NP-MRD: Showing NP-Card for (3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate (NP0225137)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 03:46:22 UTC

Updated at

2022-09-06 03:46:22 UTC

NP-MRD ID

NP0225137

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate

Description

(3,4,5-Trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]Dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid (3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]Dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161507542D          

 36 40  0  0  0  0            999 V2000
    3.0815    1.9191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3547    1.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1467    0.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6415   -0.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0118   -0.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0727   -1.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3103   -0.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5182   -0.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0776    0.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186    0.9831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107    1.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1070    2.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111    2.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810    2.3550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8768    2.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    2.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2647    3.2656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0568    3.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2531    2.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6526    3.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4447    3.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0406    3.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8327    3.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4285    4.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2322    5.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8281    5.6572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4402    5.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8443    4.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    3.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2764    4.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1115    3.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078    4.7590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7074    3.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995    3.6178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066    0.6432    0.0000 C   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  1  0  0  0  0
  4  5  1  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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 19  1  4  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 16 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 14 34  1  0  0  0  0
 34 35  1  0  0  0  0
 12 36  1  0  0  0  0
  3 36  1  0  0  0  0
  8 36  1  0  0  0  0
M  END

     RDKit          3D

 64 68  0  0  0  0  0  0  0  0999 V2000
    3.5609   -1.6889    1.0619 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5945   -0.4444    1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6687    0.2051    0.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5363   -0.4514   -0.3528 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5984    0.1876   -1.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7964    1.5337   -1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8314    2.0958   -1.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6974    1.2947   -2.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7159    1.8513   -3.3734 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5129   -0.0890   -2.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4953   -0.6004   -1.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6971    0.2046    1.8664 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6295   -0.0653    2.6583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4294   -0.7368    2.0916 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0611   -0.1014    0.9532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892   -0.5601    0.7762 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9798    0.1114   -0.2944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9758    1.0087    0.0790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5106    2.3574   -0.1754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1950    3.2581   -0.9510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4984    3.1509   -1.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1333    1.9886   -0.4797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3722    1.5271   -1.2147 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4328    2.2802   -0.7659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4564    0.0827   -0.7752 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7907   -0.8834   -1.4913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0604   -0.3414   -0.4113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8433   -1.2213    0.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1037   -1.5681    1.3066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1895    0.8051   -0.7433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4865   -2.0431    0.6930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1205   -2.6244    1.8044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0691   -2.6294    0.6817 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7273   -2.0050   -0.2804 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5269   -2.2034    2.0436 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3672   -2.7858    2.9994 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7000    1.2808    0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4560   -1.5258   -0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1364    2.2032   -0.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9734    3.1611   -1.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6399    2.1291   -4.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2107   -0.6902   -3.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3689   -1.6801   -1.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9480   -0.6444    3.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2891    0.9119    3.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4255   -0.4950    2.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9074   -0.2082    1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1426    0.9879    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333    4.0839   -1.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0564    3.8229   -1.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2884    2.1617    0.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1561    1.6346   -2.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3226    3.1919   -1.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2991   -0.2029   -0.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4203   -2.1920    0.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2335   -0.7483    1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3568   -0.9888    2.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9403    0.8129   -1.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630   -2.4024   -0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6973   -3.3685    1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0817   -3.7142    0.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6744   -2.4387   -1.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4869   -2.6847    2.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578   -3.2977    3.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 27 28  1  1
 27 26  1  0
 26 25  1  0
 25 23  1  0
 23 24  1  0
 23 22  1  0
 22 21  1  0
 21 20  2  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 14 35  1  0
 35 36  1  0
 35 33  1  0
 33 34  1  0
 33 31  1  0
 31 32  1  0
 18 30  1  0
 25 27  1  0
 30 22  1  0
 30 27  1  0
 31 16  1  0
 11  5  1  0
 29 57  1  0
 28 55  1  0
 28 56  1  0
 25 54  1  1
 23 52  1  6
 24 53  1  0
 22 51  1  1
 21 50  1  0
 20 49  1  0
 18 48  1  1
 16 47  1  1
 14 46  1  1
 13 44  1  0
 13 45  1  0
  3 37  1  0
  4 38  1  0
  6 39  1  0
  7 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 35 63  1  1
 36 64  1  0
 33 61  1  6
 34 62  1  0
 31 59  1  6
 32 60  1  0
 30 58  1  6
M  END


