NP-MRD: Showing NP-Card for grandilodine B (NP0036038)

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Record Information

Version

2.0

Created at

2021-06-20 19:19:07 UTC

Updated at

2021-06-30 00:07:28 UTC

NP-MRD ID

NP0036038

Secondary Accession Numbers

None

Natural Product Identification

Common Name

grandilodine B

Provided By

JEOL Database JEOL Logo

Description

Grandilodine B, (rel)-, also known as grandilodine b, belongs to the class of organic compounds known as indolecarboxylic acids. Indolecarboxylic acids are compounds containing a carboxylic acid group linked to an indole. grandilodine B is found in Kopsia grandifolia and Kopsia lapidilecta. grandilodine B was first documented in 2011 (Yap, W. -S., et al.). Based on a literature review very few articles have been published on Grandilodine B, (rel)-.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121193D          

 59 63  0  0  0  0            999 V2000
   -2.2350   -1.4227   -3.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816   -1.4052   -2.5585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2099   -0.7358   -2.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1356   -0.1965   -3.7830 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6404   -0.7978   -1.4748 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0409   -1.2462   -1.9231 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0883   -0.1345   -1.9162 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1215   -0.4283   -2.9792 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3498   -0.6329   -2.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2609   -0.4840   -1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2127   -0.5817   -0.2940 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9351   -0.2136   -0.7331 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5430    0.0831    0.6337 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.2871    2.5707    1.4188 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8508    1.4990   -1.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
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 31 26  1  1  0  0  0
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  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 21 22  1  0  0  0  0
 31 32  1  0  0  0  0
 20 25  1  0  0  0  0
  7 33  1  0  0  0  0
  5  3  1  0  0  0  0
 23 24  1  0  0  0  0
 26 27  1  0  0  0  0
 32 33  1  0  0  0  0
  7  6  1  0  0  0  0
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  6  5  1  0  0  0  0
 18 19  1  0  0  0  0
  5 31  1  0  0  0  0
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M  END

     RDKit          3D

 59 63  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306202121193D          

 59 63  0  0  0  0            999 V2000
   -2.2350   -1.4227   -3.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816   -1.4052   -2.5585 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2549    1.9612   -2.3672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1104    2.6945   -3.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5348    0.5221   -0.6036 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3887    1.6769   -1.2089 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4979    1.2535   -2.1740 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7574   -1.9657   -4.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4920   -0.4047   -4.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1563   -1.9446   -3.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2325   -1.6414   -0.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3727   -2.0847   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9774   -1.6985   -2.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -0.4659   -4.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612   -0.8540   -3.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5299    1.1721    0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3545   -0.2555    1.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849   -0.7330    2.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336   -1.5904    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3462    4.2055    2.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3860    4.4576    1.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1153    3.5108    3.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3929   -1.4738    3.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8984   -2.1363    3.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8543   -1.3600    2.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5552    0.0381    0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5258    2.9816   -4.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4692    3.6046   -2.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490    2.0743   -3.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7859    2.4333   -1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816    2.2573   -0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2871    2.0182   -2.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0939    1.2942   -3.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 26  1  1  0  0  0
 15 20  1  0  0  0  0
 22 23  2  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 20 21  2  0  0  0  0
 15 16  1  1  0  0  0
 21 22  1  0  0  0  0
 31 32  1  0  0  0  0
 20 25  1  0  0  0  0
  7 33  1  0  0  0  0
  5  3  1  0  0  0  0
 23 24  1  0  0  0  0
 26 27  1  0  0  0  0
 32 33  1  0  0  0  0
  7  6  1  0  0  0  0
 16 18  1  0  0  0  0
  6  5  1  0  0  0  0
 18 19  1  0  0  0  0
  5 31  1  0  0  0  0
 27 29  1  0  0  0  0
 31 15  1  0  0  0  0
 29 30  1  0  0  0  0
 15 14  1  0  0  0  0
 16 17  2  0  0  0  0
 14 13  1  0  0  0  0
  3  4  2  0  0  0  0
 13 12  1  0  0  0  0
  3  2  1  0  0  0  0
 12  7  1  0  0  0  0
 27 28  2  0  0  0  0
 24 25  2  0  0  0  0
  2  1  1  0  0  0  0
 25 26  1  0  0  0  0
 10 11  2  0  0  0  0
 22 50  1  0  0  0  0
 23 51  1  0  0  0  0
 24 52  1  0  0  0  0
 21 49  1  0  0  0  0
  6 38  1  0  0  0  0
  6 39  1  0  0  0  0
  5 37  1  1  0  0  0
 14 44  1  0  0  0  0
 14 45  1  0  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
  8 40  1  0  0  0  0
  9 41  1  0  0  0  0
 32 56  1  0  0  0  0
 32 57  1  0  0  0  0
 33 58  1  0  0  0  0
 33 59  1  0  0  0  0
 19 46  1  0  0  0  0
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 19 48  1  0  0  0  0
 30 53  1  0  0  0  0
 30 54  1  0  0  0  0
 30 55  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036038

