NP-MRD: Showing NP-Card for Gaertneric acid (NP0026342)

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Record Information

Version

2.0

Created at

2021-06-19 18:14:31 UTC

Updated at

2021-06-29 23:51:49 UTC

NP-MRD ID

NP0026342

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gaertneric acid

Provided By

JEOL Database JEOL Logo

Description

Gaertneric acid is found in Morinda morindoides. Gaertneric acid was first documented in 2003 (Cimanga, K., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120143D          

 64 68  0  0  0  0            999 V2000
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   -2.9486    3.8538   -2.6396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458    4.4620   -3.7665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9087    2.9782   -2.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116    2.0643   -1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2534    0.8846   -1.2286 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306192120143D          

 64 68  0  0  0  0            999 V2000
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    0.4508    2.1676   -1.6764 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4771    3.0895   -2.4947 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1399    4.4372   -2.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2572    2.4663    1.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2752    3.0381    3.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1193   -0.4816    3.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5127    2.2230    0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049    1.7038    1.4453 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0710   -1.4441    0.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7267   -3.6498   -3.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7220   -5.7345   -2.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2826   -3.9934   -2.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1851   -3.9711   -4.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668   -1.7531   -4.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522   -0.9013   -4.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2820    1.8664   -2.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    2.8462   -3.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5251    5.2642   -0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5963    3.2996    1.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0142    2.0019    3.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0019    2.6379    4.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3287   -2.8427    2.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781   -2.6358    2.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2057   -0.4442    3.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 31  2  0  0  0  0
  5  4  2  0  0  0  0
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 20 21  1  0  0  0  0
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  7  8  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
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 24 20  1  0  0  0  0
 38 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21  4  1  0  0  0  0
  9 18  1  0  0  0  0
 18 16  1  0  0  0  0
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 14 11  1  0  0  0  0
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 27 28  1  0  0  0  0
 12 13  1  0  0  0  0
 20  7  1  0  0  0  0
  4  2  1  0  0  0  0
 27 29  1  0  0  0  0
  2  3  1  0  0  0  0
  7  6  1  0  0  0  0
  2  1  2  0  0  0  0
 29 30  1  0  0  0  0
 21 54  1  6  0  0  0
  6  5  1  0  0  0  0
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  3 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026342

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])O[C@@]([H])(O[C@@]2([H])O[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])[C@@]2([H])[C@]1([H])C([H])=C([H])[C@]21OC(=O)C(=C1[H])[C@@]([H])(O[H])C1=C([H])C([H])=C(O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O13/c26-8-15-18(29)19(30)20(31)24(36-15)37-23-16-12(14(9-35-23)21(32)33)5-6-25(16)7-13(22(34)38-25)17(28)10-1-3-11(27)4-2-10/h1-7,9,12,15-20,23-24,26-31H,8H2,(H,32,33)/t12-,15+,16-,17+,18+,19-,20+,23+,24-,25-/m1/s1

> <INCHI_KEY>
FTQHRAAKMDKGHW-PDAMXGFISA-N

> <FORMULA>
C25H26O13

> <MOLECULAR_WEIGHT>
534.47

> <EXACT_MASS>
534.137340897

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.72225598258211

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aS,7R,7aS)-4'-[(S)-hydroxy(4-hydroxyphenyl)methyl]-5'-oxo-1-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylic acid

