NP-MRD: Showing NP-Card for (-)-rotoic acid (NP0029585)

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Record Information

Version

2.0

Created at

2021-06-19 21:10:44 UTC

Updated at

2021-06-29 23:57:02 UTC

NP-MRD ID

NP0029585

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-rotoic acid

Provided By

JEOL Database JEOL Logo

Description

(?)-Rotoic acid is also known as (?)-Rotoate. (-)-rotoic acid is found in Lonchocarpus nicou. (-)-rotoic acid was first documented in 2006 (Lawson, M. A., et al.). Based on a literature review very few articles have been published on (?)-Rotoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123103D          

 53 56  0  0  0  0            999 V2000
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   -2.5874    3.3520   -1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8828    4.6748   -0.8832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6402    2.4624    0.2049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2902    1.8184    0.5740 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3369    1.9422    2.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801    2.7883    2.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6099    3.1823    3.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7401    2.7171    4.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4775    1.4452    3.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2586   -0.6321    2.2315 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306192123103D          

 53 56  0  0  0  0            999 V2000
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    0.1292   -1.5093    4.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465   -1.5971    3.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8213   -5.3847    2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482   -7.2802    1.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8393   -8.3603    0.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5022   -7.3889    0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537   -4.2009   -3.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787   -3.0556   -3.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8869   -3.0009   -2.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1478   -1.9824   -1.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 10 14  2  0  0  0  0
  7  6  2  0  0  0  0
 29 28  1  0  0  0  0
 27 24  2  0  0  0  0
 19 18  1  0  0  0  0
 24 21  1  0  0  0  0
 18 17  1  0  0  0  0
  6  5  1  0  0  0  0
  5  4  1  0  0  0  0
  4 31  1  0  0  0  0
 31  7  1  0  0  0  0
 21 20  2  0  0  0  0
  4  2  1  0  0  0  0
 20 19  1  0  0  0  0
 16 43  1  6  0  0  0
  2  3  1  0  0  0  0
 16 15  1  0  0  0  0
  2  1  2  3  0  0  0
 16 29  1  0  0  0  0
 10 11  1  0  0  0  0
 15 14  1  0  0  0  0
 11 13  1  0  0  0  0
 14  6  1  0  0  0  0
 29 30  2  0  0  0  0
 19 28  2  0  0  0  0
 11 12  2  0  0  0  0
  7  8  1  0  0  0  0
 21 22  1  0  0  0  0
 16 17  1  0  0  0  0
 24 25  1  0  0  0  0
  8  9  2  0  0  0  0
 25 26  1  0  0  0  0
 28 27  1  0  0  0  0
 22 23  1  0  0  0  0
 17 44  1  0  0  0  0
 17 45  1  0  0  0  0
 27 53  1  0  0  0  0
 20 46  1  0  0  0  0
  8 40  1  0  0  0  0
  9 41  1  0  0  0  0
  5 38  1  0  0  0  0
  5 39  1  0  0  0  0
  4 37  1  6  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
  3 36  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
 13 42  1  0  0  0  0
 26 50  1  0  0  0  0
 26 51  1  0  0  0  0
 26 52  1  0  0  0  0
 23 47  1  0  0  0  0
 23 48  1  0  0  0  0
 23 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029585

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C(O[C@@]2([H])C(=O)C3=C(OC2([H])[H])C([H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C3[H])C2=C(O[C@@]([H])(C(=C([H])[H])C([H])([H])[H])C2([H])[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O8/c1-11(2)16-8-14-15(30-16)6-5-12(23(25)26)22(14)31-20-10-29-17-9-19(28-4)18(27-3)7-13(17)21(20)24/h5-7,9,16,20H,1,8,10H2,2-4H3,(H,25,26)/t16-,20-/m1/s1

