NP-MRD: Showing NP-Card for 2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid (NP0301431)

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Record Information

Version

2.0

Created at

2022-09-10 14:23:21 UTC

Updated at

2022-09-10 14:23:21 UTC

NP-MRD ID

NP0301431

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid

Description

2-[(3,4-Dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid is found in Actaea racemosa and Actaea simplex. 2-[(3,4-Dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121513192D          

 33 34  0  0  0  0            999 V2000
    0.6158    1.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4396    1.0690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8133    0.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371    0.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0108   -0.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5607   -1.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9344   -1.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4842   -2.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4077   -3.9914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6817   -3.3441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0554   -4.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6052   -4.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9789   -5.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814   -4.7269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792   -4.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8350   -4.9476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7030   -4.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0767   -4.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9005   -4.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2742   -5.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8240   -6.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1977   -7.1101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0002   -6.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5501   -7.0218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6265   -5.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9233   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2320   -2.8499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6589   -2.9263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7369   -1.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3632   -0.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394   -0.3138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1657    0.4218    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  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
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  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
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 19 26  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  2  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 55 56  0  0  0  0  0  0  0  0999 V2000
   -7.4124    1.2529   -3.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1804   -0.0687   -2.6512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0296   -0.3969   -1.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1196    0.5614   -1.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9553    0.2424   -0.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6735   -1.0444   -0.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4895   -1.4416    0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584   -0.6163    0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3595   -1.0408    1.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1867   -2.2444    1.6621 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -0.1418    1.7193 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813   -0.4658    2.4258 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8069    0.2496    3.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7551    0.1198    4.5494 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7752    1.0821    4.0661 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0490   -0.1231    1.6581 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1218   -0.4934    2.4681 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1023    1.3531    1.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3527    1.6687    0.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5116    1.9769    1.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6468    2.2725    0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6839    2.2762   -0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8144    2.5704   -1.5009 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5269    1.9688   -1.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4897    1.9529   -2.8677 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3605    1.6650   -0.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1002   -0.8973    0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2330   -0.8290   -0.4894 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1555   -1.7897    0.1627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6257   -2.0029   -0.8607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7701   -1.6921   -1.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6847   -2.6762   -1.8829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4438   -4.0152   -1.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3689    1.3515   -3.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4155    1.9618   -2.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6280    1.6386   -3.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3077    1.5760   -1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2536    1.0240   -0.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3677   -2.4805    0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260    0.4318    0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8574   -1.5532    2.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1706    1.0023    3.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9911   -0.3623    2.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0728    1.9154    2.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2640    1.6700    0.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4886    1.9757    2.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5726    2.5185    1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7935    2.5605   -2.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6459    1.7287   -3.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4467    1.4287   -1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1161   -1.5528    0.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4227   -3.0264   -0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2717   -4.6792   -1.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4929   -4.3181   -1.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3253   -4.0441   -0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
 12 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
 16 27  1  0
 27 29  1  0
 27 28  2  0
  6 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 31  3  1  0
 26 19  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  5 38  1  0
  7 39  1  0
  8 40  1  0
 12 41  1  1
 15 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 20 46  1  0
 21 47  1  0
 23 48  1  0
 25 49  1  0
 26 50  1  0
 29 51  1  0
 30 52  1  0
 33 53  1  0
 33 54  1  0
 33 55  1  0
M  END


  Mrv0541 04121513192D          

 33 34  0  0  0  0            999 V2000
    0.6158    1.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4396    1.0690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8133    0.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371    0.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0108   -0.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5607   -1.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9344   -1.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4842   -2.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4077   -3.9914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6817   -3.3441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0554   -4.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6052   -4.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9789   -5.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814   -4.7269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792   -4.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8350   -4.9476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7030   -4.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0767   -4.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9005   -4.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2742   -5.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8240   -6.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1977   -7.1101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0002   -6.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5501   -7.0218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6265   -5.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9233   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2320   -2.8499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6589   -2.9263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7369   -1.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3632   -0.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394   -0.3138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1657    0.4218    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  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
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  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
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 19 26  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  2  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0301431