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])[C@@]23N(C1=O)C([H])([H])C([H])([H])[C@]1(C(=O)OC([H])([H])[H])C4=C([H])C([H])=C([H])C([H])=C4N(C(=O)OC([H])([H])[H])[C@]1(C([H])([H])C2([H])[H])[C@@]([H])(C(=O)OC([H])([H])[H])C3([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H26N2O7/c1-31-19(28)16-14-22-9-8-18(27)25(22)13-12-23(20(29)32-2)15-6-4-5-7-17(15)26(21(30)33-3)24(16,23)11-10-22/h4-9,16H,10-14H2,1-3H3/t16-,22-,23-,24-/m1/s1

> <INCHI_KEY>
VOHFPFMHDXIAOK-JUJUEEDWSA-N

> <FORMULA>
C24H26N2O7

> <MOLECULAR_WEIGHT>
454.479

> <EXACT_MASS>
454.174001185

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.71564652867318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,9,18-trimethyl (1R,9S,16R,18S)-13-oxo-2,12-diazapentacyclo[14.2.2.0^{1,9}.0^{3,8}.0^{12,16}]icosa-3,5,7,14-tetraene-2,9,18-tricarboxylate

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
1.4422395896666658

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.10576551497963071

> <JCHEM_POLAR_SURFACE_AREA>
102.45

> <JCHEM_REFRACTIVITY>
115.745

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,9,18-trimethyl (1R,9S,16R,18S)-13-oxo-2,12-diazapentacyclo[14.2.2.0^{1,9}.0^{3,8}.0^{12,16}]icosa-3,5,7,14-tetraene-2,9,18-tricarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 63  0  0  0  0  0  0  0  0999 V2000
   -2.2350   -1.4227   -3.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0883   -0.1345   -1.9162 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1215   -0.4283   -2.9792 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3498   -0.6329   -2.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2609   -0.4840   -1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2127   -0.5817   -0.2940 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9351   -0.2136   -0.7331 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5430    0.0831    0.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502   -0.5770    1.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9794    0.2764    0.9228 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1471    1.5796    1.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9447    1.6843    2.7085 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2871    2.5707    1.4188 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3556    3.7466    2.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902   -0.3712    1.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4523   -1.1613    2.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7447   -1.5222    2.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8508   -1.0789    2.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6801   -0.2771    1.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3938    0.0634    0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9686    0.8080   -0.4204 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8508    1.4990   -1.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0401    1.6893   -1.0084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2549    1.9612   -2.3672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1104    2.6945   -3.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5348    0.5221   -0.6036 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3887    1.6769   -1.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4979    1.2535   -2.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7574   -1.9657   -4.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4920   -0.4047   -4.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1563   -1.9446   -3.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2325   -1.6414   -0.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3727   -2.0847   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9774   -1.6985   -2.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -0.4659   -4.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612   -0.8540   -3.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5299    1.1721    0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3545   -0.2555    1.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849   -0.7330    2.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336   -1.5904    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3462    4.2055    2.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3860    4.4576    1.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1153    3.5108    3.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3929   -1.4738    3.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8984   -2.1363    3.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8543   -1.3600    2.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5552    0.0381    0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5258    2.9816   -4.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4692    3.6046   -2.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490    2.0743   -3.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7859    2.4333   -1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816    2.2573   -0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2871    2.0182   -2.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0939    1.2942   -3.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 26  1  1
 15 20  1  0
 22 23  2  0
  7  8  1  6
  8  9  2  0
  9 10  1  0
 10 12  1  0
 20 21  2  0
 15 16  1  1
 21 22  1  0
 31 32  1  0
 20 25  1  0
  7 33  1  0
  5  3  1  0
 23 24  1  0
 26 27  1  0
 32 33  1  0
  7  6  1  0
 16 18  1  0
  6  5  1  0
 18 19  1  0
  5 31  1  0
 27 29  1  0
 31 15  1  0
 29 30  1  0
 15 14  1  0
 16 17  2  0
 14 13  1  0
  3  4  2  0
 13 12  1  0
  3  2  1  0
 12  7  1  0
 27 28  2  0
 24 25  2  0
  2  1  1  0
 25 26  1  0
 10 11  2  0
 22 50  1  0
 23 51  1  0
 24 52  1  0
 21 49  1  0
  6 38  1  0
  6 39  1  0
  5 37  1  1
 14 44  1  0
 14 45  1  0
 13 42  1  0
 13 43  1  0
  8 40  1  0
  9 41  1  0
 32 56  1  0
 32 57  1  0
 33 58  1  0
 33 59  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 30 53  1  0
 30 54  1  0
 30 55  1  0
  1 34  1  0
  1 35  1  0
  1 36  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  C   UNK     0      -2.235  -1.423  -3.703  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.382  -1.405  -2.559  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.210  -0.736  -2.740  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.136  -0.197  -3.783  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.640  -0.798  -1.475  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.041  -1.246  -1.923  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.088  -0.135  -1.916  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.122  -0.428  -2.979  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.350  -0.633  -2.499  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.261  -0.484  -1.046  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.213  -0.582  -0.294  0.00  0.00           O+0
