NP-MRD: Showing NP-Card for 5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2e)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2e)-3-phenylprop-2-enoate (NP0319444)

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Record Information

Version

2.0

Created at

2022-09-11 20:28:16 UTC

Updated at

2022-09-11 20:28:16 UTC

NP-MRD ID

NP0319444

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2e)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2e)-3-phenylprop-2-enoate

Description

Koelzioside belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. 5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2e)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2e)-3-phenylprop-2-enoate is found in Scrophularia deserti and Scrophularia koelzii. 5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2e)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2e)-3-phenylprop-2-enoate was first documented in 2003 (PMID: 12673026). Based on a literature review very few articles have been published on Koelzioside (PMID: 29666580).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112222282D          

 58 64  0  0  0  0            999 V2000
    6.0741    3.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3921    3.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6491    3.8399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4531    2.6586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7710    2.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8320    1.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5750    1.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500    0.9075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4070    1.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7249    0.8019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7859   -0.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4874   -0.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2795   -0.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8753   -0.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6791   -1.5964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870   -1.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6907   -2.6284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2866   -3.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0786   -2.9683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6745   -3.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4666   -3.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0624   -3.8788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4782   -4.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0741   -4.9108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6861   -4.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4899   -5.3722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0903   -4.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2982   -4.2310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2911   -1.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4684   -1.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430   -2.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162   -2.5324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6509   -1.2060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1561   -0.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460    2.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6030    2.4474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9210    1.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9819    1.1604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1780    2.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959    1.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471    2.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9291    1.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721    2.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7331    2.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0511    3.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3081    3.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280    2.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9670    3.3757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2240    3.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5420    3.2701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1631    4.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4201    4.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3591    5.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6161    6.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5551    6.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2371    7.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9801    7.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0411    6.2025    0.0000 C   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
  2  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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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  2  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  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  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
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 16 29  1  0  0  0  0
 12 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
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 11 34  1  0  0  0  0
 30 34  1  0  0  0  0
  9 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 41 46  1  0  0  0  0
 35 47  1  0  0  0  0
  5 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 53 58  1  0  0  0  0
M  END

     RDKit          3D

104110  0  0  0  0  0  0  0  0999 V2000
   -4.1358    2.9118    4.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0109    2.5438    3.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8866    1.3265    2.8256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6340    1.1287    2.0955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9489    0.1509    3.0448 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5189    0.3518    3.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4358   -1.1508    2.9756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4163   -1.5395    1.6640 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3099   -1.2264    1.0367 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4421   -0.4449   -0.4808 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5019    0.9492    0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5424    1.5957   -0.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2956    0.8284   -1.4089 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8491   -0.4241   -0.8264 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0271   -0.1503   -0.2785 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1864   -0.6618   -0.6905 C   0  0  2  0  0  0  0  0  0  0  0  0
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    8.0782    0.4051    0.1000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8216    0.7077    1.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0071    0.9947    2.4699 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2440   -0.6312   -1.5256 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5080   -3.9935   -0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1081   -5.3223   -0.5783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9280   -6.2922    0.4483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5725   -7.4789    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3965   -7.7543   -0.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6359   -6.8183   -1.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9397   -5.6180   -1.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0947   -0.3408    2.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9237   -1.0575   -1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0463   -1.6809   -1.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2068   -3.0846   -2.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9182   -3.8202    0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0319444

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2C3OC3(CO)C3C2C=COC3OC2OC(CO)C(O)C(O)C2O)C(OC(=O)\C=C\C2=CC=CC=C2)C(OC(=O)\C=C\C2=CC=CC=C2)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C41H46O17/c1-21-33(52-22(2)44)35(54-27(45)15-13-23-9-5-3-6-10-23)36(55-28(46)16-14-24-11-7-4-8-12-24)40(51-21)56-34-25-17-18-50-38(29(25)41(20-43)37(34)58-41)57-39-32(49)31(48)30(47)26(19-42)53-39/h3-18,21,25-26,29-40,42-43,47-49H,19-20H2,1-2H3/b15-13+,16-14+

> <INCHI_KEY>
NKORFEGGMJANHB-WXUKJITCSA-N

> <FORMULA>
C41H46O17

> <MOLECULAR_WEIGHT>
810.802

> <EXACT_MASS>
810.273500021

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
104

> <JCHEM_AVERAGE_POLARIZABILITY>
80.28695279691233

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2E)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
2.353177557666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.166493774543525

