NP-MRD: Showing NP-Card for clinopodic acid C (NP0034633)

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Record Information

Version

2.0

Created at

2021-06-20 18:18:26 UTC

Updated at

2021-06-30 00:05:09 UTC

NP-MRD ID

NP0034633

Secondary Accession Numbers

None

Natural Product Identification

Common Name

clinopodic acid C

Provided By

JEOL Database JEOL Logo

Description

Clinopodic acid C, also known as clinopodate C, belongs to the class of organic compounds known as phenylbenzo-1,4-dioxanes. These are benzo-1,3-dioxanes having a phenyl group attached to the 1,4-dioxane moiety. clinopodic acid C is found in Clinopodium chinense, Clinopodium chinense var. parviflorum, Lycopus lucidus and Salvia flava . clinopodic acid C was first documented in 2009 (PMID: 19711986). Based on a literature review very few articles have been published on Clinopodic acid C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120183D          

 61 64  0  0  0  0            999 V2000
   -1.6240    1.0889   -4.7004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9920    0.4081   -3.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3985    0.8855   -2.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5005    2.1794   -2.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0358    2.7518   -1.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273    3.8435   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1478    4.4297    0.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0045    3.9350    1.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6953    2.8761    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114    2.2819   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8503    2.3521    1.2223 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4397    3.2237    2.1929 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5538    2.5142    2.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8774    1.3404    2.8509 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2419    3.3349    3.7667 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    3.7961    3.1714 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7079    2.8726    4.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0907    3.4591    5.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353    2.6798    6.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6304    1.4775    4.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3970    4.5424    2.4557 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2440   -1.5218   -5.2211 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1655   -3.0442   -5.0604 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.4261   -4.3387   -3.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0585   -4.4760   -2.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9365   -4.9166   -1.2574 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4143   -4.2935   -0.4868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8221   -3.7066   -2.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4119   -1.1171   -6.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6732   -0.5573   -6.4287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9940   -1.4525   -7.6048 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3789   -1.0948   -8.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0  0  0  0
 36 29  1  0  0  0  0
  2 26  1  0  0  0  0
 29 30  2  0  0  0  0
  5  6  2  0  0  0  0
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  8  9  1  0  0  0  0
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  9 11  1  0  0  0  0
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 16 25  1  0  0  0  0
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  8 25  1  0  0  0  0
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M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
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   -0.9920    0.4081   -3.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202120183D          

 61 64  0  0  0  0            999 V2000
   -1.6240    1.0889   -4.7004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9920    0.4081   -3.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8774    1.3404    2.8509 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4143   -4.2935   -0.4868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8221   -3.7066   -2.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4119   -1.1171   -6.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6732   -0.5573   -6.4287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9940   -1.4525   -7.6048 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0920    0.1470   -2.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0281    2.8727   -2.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7746    1.4629   -0.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140    4.0381    1.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9333    4.5423    3.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0698    0.9833    3.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2815   -1.1989   -5.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3339   -3.5516   -6.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2267   -4.6187   -0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8219   -3.4617   -2.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789   -1.0948   -8.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0  0  0  0
 36 29  1  0  0  0  0
  2 26  1  0  0  0  0
 29 30  2  0  0  0  0
  5  6  2  0  0  0  0
 30 31  1  0  0  0  0
 26 27  1  0  0  0  0
 31 32  2  0  0  0  0
  8  9  1  0  0  0  0
 32 34  1  0  0  0  0
 34 36  2  0  0  0  0
 27 28  1  0  0  0  0
 32 33  1  0  0  0  0
 28 29  1  0  0  0  0
  9 11  1  0  0  0  0
  9 10  2  0  0  0  0
 16 25  1  0  0  0  0
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  5  4  1  0  0  0  0
 13 14  2  0  0  0  0
  2  1  2  0  0  0  0
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  6  7  1  0  0  0  0
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 24 22  1  0  0  0  0
  4  3  2  0  0  0  0
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  3  2  1  0  0  0  0
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 19 49  1  0  0  0  0
 18 48  1  0  0  0  0
 21 50  1  0  0  0  0
 23 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034633