> <INCHI_KEY>
PIQZKVNWXMPJLU-OXQOHEQNSA-N

> <FORMULA>
C23H22O8

> <MOLECULAR_WEIGHT>
426.421

> <EXACT_MASS>
426.131467668

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
44.42783670084714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-4-{[(3R)-6,7-dimethoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
3.189392768666667

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.689685545414186

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9690069851438263

> <JCHEM_PKA_STRONGEST_BASIC>
-4.221588152248825

> <JCHEM_POLAR_SURFACE_AREA>
100.52000000000002

> <JCHEM_REFRACTIVITY>
109.73269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-4-{[(3R)-6,7-dimethoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl]oxy}-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.1564    2.9873   -2.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5874    3.3520   -1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8828    4.6748   -0.8832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6402    2.4624    0.2049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2902    1.8184    0.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369    1.9422    2.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801    2.7883    2.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6099    3.1823    3.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7401    2.7171    4.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6604    1.8634    4.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2755    1.4239    5.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0680    0.5023    5.3930 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1730    2.1838    6.5395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775    1.4452    3.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6020    0.6830    2.6795 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2586   -0.6321    2.2315 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6795   -1.6704    3.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3730   -3.0035    2.8352 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9408   -3.3140    1.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1273   -4.6698    1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047   -5.0765    0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9348   -6.3850   -0.1934 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5803   -7.3900    0.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0902   -4.1080   -0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6492   -4.5908   -1.9572 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092   -3.6456   -2.9135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8800   -2.7517   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2984   -2.3617    0.6783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0188   -0.9355    0.9481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463   -0.0839    0.1253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225    3.2331    1.3364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6748    2.0395   -2.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1233    3.6304   -3.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8751    5.2338   -1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8413    4.5324   -0.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3807    5.3006   -0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3810    1.6642    0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4287    2.3610    0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2618    0.7836    0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4275    3.8535    3.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997    3.0387    5.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8521    1.8128    7.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8100   -0.7462    2.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292   -1.5093    4.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465   -1.5971    3.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8213   -5.3847    2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482   -7.2802    1.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8393   -8.3603    0.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5022   -7.3889    0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537   -4.2009   -3.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787   -3.0556   -3.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8869   -3.0009   -2.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1478   -1.9824   -1.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10 14  2  0
  7  6  2  0
 29 28  1  0
 27 24  2  0
 19 18  1  0
 24 21  1  0
 18 17  1  0
  6  5  1  0
  5  4  1  0
  4 31  1  0
 31  7  1  0
 21 20  2  0
  4  2  1  0
 20 19  1  0
 16 43  1  6
  2  3  1  0
 16 15  1  0
  2  1  2  3
 16 29  1  0
 10 11  1  0
 15 14  1  0
 11 13  1  0
 14  6  1  0
 29 30  2  0
 19 28  2  0
 11 12  2  0
  7  8  1  0
 21 22  1  0
 16 17  1  0
 24 25  1  0
  8  9  2  0
 25 26  1  0
 28 27  1  0
 22 23  1  0
 17 44  1  0
 17 45  1  0
 27 53  1  0
 20 46  1  0
  8 40  1  0
  9 41  1  0
  5 38  1  0
  5 39  1  0
  4 37  1  6
  3 34  1  0
  3 35  1  0
  3 36  1  0
  1 32  1  0
  1 33  1  0
 13 42  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 23 47  1  0
 23 48  1  0