> <ALOGPS_LOGP>
-0.30

> <JCHEM_LOGP>
-0.9518651563333319

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.46686194556706

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.046686645590163

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760207743

> <JCHEM_POLAR_SURFACE_AREA>
212.67

> <JCHEM_REFRACTIVITY>
124.10669999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,7R,7aS)-4'-[(S)-hydroxy(4-hydroxyphenyl)methyl]-5'-oxo-1-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 68  0  0  0  0  0  0  0  0999 V2000
   -4.0690    4.0278   -2.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7943   -1.6180   -1.4641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9367   -3.0169   -1.1398 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2753   -3.1902   -0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3083   -2.3257    0.7292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8769   -3.8774   -2.4071 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9477   -5.2675   -2.0911 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5882   -4.3086   -4.4034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4088   -2.0987   -3.4033 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8667   -1.8720   -4.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4771    3.0895   -2.4947 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1399    4.4372   -2.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9806    4.4088   -1.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0366    3.0504   -0.5502 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4227    3.0144    0.7909 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0611    2.0531    3.0870 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2752    3.0381    3.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8888   -1.7810    2.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4910   -1.7220    3.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1193   -0.4816    3.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5127    2.2230    0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049    1.7038    1.4453 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3891    2.6559   -0.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3273    4.9888   -4.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3285    1.9792   -0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3902    0.3650   -0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -1.6186   -1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1851   -3.9711   -4.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0142    2.0019    3.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0019    2.6379    4.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6474    1.5125    2.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418   -0.6749    2.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3287   -2.8427    2.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781   -2.6358    2.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2057   -0.4442    3.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 31  2  0
  5  4  2  0
 31 32  1  0
 20 21  1  0
 32 34  2  0
 26 25  2  0
 34 35  1  0
 35 29  2  0
 32 33  1  0
 24 38  1  1
  7  8  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  1  0
 38 36  1  0
 36 37  2  0
 36 26  1  0
 26 27  1  0
 21  4  1  0
  9 18  1  0
 18 16  1  0
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 14 15  1  0
 16 17  1  0
 18 19  1  0
 27 28  1  0
 12 13  1  0
 20  7  1  0
  4  2  1  0
 27 29  1  0
  2  3  1  0
  7  6  1  0
  2  1  2  0
 29 30  1  0
 21 54  1  6
  6  5  1  0
 20 53  1  6
 24 25  1  0
 11 12  1  0
  9  8  1  0
 25 57  1  0
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 27 58  1  1
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  9 42  1  1
 14 47  1  6
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 18 51  1  6
 19 52  1  0
 12 44  1  0
 12 45  1  0
 11 43  1  1
 13 46  1  0
  3 39  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0      -4.069   4.028  -2.196  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.949   3.854  -2.640  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.546   4.462  -3.767  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.909   2.978  -2.074  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.312   2.064  -1.179  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.515   1.119  -0.588  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.253   0.885  -1.229  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.408   0.056  -2.392  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.535  -1.335  -2.071  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.794  -1.618  -1.464  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.937  -3.017  -1.140  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.275  -3.190  -0.414  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.308  -2.326   0.729  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.877  -3.877  -2.407  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.948  -5.268  -2.091  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.574  -3.596  -3.157  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.588  -4.309  -4.403  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.409  -2.099  -3.403  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.867  -1.872  -4.024  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.451   2.168  -1.676  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.477   3.090  -2.495  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.140   4.437  -2.212  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.981   4.409  -1.169  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.037   3.050  -0.550  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.423   3.014   0.791  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.257   2.466   1.675  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.061   2.053   3.087  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.275   3.038   3.760  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.364   0.703   3.127  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.036   0.612   3.019  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.661  -0.627   2.891  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.889  -1.781   2.856  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.465  -2.997   2.636  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.491  -1.722   3.004  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.119  -0.482   3.135  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.513   2.223   0.969  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.505   1.704   1.445  0.00  0.00           O+0
HETATM   38  O   UNK     0       2.389   2.656  -0.317  0.00  0.00           O+0
HETATM   39  H   UNK     0      -3.327   4.989  -4.037  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.329   1.979  -0.810  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.390   0.365  -0.509  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.288  -1.619  -1.401  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.136  -3.289  -0.440  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.421  -4.218  -0.069  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.115  -2.907  -1.057  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.071  -1.444   0.368  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.727  -3.650  -3.063  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.722  -5.734  -2.922  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.283  -3.993  -2.598  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.185  -3.971  -4.900  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.167  -1.753  -4.118  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.952  -0.901  -4.099  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.282   1.866  -2.336  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.383   2.846  -3.560  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.078   5.322  -2.797  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.525   5.264  -0.792  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.596   3.300   1.014  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.014   2.002   3.625  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.002   2.638   4.603  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.647   1.513   2.992  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.742  -0.675   2.798  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.329  -2.843   2.192  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.078  -2.636   2.985  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.206  -0.444   3.203  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    4    3    1                                                  
CONECT    3    2   39                                                       
CONECT    4    5   21    2                                                  
CONECT    5    4    6   40                                                  
CONECT    6    7    5                                                       
CONECT    7    8   20    6   41                                             
CONECT    8    7    9                                                       
CONECT    9   18   10    8   42                                             
CONECT   10   11    9                                                       
CONECT   11   14   10   12   43                                             
CONECT   12   13   11   44   45                                             
CONECT   13   12   46                                                       
CONECT   14   16   11   15   47                                             
CONECT   15   14   48                                                       
CONECT   16   18   14   17   49                                             
CONECT   17   16   50                                                       
CONECT   18    9   16   19   51                                             
CONECT   19   18   52                                                       
CONECT   20   21   24    7   53                                             
CONECT   21   20   22    4   54                                             
CONECT   22   21   23   55                                                  
CONECT   23   22   24   56                                                  
CONECT   24   38   23   20   25                                             
CONECT   25   26   24   57                                                  
CONECT   26   25   36   27                                                  
CONECT   27   26   28   29   58                                             
CONECT   28   27   59                                                       
CONECT   29   35   27   30                                                  
CONECT   30   31   29   60                                                  
CONECT   31   30   32   61                                                  
CONECT   32   31   34   33                                                  
CONECT   33   32   62                                                       
CONECT   34   32   35   63                                                  
CONECT   35   34   29   64                                                  
CONECT   36   38   37   26                                                  
CONECT   37   36                                                            
CONECT   38   24   36                                                       
CONECT   39    3                                                            
CONECT   40    5                                                            
CONECT   41    7                                                            
CONECT   42    9                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   23                                                            
CONECT   57   25                                                            
CONECT   58   27                                                            
CONECT   59   28                                                            
CONECT   60   30                                                            
CONECT   61   31                                                            
CONECT   62   33                                                            
CONECT   63   34                                                            
CONECT   64   35                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  136    0
END