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]([H])(OC(=O)C(\[H])=C(/[H])C1=C([H])C([H])=C2O[C@@]([H])(C3=C([H])C(O[H])=C(O[H])C([H])=C3[H])[C@]([H])(OC2=C1[H])C(=O)O[H])C([H])([H])C1=C([H])C([H])=C(O[H])C(O[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H22O12/c28-16-5-1-14(9-18(16)30)11-22(26(33)34)37-23(32)8-3-13-2-7-20-21(10-13)39-25(27(35)36)24(38-20)15-4-6-17(29)19(31)12-15/h1-10,12,22,24-25,28-31H,11H2,(H,33,34)(H,35,36)/b8-3+/t22-,24+,25+/m1/s1

> <INCHI_KEY>
KPKHMGUZUPELJC-RXYMDKBQSA-N

> <FORMULA>
C27H22O12

> <MOLECULAR_WEIGHT>
538.461

> <EXACT_MASS>
538.111126148

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
52.306485419722506

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-7-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
3.991438589666666

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.3405831469974925

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7194644939246646

> <JCHEM_PKA_STRONGEST_BASIC>
-6.2891616673888295

> <JCHEM_POLAR_SURFACE_AREA>
200.28

> <JCHEM_REFRACTIVITY>
132.02020000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
clinopodic acid C

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
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   -0.3789   -1.0948   -8.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
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  2 26  1  0
 29 30  2  0
  5  6  2  0
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 26 27  1  0
 31 32  2  0
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 32 34  1  0
 34 36  2  0
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  9 10  2  0
 16 25  1  0
 34 35  1  0
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 12 16  1  0
 10  5  1  0
 16 17  1  0
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 12 13  1  0
  5  4  1  0
 13 14  2  0
  2  1  2  0
 13 15  1  0
  6  7  1  0
 17 24  2  0
 27 37  1  0
 24 22  1  0
  4  3  2  0
 22 20  2  0
 37 38  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 37 39  1  0
 20 21  1  0
  3  2  1  0
 22 23  1  0
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  6 42  1  0
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 27 53  1  6
 28 54  1  0
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 35 59  1  0
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 16 47  1  1
 12 45  1  6
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 24 52  1  0
 19 49  1  0
 18 48  1  0
 21 50  1  0
 23 51  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0      -1.624   1.089  -4.700  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.992   0.408  -3.910  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.399   0.886  -2.646  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.500   2.179  -2.306  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.036   2.752  -1.063  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.627   3.844  -0.485  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.148   4.430   0.690  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.004   3.935   1.293  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.695   2.876   0.705  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.211   2.282  -0.462  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.850   2.352   1.222  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.440   3.224   2.193  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.554   2.514   2.944  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.877   1.340   2.851  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.242   3.335   3.767  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.403   3.796   3.171  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.708   2.873   4.170  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.091   3.459   5.297  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.435   2.680   6.253  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.387   1.307   6.084  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.251   0.540   7.016  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.976   0.708   4.976  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.885  -0.653   4.868  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.630   1.478   4.017  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.397   4.542   2.456  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.722  -0.915  -4.027  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.244  -1.522  -5.221  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.165  -3.044  -5.060  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.174  -3.564  -4.060  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.482  -3.880  -4.466  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.426  -4.339  -3.541  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.059  -4.476  -2.209  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.936  -4.917  -1.257  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.766  -4.161  -1.800  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.414  -4.293  -0.487  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.822  -3.707  -2.710  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.412  -1.117  -6.433  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.673  -0.557  -6.429  0.00  0.00           O+0
HETATM   39  O   UNK     0      -0.994  -1.452  -7.605  0.00  0.00           O+0
HETATM   40  H   UNK     0       0.092   0.147  -2.025  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.028   2.873  -2.960  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.535   4.240  -0.935  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.683   5.262   1.140  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.775   1.463  -0.902  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.914   4.038   1.627  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.924   2.753   4.168  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.933   4.542   3.780  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.113   4.540   5.431  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.035   3.141   7.115  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.164  -0.373   6.677  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.334  -0.922   4.047  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.070   0.983   3.156  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.281  -1.199  -5.378  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.334  -3.552  -6.019  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.158  -3.340  -4.737  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.774  -3.770  -5.509  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.429  -4.577  -3.879  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.790  -5.088  -1.691  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.227  -4.619  -0.050  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.822  -3.462  -2.363  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.379  -1.095  -8.281  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   26    1    3                                                  
CONECT    3    4    2   40                                                  
CONECT    4    5    3   41                                                  
CONECT    5    6   10    4                                                  
CONECT    6    5    7   42                                                  
CONECT    7    8    6   43                                                  
CONECT    8    7    9   25                                                  
CONECT    9    8   11   10                                                  
CONECT   10    9    5   44                                                  
CONECT   11    9   12                                                       
CONECT   12   11   16   13   45                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   46                                                       
CONECT   16   25   12   17   47                                             
CONECT   17   16   24   18                                                  
CONECT   18   19   17   48                                                  
CONECT   19   20   18   49                                                  
CONECT   20   22   19   21                                                  
CONECT   21   20   50                                                       
CONECT   22   24   20   23                                                  
CONECT   23   22   51                                                       
CONECT   24   17   22   52                                                  
CONECT   25   16    8                                                       
CONECT   26    2   27                                                       
CONECT   27   26   28   37   53                                             
CONECT   28   27   29   54   55                                             
CONECT   29   36   30   28                                                  
CONECT   30   29   31   56                                                  
CONECT   31   30   32   57                                                  
CONECT   32   31   34   33                                                  
CONECT   33   32   58                                                       
CONECT   34   32   36   35                                                  
CONECT   35   34   59                                                       
CONECT   36   29   34   60                                                  
CONECT   37   27   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   61                                                       
CONECT   40    3                                                            
CONECT   41    4                                                            
CONECT   42    6                                                            
CONECT   43    7                                                            
CONECT   44   10                                                            
CONECT   45   12                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   21                                                            
CONECT   51   23                                                            
CONECT   52   24                                                            
CONECT   53   27                                                            
CONECT   54   28                                                            
CONECT   55   28                                                            
CONECT   56   30                                                            
CONECT   57   31                                                            
CONECT   58   33                                                            
CONECT   59   35                                                            
CONECT   60   36                                                            
CONECT   61   39                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  128    0
END