 23 49  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  C   UNK     0      -3.156   2.987  -2.184  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.587   3.352  -1.022  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.883   4.675  -0.883  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.640   2.462   0.205  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.290   1.818   0.574  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.337   1.942   2.053  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.380   2.788   2.397  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.610   3.182   3.698  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.740   2.717   4.686  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.660   1.863   4.360  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.276   1.424   5.431  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.068   0.502   5.393  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.173   2.184   6.540  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.478   1.445   3.028  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.602   0.683   2.680  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.259  -0.632   2.232  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.680  -1.670   3.263  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.373  -3.003   2.835  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.941  -3.314   1.629  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.127  -4.670   1.361  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.705  -5.077   0.153  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.935  -6.385  -0.193  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.580  -7.390   0.746  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.090  -4.108  -0.800  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.649  -4.591  -1.957  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.109  -3.646  -2.914  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.880  -2.752  -0.533  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.298  -2.362   0.678  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.019  -0.936   0.948  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.346  -0.084   0.125  0.00  0.00           O+0
HETATM   31  O   UNK     0      -3.123   3.233   1.336  0.00  0.00           O+0
HETATM   32  H   UNK     0      -3.675   2.039  -2.295  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.123   3.630  -3.059  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.875   5.234  -1.825  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.841   4.532  -0.580  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.381   5.301  -0.136  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.381   1.664   0.051  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.429   2.361   0.173  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.262   0.784   0.225  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.428   3.853   3.939  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.900   3.039   5.713  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.852   1.813   7.141  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.810  -0.746   2.002  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.129  -1.509   4.196  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.746  -1.597   3.514  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.821  -5.385   2.118  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.148  -7.280   1.676  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.839  -8.360   0.311  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.502  -7.389   0.937  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.554  -4.201  -3.745  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.279  -3.056  -3.315  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.887  -3.001  -2.491  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.148  -1.982  -1.250  0.00  0.00           H+0
CONECT    1    2   32   33                                                  
CONECT    2    4    3    1                                                  
CONECT    3    2   34   35   36                                             
CONECT    4    5   31    2   37                                             
CONECT    5    6    4   38   39                                             
CONECT    6    7    5   14                                                  
CONECT    7    6   31    8                                                  
CONECT    8    7    9   40                                                  
CONECT    9   10    8   41                                                  
CONECT   10    9   14   11                                                  
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   11   42                                                       
CONECT   14   10   15    6                                                  
CONECT   15   16   14                                                       
CONECT   16   43   15   29   17                                             
CONECT   17   18   16   44   45                                             
CONECT   18   19   17                                                       
CONECT   19   18   20   28                                                  
CONECT   20   21   19   46                                                  
CONECT   21   24   20   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   47   48   49                                             
CONECT   24   27   21   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   50   51   52                                             
CONECT   27   24   28   53                                                  
CONECT   28   29   19   27                                                  
CONECT   29   28   16   30                                                  
CONECT   30   29                                                            
CONECT   31    4    7                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    5                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42   13                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   17                                                            
CONECT   46   20                                                            
CONECT   47   23                                                            
CONECT   48   23                                                            
CONECT   49   23                                                            
CONECT   50   26                                                            
CONECT   51   26                                                            
CONECT   52   26                                                            
CONECT   53   27                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  112    0
END