HETATM   12  N   UNK     0       3.935  -0.214  -0.733  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.543   0.083   0.634  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.250  -0.577   1.127  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.979   0.276   0.923  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.147   1.580   1.781  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.945   1.684   2.708  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.287   2.571   1.419  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.356   3.747   2.227  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.290  -0.371   1.458  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.452  -1.161   2.591  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.745  -1.522   2.970  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.851  -1.079   2.234  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.680  -0.277   1.102  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.394   0.063   0.715  0.00  0.00           C+0
HETATM   26  N   UNK     0      -0.969   0.808  -0.420  0.00  0.00           N+0
HETATM   27  C   UNK     0      -1.851   1.499  -1.237  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.040   1.689  -1.008  0.00  0.00           O+0
HETATM   29  O   UNK     0      -1.255   1.961  -2.367  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.110   2.695  -3.245  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.535   0.522  -0.604  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.389   1.677  -1.209  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.498   1.254  -2.174  0.00  0.00           C+0
HETATM   34  H   UNK     0      -1.757  -1.966  -4.525  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.492  -0.405  -4.010  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.156  -1.945  -3.431  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.233  -1.641  -0.899  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.373  -2.085  -1.297  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.977  -1.698  -2.924  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.879  -0.466  -4.034  0.00  0.00           H+0
HETATM   41  H   UNK     0       6.261  -0.854  -3.024  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.530   1.172   0.733  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.354  -0.256   1.290  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.385  -0.733   2.208  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.134  -1.590   0.734  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.346   4.205   2.150  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.386   4.458   1.852  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.115   3.511   3.268  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.393  -1.474   3.196  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.898  -2.136   3.855  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.854  -1.360   2.547  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.555   0.038   0.544  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.526   2.982  -4.123  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.469   3.605  -2.755  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.949   2.074  -3.576  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.786   2.433  -1.712  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.882   2.257  -0.425  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.287   2.018  -2.148  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.094   1.294  -3.194  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    3    1                                                       
CONECT    3    5    4    2                                                  
CONECT    4    3                                                            
CONECT    5    3    6   31   37                                             
CONECT    6    7    5   38   39                                             
CONECT    7    8   33    6   12                                             
CONECT    8    7    9   40                                                  
CONECT    9    8   10   41                                                  
CONECT   10    9   12   11                                                  
CONECT   11   10                                                            
CONECT   12   10   13    7                                                  
CONECT   13   14   12   42   43                                             
CONECT   14   15   13   44   45                                             
CONECT   15   20   16   31   14                                             
CONECT   16   15   18   17                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   46   47   48                                             
CONECT   20   15   21   25                                                  
CONECT   21   20   22   49                                                  
CONECT   22   23   21   50                                                  
CONECT   23   22   24   51                                                  
CONECT   24   23   25   52                                                  
CONECT   25   20   24   26                                                  
CONECT   26   31   27   25                                                  
CONECT   27   26   29   28                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   53   54   55                                             
CONECT   31   26   32    5   15                                             
CONECT   32   31   33   56   57                                             
CONECT   33    7   32   58   59                                             
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39    6                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   19                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   21                                                            
CONECT   50   22                                                            
CONECT   51   23                                                            
CONECT   52   24                                                            
CONECT   53   30                                                            
CONECT   54   30                                                            
CONECT   55   30                                                            
CONECT   56   32                                                            
CONECT   57   32                                                            
CONECT   58   33                                                            
CONECT   59   33                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  126    0
END