RDKit          3D

64 68  0  0  0  0  0  0  0  0999 V2000
   -4.0690    4.0278   -2.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9486    3.8538   -2.6396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458    4.4620   -3.7665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9087    2.9782   -2.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116    2.0643   -1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5146    1.1193   -0.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2534    0.8846   -1.2286 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4083    0.0561   -2.3920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5354   -1.3346   -2.0707 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7943   -1.6180   -1.4641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9367   -3.0169   -1.1398 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2753   -3.1902   -0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3083   -2.3257    0.7292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8769   -3.8774   -2.4071 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9477   -5.2675   -2.0911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5741   -3.5957   -3.1567 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5882   -4.3086   -4.4034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4088   -2.0987   -3.4033 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8667   -1.8720   -4.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4508    2.1676   -1.6764 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4771    3.0895   -2.4947 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1399    4.4372   -2.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9806    4.4088   -1.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0366    3.0504   -0.5502 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4227    3.0144    0.7909 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2572    2.4663    1.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0611    2.0531    3.0870 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2752    3.0381    3.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3635    0.7026    3.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0362    0.6118    3.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6608   -0.6266    2.8911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8888   -1.7810    2.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4650   -2.9972    2.6361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4910   -1.7220    3.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1193   -0.4816    3.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5127    2.2230    0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049    1.7038    1.4453 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3891    2.6559   -0.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3273    4.9888   -4.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3285    1.9792   -0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3902    0.3650   -0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -1.6186   -1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1358   -3.2895   -0.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4206   -4.2177   -0.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1153   -2.9073   -1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0710   -1.4441    0.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7267   -3.6498   -3.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7220   -5.7345   -2.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2826   -3.9934   -2.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1851   -3.9711   -4.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668   -1.7531   -4.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522   -0.9013   -4.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2820    1.8664   -2.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    2.8462   -3.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0778    5.3220   -2.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5251    5.2642   -0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5963    3.2996    1.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0142    2.0019    3.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0019    2.6379    4.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6474    1.5125    2.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418   -0.6749    2.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3287   -2.8427    2.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781   -2.6358    2.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2057   -0.4442    3.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 31  2  0
  5  4  2  0
 31 32  1  0
 20 21  1  0
 32 34  2  0
 26 25  2  0
 34 35  1  0
 35 29  2  0
 32 33  1  0
 24 38  1  1
  7  8  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  1  0
 38 36  1  0
 36 37  2  0
 36 26  1  0
 26 27  1  0
 21  4  1  0
  9 18  1  0
 18 16  1  0
 16 14  1  0
 14 11  1  0
 11 10  1  0
 10  9  1  0
 14 15  1  0
 16 17  1  0
 18 19  1  0
 27 28  1  0
 12 13  1  0
 20  7  1  0
  4  2  1  0
 27 29  1  0
  2  3  1  0
  7  6  1  0
  2  1  2  0
 29 30  1  0
 21 54  1  6
  6  5  1  0
 20 53  1  6
 24 25  1  0
 11 12  1  0
  9  8  1  0
 25 57  1  0
  7 41  1  1
  5 40  1  0
 22 55  1  0
 23 56  1  0
 27 58  1  1
 28 59  1  0
 30 60  1  0
 31 61  1  0
 34 63  1  0
 35 64  1  0
 33 62  1  0
  9 42  1  1
 14 47  1  6
 15 48  1  0
 16 49  1  1
 17 50  1  0
 18 51  1  6
 19 52  1  0
 12 44  1  0
 12 45  1  0
 11 43  1  1
 13 46  1  0
  3 39  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆O₁₃