RDKit          3D

61 64  0  0  0  0  0  0  0  0999 V2000
   -1.6240    1.0889   -4.7004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9920    0.4081   -3.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3985    0.8855   -2.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5005    2.1794   -2.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0358    2.7518   -1.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273    3.8435   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1478    4.4297    0.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0045    3.9350    1.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6953    2.8761    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114    2.2819   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8503    2.3521    1.2223 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4397    3.2237    2.1929 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5538    2.5142    2.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8774    1.3404    2.8509 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2419    3.3349    3.7667 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    3.7961    3.1714 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7079    2.8726    4.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0907    3.4591    5.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353    2.6798    6.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3866    1.3072    6.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2511    0.5403    7.0160 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9755    0.7082    4.9757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854   -0.6530    4.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6304    1.4775    4.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3970    4.5424    2.4557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7219   -0.9147   -4.0267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2440   -1.5218   -5.2211 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1655   -3.0442   -5.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1740   -3.5643   -4.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4821   -3.8803   -4.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4261   -4.3387   -3.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0585   -4.4760   -2.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9365   -4.9166   -1.2574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659   -4.1607   -1.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4143   -4.2935   -0.4868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8221   -3.7066   -2.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4119   -1.1171   -6.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6732   -0.5573   -6.4287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9940   -1.4525   -7.6048 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0920    0.1470   -2.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0281    2.8727   -2.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5353    4.2401   -0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6831    5.2618    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7746    1.4629   -0.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140    4.0381    1.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9240    2.7533    4.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9333    4.5423    3.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1134    4.5397    5.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0352    3.1409    7.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643   -0.3731    6.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3336   -0.9216    4.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698    0.9833    3.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2815   -1.1989   -5.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3339   -3.5516   -6.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1584   -3.3400   -4.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7736   -3.7698   -5.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4293   -4.5774   -3.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7901   -5.0877   -1.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2267   -4.6187   -0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8219   -3.4617   -2.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789   -1.0948   -8.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
 36 29  1  0
  2 26  1  0
 29 30  2  0
  5  6  2  0
 30 31  1  0
 26 27  1  0
 31 32  2  0
  8  9  1  0
 32 34  1  0
 34 36  2  0
 27 28  1  0
 32 33  1  0
 28 29  1  0
  9 11  1  0
  9 10  2  0
 16 25  1  0
 34 35  1  0
 12 11  1  0
 12 16  1  0
 10  5  1  0
 16 17  1  0
  8 25  1  0
 12 13  1  0
  5  4  1  0
 13 14  2  0
  2  1  2  0
 13 15  1  0
  6  7  1  0
 17 24  2  0
 27 37  1  0
 24 22  1  0
  4  3  2  0
 22 20  2  0
 37 38  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 37 39  1  0
 20 21  1  0
  3  2  1  0
 22 23  1  0
 10 44  1  0
  6 42  1  0
  7 43  1  0
  4 41  1  0
  3 40  1  0
 27 53  1  6
 28 54  1  0
 28 55  1  0
 35 59  1  0
 39 61  1  0
 36 60  1  0
 30 56  1  0
 31 57  1  0
 33 58  1  0
 16 47  1  1
 12 45  1  6
 15 46  1  0
 24 52  1  0
 19 49  1  0
 18 48  1  0
 21 50  1  0
 23 51  1  0
M  END