RDKit          3D

59 63  0  0  0  0  0  0  0  0999 V2000
   -2.2350   -1.4227   -3.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816   -1.4052   -2.5585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2099   -0.7358   -2.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1356   -0.1965   -3.7830 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6404   -0.7978   -1.4748 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0409   -1.2462   -1.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0883   -0.1345   -1.9162 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1215   -0.4283   -2.9792 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3498   -0.6329   -2.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2609   -0.4840   -1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2127   -0.5817   -0.2940 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9351   -0.2136   -0.7331 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5430    0.0831    0.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502   -0.5770    1.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9794    0.2764    0.9228 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1471    1.5796    1.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9447    1.6843    2.7085 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2871    2.5707    1.4188 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3556    3.7466    2.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902   -0.3712    1.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4523   -1.1613    2.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7447   -1.5222    2.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8508   -1.0789    2.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6801   -0.2771    1.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3938    0.0634    0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9686    0.8080   -0.4204 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8508    1.4990   -1.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0401    1.6893   -1.0084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2549    1.9612   -2.3672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1104    2.6945   -3.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5348    0.5221   -0.6036 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3887    1.6769   -1.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4979    1.2535   -2.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7574   -1.9657   -4.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4920   -0.4047   -4.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1563   -1.9446   -3.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2325   -1.6414   -0.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3727   -2.0847   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9774   -1.6985   -2.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -0.4659   -4.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612   -0.8540   -3.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5299    1.1721    0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3545   -0.2555    1.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849   -0.7330    2.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336   -1.5904    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3462    4.2055    2.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3860    4.4576    1.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1153    3.5108    3.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3929   -1.4738    3.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8984   -2.1363    3.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8543   -1.3600    2.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5552    0.0381    0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5258    2.9816   -4.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4692    3.6046   -2.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490    2.0743   -3.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7859    2.4333   -1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816    2.2573   -0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2871    2.0182   -2.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0939    1.2942   -3.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 26  1  1
 15 20  1  0
 22 23  2  0
  7  8  1  6
  8  9  2  0
  9 10  1  0
 10 12  1  0
 20 21  2  0
 15 16  1  1
 21 22  1  0
 31 32  1  0
 20 25  1  0
  7 33  1  0
  5  3  1  0
 23 24  1  0
 26 27  1  0
 32 33  1  0
  7  6  1  0
 16 18  1  0
  6  5  1  0
 18 19  1  0
  5 31  1  0
 27 29  1  0
 31 15  1  0
 29 30  1  0
 15 14  1  0
 16 17  2  0
 14 13  1  0
  3  4  2  0
 13 12  1  0
  3  2  1  0
 12  7  1  0
 27 28  2  0
 24 25  2  0
  2  1  1  0
 25 26  1  0
 10 11  2  0
 22 50  1  0
 23 51  1  0
 24 52  1  0
 21 49  1  0
  6 38  1  0
  6 39  1  0
  5 37  1  1
 14 44  1  0
 14 45  1  0
 13 42  1  0
 13 43  1  0
  8 40  1  0
  9 41  1  0
 32 56  1  0
 32 57  1  0
 33 58  1  0
 33 59  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 30 53  1  0
 30 54  1  0
 30 55  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
Grandilodine b	MeSH