  Mrv1533004161507542D          

 36 40  0  0  0  0            999 V2000
    3.0815    1.9191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3547    1.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1467    0.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6415   -0.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0118   -0.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0727   -1.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3103   -0.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5182   -0.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0776    0.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186    0.9831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107    1.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1070    2.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111    2.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810    2.3550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8768    2.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    2.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2647    3.2656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0568    3.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2531    2.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6526    3.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4447    3.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0406    3.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8327    3.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4285    4.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2322    5.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8281    5.6572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4402    5.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8443    4.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    3.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2764    4.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1115    3.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078    4.7590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7074    3.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995    3.6178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066    0.6432    0.0000 C   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  1  0  0  0  0
  4  5  1  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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 19  1  4  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 16 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 14 34  1  0  0  0  0
 34 35  1  0  0  0  0
 12 36  1  0  0  0  0
  3 36  1  0  0  0  0
  8 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225137

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC12OC1C(O)C1C=COC(OC3OC(COC(=O)C=CC4=CC=C(O)C=C4)C(O)C(O)C3O)C21

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O12/c25-10-24-16-13(17(28)21(24)36-24)7-8-32-22(16)35-23-20(31)19(30)18(29)14(34-23)9-33-15(27)6-3-11-1-4-12(26)5-2-11/h1-8,13-14,16-23,25-26,28-31H,9-10H2

> <INCHI_KEY>
AKYYFSOMEOHPPO-UHFFFAOYSA-N

> <FORMULA>
C24H28O12

> <MOLECULAR_WEIGHT>
508.476

> <EXACT_MASS>
508.158076342

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.82853229117405

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
-0.09

> <JCHEM_LOGP>
-0.7014782133333333

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.193763714232235

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.397947745266052

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1218025089548433

> <JCHEM_POLAR_SURFACE_AREA>
187.9

> <JCHEM_REFRACTIVITY>
118.74010000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate

> <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  O   UNK     0       5.752   3.582   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.395   2.854   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.348   1.314   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.874   1.107   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.931  -0.111   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.755  -1.106   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.869  -2.642   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.446  -0.295   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.967  -0.726   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.145   0.339   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.221   1.835   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.700   2.266   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.066   3.762   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.954   4.827   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.524   4.396   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.637   5.461   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.115   5.031   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.227   6.096   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.706   5.665   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.072   4.169   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.818   6.730   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.297   6.300   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.409   7.365   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.888   6.934   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -12.000   7.999   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -11.634   9.495   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -12.746  10.560   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -10.155   9.926   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.043   8.861   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.270   6.957   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.383   8.022   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.208   7.388   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.575   8.883   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.320   6.323   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.799   6.753   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.812   1.201   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   36                                             
CONECT    4    3    5                                                       
CONECT    5    4    3    6                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   36                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   36                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   34                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   30                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23                                                       
CONECT   30   16   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   14   35                                                  
CONECT   35   34                                                            
CONECT   36   12    3    8                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
(3,4,5-Trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0,]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoic acid	Generator
(3,4,5-Trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₄H₂₈O₁₂

Average Mass

508.4760 Da

Monoisotopic Mass

508.15808 Da

IUPAC Name

(3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

(3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OCC12OC1C(O)C1C=COC(OC3OC(COC(=O)C=CC4=CC=C(O)C=C4)C(O)C(O)C3O)C21

InChI Identifier

InChI=1S/C24H28O12/c25-10-24-16-13(17(28)21(24)36-24)7-8-32-22(16)35-23-20(31)19(30)18(29)14(34-23)9-33-15(27)6-3-11-1-4-12(26)5-2-11/h1-8,13-14,16-23,25-26,28-31H,9-10H2

InChI Key

AKYYFSOMEOHPPO-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Monosaccharide
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Acetal
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Carbonyl group
Primary alcohol
Organic oxide
Hydrocarbon derivative
Alcohol
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	-0.09	ALOGPS
logP	-0.7	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	187.9 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	118.74 m³·mol⁻¹	ChemAxon
Polarizability	49.83 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

74155558

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate (NP0225137)

MOL for NP0225137 ((3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0225137 ((3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0225137 ((3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0225137 ((3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0225137 ((3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0225137 ((3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0225137 ((3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0225137 ((3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0225137 ((3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0225137 ((3,4,5-trihydroxy-6-{[5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl)methyl 3-(4-hydroxyphenyl)prop-2-enoate)