NP-MRD: Showing NP-Card for giluterrin (NP0332304)

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Record Information

Version

1.0

Created at

2024-01-04 04:16:38 UTC

Updated at

2024-04-19 10:02:39 UTC

NP-MRD ID

NP0332304

Secondary Accession Numbers

None

Natural Product Identification

Common Name

giluterrin

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01042404162D          

 37 42  0  0  1  0            999 V2000
    2.9760   -2.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116   -1.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1321   -1.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6170   -2.2281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2814   -2.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1622   -0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6773    0.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0129    1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267   -0.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0062   -1.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4541   -0.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    0.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326    0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972    1.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8187    0.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -0.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7005   -0.7881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -1.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5937   -1.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486   -2.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2966   -3.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4896   -3.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2347   -2.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676    0.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522    0.2730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2522    1.0980    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369    0.5279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5218   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423   -0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6778   -0.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1929   -1.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3724   -1.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522   -0.5520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2522   -1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  2  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
  7 26  1  0  0  0  0
 27 26  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 36 35  1  0  0  0  0
 27 36  1  0  0  0  0
 36  6  1  0  0  0  0
 36 37  1  1  0  0  0
M  END


  Mrv2104 01042404162D          

 37 42  0  0  1  0            999 V2000
    2.9760   -2.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116   -1.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1321   -1.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6170   -2.2281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2814   -2.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1622   -0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6773    0.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0129    1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267   -0.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0062   -1.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4541   -0.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    0.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326    0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972    1.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8187    0.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -0.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7005   -0.7881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -1.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5937   -1.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486   -2.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2966   -3.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4896   -3.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2347   -2.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676    0.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522    0.2730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2522    1.0980    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369    0.5279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5218   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423   -0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6778   -0.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1929   -1.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3724   -1.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522   -0.5520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2522   -1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  2  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
  7 26  1  0  0  0  0
 27 26  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 36 35  1  0  0  0  0
 27 36  1  0  0  0  0
 36  6  1  0  0  0  0
 36 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0332304

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12NC3=CC=CC=C3[C@]1(O)C1=C(O2)C(OC)=C(C2=C(NC3=C2C=CC=C3)C(C)(C)C=C)C(O)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C29H28N2O5/c1-6-28(2,3)26-19(15-11-7-9-13-17(15)30-26)20-22(32)24(35-5)21-25(23(20)34-4)36-27-29(21,33)16-12-8-10-14-18(16)31-27/h6-14,27,30-33H,1H2,2-5H3/t27-,29-/m0/s1

> <INCHI_KEY>
FSNAHOOBWDWUNP-YTMVLYRLSA-N

> <FORMULA>
C29H28N2O5

> <MOLECULAR_WEIGHT>
484.552

> <EXACT_MASS>
484.19982201

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
51.63716156400278

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,9S)-3,6-dimethoxy-5-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-8-oxa-10-azatetracyclo[7.7.0.0^{2,7}.0^{11,16}]hexadeca-2(7),3,5,11,13,15-hexaene-1,4-diol

> <JCHEM_LOGP>
4.805837964666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.071688217429223

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.808118171349506

> <JCHEM_PKA_STRONGEST_BASIC>
-1.483512791033836

> <JCHEM_POLAR_SURFACE_AREA>
95.97

> <JCHEM_REFRACTIVITY>
139.0224

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9S)-3,6-dimethoxy-5-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-8-oxa-10-azatetracyclo[7.7.0.0^{2,7}.0^{11,16}]hexadeca-2(7),3,5,11,13,15-hexaene-1,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JAN-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JAN-24         0                                  
HETATM    1  O   UNK     0       5.555  -4.481   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.182  -3.074   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.713  -2.913   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.618  -4.159   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.992  -5.566   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.340  -1.506   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.434  -0.260   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.903  -0.421   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.998   0.824   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.624   2.231   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.276  -1.828   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.745  -1.989   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.714  -0.845   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.035   0.662   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.541   0.341   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.355   2.168   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.528   0.982   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.498  -0.163   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       1.308  -1.471   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       1.469  -3.003   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.975  -3.323   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.451  -4.788   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.420  -5.932   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.914  -5.612   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.438  -4.147   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.340   0.985   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.804   0.510   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0       9.804   2.050   0.000  0.00  0.00           H+0
HETATM   29  N   UNK     0      11.269   0.985   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      12.174  -0.260   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.706  -0.421   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.332  -1.828   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.427  -3.074   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.895  -2.913   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.269  -1.506   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.804  -1.030   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.804  -2.570   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7   36                                                  
CONECT    7    6    8   26                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8    2   12                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17                                                            
CONECT   19   13   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   12   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26    7   27                                                       
CONECT   27   26   28   29   36                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30   36                                                  
CONECT   36   35   27    6   37                                             
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₂₈N₂O₅

Average Mass

484.5520 Da

Monoisotopic Mass

484.19982 Da

IUPAC Name

(1S,9S)-3,6-dimethoxy-5-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-8-oxa-10-azatetracyclo[7.7.0.0^{2,7}.0^{11,16}]hexadeca-2(7),3,5,11,13,15-hexaene-1,4-diol

Traditional Name

(1S,9S)-3,6-dimethoxy-5-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-8-oxa-10-azatetracyclo[7.7.0.0^{2,7}.0^{11,16}]hexadeca-2(7),3,5,11,13,15-hexaene-1,4-diol

CAS Registry Number

Not Available

SMILES

[H][C@@]12NC3=CC=CC=C3[C@]1(O)C1=C(O2)C(OC)=C(C2=C(NC3=C2C=CC=C3)C(C)(C)C=C)C(O)=C1OC

InChI Identifier

InChI=1S/C29H28N2O5/c1-6-28(2,3)26-19(15-11-7-9-13-17(15)30-26)20-22(32)24(35-5)21-25(23(20)34-4)36-27-29(21,33)16-12-8-10-14-18(16)31-27/h6-14,27,30-33H,1H2,2-5H3/t27-,29-/m0/s1

InChI Key

FSNAHOOBWDWUNP-YTMVLYRLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.90532504 MHz, C2D6OS, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.0830004 MHz, C2D6OS, 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

Not Available

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	4.81	ChemAxon
pKa (Strongest Acidic)	9.81	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	95.97 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	139.02 m³·mol⁻¹	ChemAxon
Polarizability	51.64 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for giluterrin (NP0332304)

MOL for NP0332304 (giluterrin)

3D MOL for NP0332304 (giluterrin)

3D SDF for NP0332304 (giluterrin)

3D-SDF for NP0332304 (giluterrin)

PDB for NP0332304 (giluterrin)

3D PDB for NP0332304 (giluterrin)

SMILES for NP0332304 (giluterrin)

INCHI for NP0332304 (giluterrin)

Structure for NP0332304 (giluterrin)

3D Structure for NP0332304 (giluterrin)