RDKit          3D

53 56  0  0  0  0  0  0  0  0999 V2000
   -3.1564    2.9873   -2.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5874    3.3520   -1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8828    4.6748   -0.8832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6402    2.4624    0.2049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2902    1.8184    0.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369    1.9422    2.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801    2.7883    2.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6099    3.1823    3.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7401    2.7171    4.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6604    1.8634    4.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2755    1.4239    5.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0680    0.5023    5.3930 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1730    2.1838    6.5395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775    1.4452    3.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6020    0.6830    2.6795 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2586   -0.6321    2.2315 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6795   -1.6704    3.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3730   -3.0035    2.8352 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9408   -3.3140    1.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1273   -4.6698    1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047   -5.0765    0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9348   -6.3850   -0.1934 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5803   -7.3900    0.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0902   -4.1080   -0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6492   -4.5908   -1.9572 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092   -3.6456   -2.9135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8800   -2.7517   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2984   -2.3617    0.6783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0188   -0.9355    0.9481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463   -0.0839    0.1253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225    3.2331    1.3364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6748    2.0395   -2.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1233    3.6304   -3.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8751    5.2338   -1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8413    4.5324   -0.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3807    5.3006   -0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3810    1.6642    0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4287    2.3610    0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2618    0.7836    0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4275    3.8535    3.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997    3.0387    5.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8521    1.8128    7.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8100   -0.7462    2.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292   -1.5093    4.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465   -1.5971    3.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8213   -5.3847    2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482   -7.2802    1.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8393   -8.3603    0.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5022   -7.3889    0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537   -4.2009   -3.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787   -3.0556   -3.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8869   -3.0009   -2.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1478   -1.9824   -1.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10 14  2  0
  7  6  2  0
 29 28  1  0
 27 24  2  0
 19 18  1  0
 24 21  1  0
 18 17  1  0
  6  5  1  0
  5  4  1  0
  4 31  1  0
 31  7  1  0
 21 20  2  0
  4  2  1  0
 20 19  1  0
 16 43  1  6
  2  3  1  0
 16 15  1  0
  2  1  2  3
 16 29  1  0
 10 11  1  0
 15 14  1  0
 11 13  1  0
 14  6  1  0
 29 30  2  0
 19 28  2  0
 11 12  2  0
  7  8  1  0
 21 22  1  0
 16 17  1  0
 24 25  1  0
  8  9  2  0
 25 26  1  0
 28 27  1  0
 22 23  1  0
 17 44  1  0
 17 45  1  0
 27 53  1  0
 20 46  1  0
  8 40  1  0
  9 41  1  0
  5 38  1  0
  5 39  1  0
  4 37  1  6
  3 34  1  0
  3 35  1  0
  3 36  1  0
  1 32  1  0
  1 33  1  0
 13 42  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
M  END

View in JSmol

Synonyms

Value	Source
(?)-rotoate	Generator

Chemical Formula

C₂₃H₂₂O₈

Average Mass

426.4210 Da

Monoisotopic Mass

426.13147 Da

IUPAC Name

(2R)-4-{[(3R)-6,7-dimethoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid

Traditional Name

(2R)-4-{[(3R)-6,7-dimethoxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl]oxy}-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C(O[C@@]2([H])C(=O)C3=C(OC2([H])[H])C([H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C3[H])C2=C(O[C@@]([H])(C(=C([H])[H])C([H])([H])[H])C2([H])[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C23H22O8/c1-11(2)16-8-14-15(30-16)6-5-12(23(25)26)22(14)31-20-10-29-17-9-19(28-4)18(27-3)7-13(17)21(20)24/h5-7,9,16,20H,1,8,10H2,2-4H3,(H,25,26)/t16-,20-/m1/s1

InChI Key

PIQZKVNWXMPJLU-OXQOHEQNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Lonchocarpus nicou	JEOL database	Lawson, M. A., et al, Tetrahedron Letts. 47, 451 (2006)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Chromones

Alternative Parents

Substituents

Chromone
Coumaran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Benzenoid
Ketone
Carboxylic acid derivative
Carboxylic acid
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aldehyde
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	3.11	ALOGPS
logP	3.19	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.97	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	100.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	109.73 m³·mol⁻¹	ChemAxon
Polarizability	44.43 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

28283215

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bracket

METLIN ID

Not Available

PubChem Compound

101384091

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lawson, M. A., et al. (2006). Lawson, M. A., et al, Tetrahedron Letts. 47, 451 (2006). Tetrahedron Lett.

Showing NP-Card for (-)-rotoic acid (NP0029585)

MOL for NP0029585 ((-)-rotoic acid)

3D MOL for NP0029585 ((-)-rotoic acid)

3D SDF for NP0029585 ((-)-rotoic acid)

3D-SDF for NP0029585 ((-)-rotoic acid)

PDB for NP0029585 ((-)-rotoic acid)

3D PDB for NP0029585 ((-)-rotoic acid)

SMILES for NP0029585 ((-)-rotoic acid)

INCHI for NP0029585 ((-)-rotoic acid)

Structure for NP0029585 ((-)-rotoic acid)

3D Structure for NP0029585 ((-)-rotoic acid)