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=CC(=O)OC(C(O)=O)C(O)(CC2=CC=C(O)C(O)=C2)C(O)=O)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O11/c1-31-16-7-4-12(10-17(16)32-2)5-8-18(25)33-19(20(26)27)22(30,21(28)29)11-13-3-6-14(23)15(24)9-13/h3-10,19,23-24,30H,11H2,1-2H3,(H,26,27)(H,28,29)

> <INCHI_KEY>
YMPYAGUNPNITIL-UHFFFAOYSA-N

> <FORMULA>
C22H22O11

> <MOLECULAR_WEIGHT>
462.407

> <EXACT_MASS>
462.116211528

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.320267569349696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
2.371709908333333

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.413956735322977

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9818970095094683

> <JCHEM_PKA_STRONGEST_BASIC>
-4.510960343020998

> <JCHEM_POLAR_SURFACE_AREA>
180.04999999999998

> <JCHEM_REFRACTIVITY>
112.0016

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       1.150   2.078   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.687   1.995   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.385   0.622   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.923   0.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.620  -0.833   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.780  -2.123   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.477  -3.496   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.637  -4.787   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.494  -7.451   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.873  -6.242   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.570  -7.615   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.730  -8.906   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.427 -10.279   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.192  -8.824   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.108  -7.698   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.025  -9.236   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.646  -7.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.343  -9.153   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.881  -9.236   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.578 -10.609   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.738 -11.899   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.436 -13.272   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.200 -11.817   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.360 -13.107   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.503 -10.444   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.190  -6.160   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.900  -5.320   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      10.563  -5.462   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.242  -2.041   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.545  -0.668   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.007  -0.586   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.309   0.787   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12   17   18   27                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19                                                       
CONECT   27   16   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    6   31                                                       
CONECT   31   30    3   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Value	Source
2-[(3,4-Dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioate	Generator

Chemical Formula

C₂₂H₂₂O₁₁

Average Mass

462.4070 Da

Monoisotopic Mass

462.11621 Da

IUPAC Name

2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid

Traditional Name

2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=CC(=O)OC(C(O)=O)C(O)(CC2=CC=C(O)C(O)=C2)C(O)=O)C=C1OC

InChI Identifier

InChI=1S/C22H22O11/c1-31-16-7-4-12(10-17(16)32-2)5-8-18(25)33-19(20(26)27)22(30,21(28)29)11-13-3-6-14(23)15(24)9-13/h3-10,19,23-24,30H,11H2,1-2H3,(H,26,27)(H,28,29)

InChI Key

YMPYAGUNPNITIL-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
Actaea racemosa	LOTUS Database	35616633
Actaea simplex	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Cinnamic acid ester
Coumaric acid or derivatives
3-phenylpropanoic-acid
Dimethoxybenzene
O-dimethoxybenzene
Tricarboxylic acid or derivatives
Catechol
Methoxybenzene
Styrene
Phenol ether
Phenoxy compound
Anisole
Sugar acid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Alpha-hydroxy acid
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Hydroxy acid
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	2.58	ALOGPS
logP	2.37	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	2.98	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.05 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	112 m³·mol⁻¹	ChemAxon
Polarizability	44.32 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

73043779

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid (NP0301431)

MOL for NP0301431 (2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid)

3D MOL for NP0301431 (2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid)

3D SDF for NP0301431 (2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid)

3D-SDF for NP0301431 (2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid)

PDB for NP0301431 (2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid)

3D PDB for NP0301431 (2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid)

SMILES for NP0301431 (2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid)

INCHI for NP0301431 (2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid)

Structure for NP0301431 (2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid)

3D Structure for NP0301431 (2-[(3,4-dihydroxyphenyl)methyl]-3-{[3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-2-hydroxybutanedioic acid)