Chemical Formula

C₂₄H₂₆N₂O₇

Average Mass

454.4790 Da

Monoisotopic Mass

454.17400 Da

IUPAC Name

2,9,18-trimethyl (1R,9S,16R,18S)-13-oxo-2,12-diazapentacyclo[14.2.2.0^{1,9}.0^{3,8}.0^{12,16}]icosa-3,5,7,14-tetraene-2,9,18-tricarboxylate

Traditional Name

2,9,18-trimethyl (1R,9S,16R,18S)-13-oxo-2,12-diazapentacyclo[14.2.2.0^{1,9}.0^{3,8}.0^{12,16}]icosa-3,5,7,14-tetraene-2,9,18-tricarboxylate

CAS Registry Number

Not Available

SMILES

[H]C1=C([H])[C@@]23N(C1=O)C([H])([H])C([H])([H])[C@]1(C(=O)OC([H])([H])[H])C4=C([H])C([H])=C([H])C([H])=C4N(C(=O)OC([H])([H])[H])[C@]1(C([H])([H])C2([H])[H])[C@@]([H])(C(=O)OC([H])([H])[H])C3([H])[H]

InChI Identifier

InChI=1S/C24H26N2O7/c1-31-19(28)16-14-22-9-8-18(27)25(22)13-12-23(20(29)32-2)15-6-4-5-7-17(15)26(21(30)33-3)24(16,23)11-10-22/h4-9,16H,10-14H2,1-3H3/t16-,22-,23-,24-/m1/s1

InChI Key

VOHFPFMHDXIAOK-JUJUEEDWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Kopsia grandifolia	JEOL database	Yap, W. -S., et al, J. Nat. Prod. 74, 1309 (2011)
Kopsia lapidilecta	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxylic acids. Indolecarboxylic acids are compounds containing a carboxylic acid group linked to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic acids

Alternative Parents

Substituents

Indolecarboxylic acid
Dicarboxylic acid or derivatives
Benzenoid
Pyrroline
Tertiary carboxylic acid amide
Carbamic acid ester
Methyl ester
Carboxamide group
Carbonic acid derivative
Lactam
Carboxylic acid ester
Carboxylic acid derivative
Azacycle
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indolyl carboxylic acid (CHEBI:68088 )

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	1.44	ALOGPS
logP	1.44	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-0.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	102.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.74 m³·mol⁻¹	ChemAxon
Polarizability	45.72 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

25378962

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53356000

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yap, W. -S., et al. (2011). Yap, W. -S., et al, J. Nat. Prod. 74, 1309 (2011). J. Nat. Prod..

Showing NP-Card for grandilodine B (NP0036038)

MOL for NP0036038 (grandilodine B)

3D MOL for NP0036038 (grandilodine B)

3D SDF for NP0036038 (grandilodine B)

3D-SDF for NP0036038 (grandilodine B)

PDB for NP0036038 (grandilodine B)

3D PDB for NP0036038 (grandilodine B)

SMILES for NP0036038 (grandilodine B)

INCHI for NP0036038 (grandilodine B)

Structure for NP0036038 (grandilodine B)

3D Structure for NP0036038 (grandilodine B)