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.203215698428314

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847601929344

> <JCHEM_POLAR_SURFACE_AREA>
238.72999999999996

> <JCHEM_REFRACTIVITY>
196.34799999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2E)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      11.338   7.365   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.065   6.499   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.678   7.168   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.179   4.963   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.906   4.096   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.020   2.560   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.407   1.891   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.747   1.694   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.360   2.363   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.087   1.497   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.200  -0.039   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.510  -0.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.988  -0.419   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.101  -1.484   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.734  -2.980   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.256  -3.411   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.889  -4.906   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -5.971   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.480  -5.541   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.592  -6.606   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.071  -6.175   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.183  -7.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.226  -8.102   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.338  -9.167   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.747  -8.532   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.381 -10.028   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.635  -7.467   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.157  -7.898   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.143  -2.345   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.608  -2.459   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.560  -3.998   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.204  -4.727   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.082  -2.251   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.025  -1.034   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.246   3.899   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.859   4.568   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.586   3.702   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.700   2.166   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       2.199   4.371   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.926   3.505   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.461   4.174   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.734   3.308   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -3.121   3.977   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -3.235   5.513   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -1.962   6.379   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -0.575   5.710   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       7.519   4.766   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       7.405   6.301   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       6.018   6.971   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       4.745   6.104   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       5.904   8.506   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       4.517   9.176   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       4.404  10.712   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       3.017  11.381   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       2.903  12.917   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       4.176  13.783   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       5.563  13.114   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       5.677  11.578   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   47                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   35                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   34                                                  
CONECT   12   11   13   29                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27                                                            
CONECT   29   16   12   30                                                  
CONECT   30   29   31   33   34                                             
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34                                                       
CONECT   34   33   11   30                                                  
CONECT   35    9   36   47                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   41                                                       
CONECT   47   35    5   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   58                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   53                                                       
MASTER        0    0    0    0    0    0    0    0   58    0  128    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₁H₄₆O₁₇

Average Mass

810.8020 Da

Monoisotopic Mass

810.27350 Da

IUPAC Name

5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2E)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2E)-3-phenylprop-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1OC(OC2C3OC3(CO)C3C2C=COC3OC2OC(CO)C(O)C(O)C2O)C(OC(=O)\C=C\C2=CC=CC=C2)C(OC(=O)\C=C\C2=CC=CC=C2)C1OC(C)=O

InChI Identifier

InChI=1S/C41H46O17/c1-21-33(52-22(2)44)35(54-27(45)15-13-23-9-5-3-6-10-23)36(55-28(46)16-14-24-11-7-4-8-12-24)40(51-21)56-34-25-17-18-50-38(29(25)41(20-43)37(34)58-41)57-39-32(49)31(48)30(47)26(19-42)53-39/h3-18,21,25-26,29-40,42-43,47-49H,19-20H2,1-2H3/b15-13+,16-14+

InChI Key

NKORFEGGMJANHB-WXUKJITCSA-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
Scrophularia deserti	LOTUS Database	35616633
Scrophularia koelzii	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Styrene
Fatty acid ester
Monocyclic benzene moiety
Monosaccharide
Fatty acyl
Benzenoid
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Polyol
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Acetal
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Alcohol
Primary alcohol
Organooxygen compound
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	2.35	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	238.73 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	196.35 m³·mol⁻¹	ChemAxon
Polarizability	80.29 Å³	ChemAxon
Number of Rings	7	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

4746708

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5916545

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ahmed B, Al-Rehaily AJ, Al-Howiriny TA, El-Sayed KA, Ahmad MS: Scropolioside-D2 and harpagoside-B: two new iridoid glycosides from Scrophularia deserti and their antidiabetic and antiinflammatory activity. Biol Pharm Bull. 2003 Apr;26(4):462-7. doi: 10.1248/bpb.26.462. [PubMed:12673026 ]
Lewenhofer V, Schweighofer L, Ledermuller T, Eichsteininger J, Kahlig H, Zehl M, Nguyen CH, Krupitza G, Ozmen A, Krenn L: Chemical Composition of Scrophularia lucida and the Effects on Tumor Invasiveness in Vitro. Front Pharmacol. 2018 Apr 3;9:304. doi: 10.3389/fphar.2018.00304. eCollection 2018. [PubMed:29666580 ]
LOTUS database [Link]

Showing NP-Card for 5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2e)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2e)-3-phenylprop-2-enoate (NP0319444)

MOL for NP0319444 (5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2e)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0319444 (5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2e)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0319444 (5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2e)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0319444 (5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2e)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2e)-3-phenylprop-2-enoate)

PDB for NP0319444 (5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2e)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0319444 (5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2e)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2e)-3-phenylprop-2-enoate)

SMILES for NP0319444 (5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2e)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2e)-3-phenylprop-2-enoate)

INCHI for NP0319444 (5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2e)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2e)-3-phenylprop-2-enoate)

Structure for NP0319444 (5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2e)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0319444 (5-(acetyloxy)-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyl-4-{[(2e)-3-phenylprop-2-enoyl]oxy}oxan-3-yl (2e)-3-phenylprop-2-enoate)