View in JSmol

Synonyms

Value	Source
Clinopodate C	Generator

Chemical Formula

C₂₇H₂₂O₁₂

Average Mass

538.4610 Da

Monoisotopic Mass

538.11113 Da

IUPAC Name

(2S,3S)-7-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-3-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid

Traditional Name

clinopodic acid C

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@]([H])(OC(=O)C(\[H])=C(/[H])C1=C([H])C([H])=C2O[C@@]([H])(C3=C([H])C(O[H])=C(O[H])C([H])=C3[H])[C@]([H])(OC2=C1[H])C(=O)O[H])C([H])([H])C1=C([H])C([H])=C(O[H])C(O[H])=C1[H]

InChI Identifier

InChI=1S/C27H22O12/c28-16-5-1-14(9-18(16)30)11-22(26(33)34)37-23(32)8-3-13-2-7-20-21(10-13)39-25(27(35)36)24(38-20)15-4-6-17(29)19(31)12-15/h1-10,12,22,24-25,28-31H,11H2,(H,33,34)(H,35,36)/b8-3+/t22-,24+,25+/m1/s1

InChI Key

KPKHMGUZUPELJC-RXYMDKBQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Clinopodium chinense	LOTUS Database	35616633
Clinopodium chinense var. parviflorum	JEOL database	Murata, T., et al, J. Nat. Prod. 72, 1379 (2009)
Lycopus lucidus	LOTUS Database	35616633
Salvia flava	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbenzo-1,4-dioxanes. These are benzo-1,3-dioxanes having a phenyl group attached to the 1,4-dioxane moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxanes

Sub Class

Phenylbenzodioxanes

Direct Parent

Phenylbenzo-1,4-dioxanes

Alternative Parents

Substituents

2-phenylbenzo-1,4-dioxane
Cinnamic acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
3-phenylpropanoic-acid
Benzo-1,4-dioxane
Tricarboxylic acid or derivatives
Catechol
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
Phenol
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Para-dioxin
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Ether
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	3.65	ALOGPS
logP	3.99	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	200.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	132.02 m³·mol⁻¹	ChemAxon
Polarizability	52.31 Å³	ChemAxon
Number of Rings	4	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

24660678

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44254596

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Murata T, Sasaki K, Sato K, Yoshizaki F, Yamada H, Mutoh H, Umehara K, Miyase T, Warashina T, Aoshima H, Tabata H, Matsubara K: Matrix metalloproteinase-2 inhibitors from Clinopodium chinense var. parviflorum. J Nat Prod. 2009 Aug;72(8):1379-84. doi: 10.1021/np800781t. [PubMed:19711986 ]
Murata, T., et al. (2009). Murata, T., et al, J. Nat. Prod. 72, 1379 (2009). J. Nat. Prod..

Showing NP-Card for clinopodic acid C (NP0034633)

MOL for NP0034633 (clinopodic acid C)

3D MOL for NP0034633 (clinopodic acid C)

3D SDF for NP0034633 (clinopodic acid C)

3D-SDF for NP0034633 (clinopodic acid C)

PDB for NP0034633 (clinopodic acid C)

3D PDB for NP0034633 (clinopodic acid C)

SMILES for NP0034633 (clinopodic acid C)

INCHI for NP0034633 (clinopodic acid C)

Structure for NP0034633 (clinopodic acid C)

3D Structure for NP0034633 (clinopodic acid C)