13(4)29)19-24(6,21-18(36-21)17(10)34-12(3)28)9-8-15(31)25(19,7)38-14(5)30/h8-9,11,16-22,33H,1H2,2-7H3

> <INCHI_KEY>
XNZCQTSKFNVTNR-UHFFFAOYSA-N

> <FORMULA>
C26H31ClO11

> <MOLECULAR_WEIGHT>
554.97

> <EXACT_MASS>
554.1554895

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.65342935882621

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-5-yl acetate

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
1.190033973666667

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.367008914371134

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9504703008540654

> <JCHEM_POLAR_SURFACE_AREA>
155.03

> <JCHEM_REFRACTIVITY>
127.5084

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       5.550  -0.141   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.822   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.072   2.171   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.661   1.555   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.403   3.675   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.936   3.825   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.850   5.064   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       6.233   6.476   0.000  0.00  0.00          Cl+0
HETATM    9  C   UNK     0       8.380   4.892   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.294   6.132   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.996   3.481   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.910   4.720   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.441   4.548   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.703   3.235   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.355   5.788   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.527   3.309   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.057   3.137   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.143   1.898   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.229   0.658   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.759   0.486   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.845  -0.753   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.931  -1.992   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.401  -1.820   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.486  -3.060   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.784  -0.409   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.507   0.674   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.501  -1.261   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.598  -2.798   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.977  -3.483   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.315  -3.650   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.698   0.830   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.082   2.242   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.599   1.067   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.638   1.174   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.796  -0.116   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.941   2.548   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.552   2.414   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       7.017   0.946   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   37                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17   18                                                  
CONECT   17   16   18                                                       
CONECT   18   17   16   19                                                  
CONECT   19   18   20   21   31                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   31                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   25   19   32                                                  
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   32    2    6   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
13,15-Bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0,.0,]octadec-17-en-5-yl acetic acid	Generator
13,15-Bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-5-yl acetic acid	Generator

Chemical Formula

C₂₆H₃₁ClO₁₁

Average Mass

554.9700 Da

Monoisotopic Mass

554.15549 Da

IUPAC Name

13,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-5-yl acetate

Traditional Name

13,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-5-yl acetate

CAS Registry Number

Not Available

SMILES

CC1C(=O)OC2C(Cl)C(=C)C(OC(C)=O)C3OC3C3(C)C=CC(=O)C(C)(OC(C)=O)C3C(OC(C)=O)C12O

InChI Identifier

InChI=1S/C26H31ClO11/c1-10-16(27)20-26(33,11(2)23(32)37-20)22(35-13(4)29)19-24(6,21-18(36-21)17(10)34-12(3)28)9-8-15(31)25(19,7)38-14(5)30/h8-9,11,16-22,33H,1H2,2-7H3

InChI Key

XNZCQTSKFNVTNR-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
Erythropodium caribaeorum	LOTUS Database	35616633

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
Cyclohexenone
Alpha-acyloxy ketone
Gamma butyrolactone
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alkyl chloride
Alcohol
Organic oxygen compound
Alkyl halide
Organohalogen compound
Organochloride
Organooxygen compound
Carbonyl group
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	2.19	ALOGPS
logP	1.19	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	155.03 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	127.51 m³·mol⁻¹	ChemAxon
Polarizability	52.65 Å³	ChemAxon
Number of Rings	4	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

73837561

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-13-yl acetate (NP0281530)

MOL for NP0281530 (5,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-13-yl acetate)

3D MOL for NP0281530 (5,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-13-yl acetate)

3D SDF for NP0281530 (5,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-13-yl acetate)

3D-SDF for NP0281530 (5,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-13-yl acetate)

PDB for NP0281530 (5,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-13-yl acetate)

3D PDB for NP0281530 (5,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-13-yl acetate)

SMILES for NP0281530 (5,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-13-yl acetate)

INCHI for NP0281530 (5,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-13-yl acetate)

Structure for NP0281530 (5,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-13-yl acetate)

3D Structure for NP0281530 (5,15-bis(acetyloxy)-7-chloro-12-hydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-3,9-dioxatetracyclo[12.4.0.0²,⁴.0⁸,¹²]octadec-17-en-13-yl acetate)