Average Mass

534.4700 Da

Monoisotopic Mass

534.13734 Da

IUPAC Name

(1S,4aS,7R,7aS)-4'-[(S)-hydroxy(4-hydroxyphenyl)methyl]-5'-oxo-1-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylic acid

Traditional Name

(1S,4aS,7R,7aS)-4'-[(S)-hydroxy(4-hydroxyphenyl)methyl]-5'-oxo-1-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])O[C@@]([H])(O[C@@]2([H])O[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])[C@@]2([H])[C@]1([H])C([H])=C([H])[C@]21OC(=O)C(=C1[H])[C@@]([H])(O[H])C1=C([H])C([H])=C(O[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C25H26O13/c26-8-15-18(29)19(30)20(31)24(36-15)37-23-16-12(14(9-35-23)21(32)33)5-6-25(16)7-13(22(34)38-25)17(28)10-1-3-11(27)4-2-10/h1-7,9,12,15-20,23-24,26-31H,8H2,(H,32,33)/t12-,15+,16-,17+,18+,19-,20+,23+,24-,25-/m1/s1

InChI Key

FTQHRAAKMDKGHW-PDAMXGFISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Morinda morindoides	JEOL database	Cimanga, K., et al, J. Nat. Prod. 66, 97 (2003)

Chemical Taxonomy

Classification

Not classified

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	-0.3	ALOGPS
logP	-0.95	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.05	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	212.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	124.11 m³·mol⁻¹	ChemAxon
Polarizability	49.72 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

Not Available

References

General References

Cimanga, K., et al. (2003). Cimanga, K., et al, J. Nat. Prod. 66, 97 (2003). J. Nat. Prod..

Showing NP-Card for Gaertneric acid (NP0026342)

MOL for NP0026342 (Gaertneric acid)

3D MOL for NP0026342 (Gaertneric acid)

3D SDF for NP0026342 (Gaertneric acid)

3D-SDF for NP0026342 (Gaertneric acid)

PDB for NP0026342 (Gaertneric acid)

3D PDB for NP0026342 (Gaertneric acid)

SMILES for NP0026342 (Gaertneric acid)

INCHI for NP0026342 (Gaertneric acid)

Structure for NP0026342 (Gaertneric acid)

3D Structure for NP0026342 (Gaertneric acid)