NP-MRD: Showing NP-Card for (4r)-n-[(2r,3r)-1-[(3s,8ar)-3-[(2s)-butan-2-yl]-1,4-dioxo-tetrahydro-3h-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid (NP0159516)

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Record Information

Version

2.0

Created at

2022-09-02 17:16:56 UTC

Updated at

2022-09-02 17:16:56 UTC

NP-MRD ID

NP0159516

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r)-n-[(2r,3r)-1-[(3s,8ar)-3-[(2s)-butan-2-yl]-1,4-dioxo-tetrahydro-3h-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid

Description

Ss,ss-ergoannam belongs to the class of organic compounds known as ergopeptams. These are tripeptidic noncyclol ergot alkaloids. The structure of ergopeptams is similar to ergopeptines except that L-proline is exchanged by D-proline, and the tripeptide chain is a noncyclol lactam. (4r)-n-[(2r,3r)-1-[(3s,8ar)-3-[(2s)-butan-2-yl]-1,4-dioxo-tetrahydro-3h-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid is found in Claviceps purpurea. Based on a literature review very few articles have been published on ss,ss-ergoannam.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022219162D          

 42 47  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022219162D          

 42 47  0  0  1  0            999 V2000
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    2.4943   -2.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771   -1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -1.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12  8  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 20 21  1  4  0  0  0
 22 20  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 25 33  2  0  0  0  0
 29 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 24 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 22 38  1  0  0  0  0
 18 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159516

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)[C@@H](N=C(O)[C@H]1CN(C)C2CC3=CNC4=CC=CC(=C34)C2=C1)C(=O)N1[C@@H]([C@@H](C)CC)C(=O)N2CCC[C@@H]2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H43N5O4/c1-6-18(3)28(32(41)38-29(19(4)7-2)33(42)37-13-9-12-25(37)31(38)40)35-30(39)21-14-23-22-10-8-11-24-27(22)20(16-34-24)15-26(23)36(5)17-21/h8,10-11,14,16,18-19,21,25-26,28-29,34H,6-7,9,12-13,15,17H2,1-5H3,(H,35,39)/t18-,19+,21-,25-,26?,28-,29+/m1/s1

> <INCHI_KEY>
IHDIXBZKTTXKMY-ADKHCRFMSA-N

> <FORMULA>
C33H43N5O4

> <MOLECULAR_WEIGHT>
573.738

> <EXACT_MASS>
573.331504885

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
61.803662284911

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R)-N-[(2R,3R)-1-[(3S,8aR)-3-[(2S)-butan-2-yl]-1,4-dioxo-octahydropyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
1.7076960499693252

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.241245983350613

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.7230900825427655

> <JCHEM_PKA_STRONGEST_BASIC>
8.271776992237074

> <JCHEM_POLAR_SURFACE_AREA>
109.31000000000002

> <JCHEM_REFRACTIVITY>
161.84030000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-N-[(2R,3R)-1-[(3S,8aR)-3-[(2S)-butan-2-yl]-1,4-dioxo-tetrahydro-3H-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      12.789  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.455  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.122  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.122  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.788  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454  -7.700   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.454  -9.240   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       6.121  -6.930   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.656  -7.406   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.751  -6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.656  -4.914   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.121  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.454  -3.080   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       8.788  -5.390   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.455  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       8.788  -2.310   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.122   0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.787  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.944  -2.537   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.479  -3.013   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.335  -1.982   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      -0.250   0.770   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.120  -0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       6.121   2.310   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.789  -3.080   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.455  -0.770   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      12.789   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   15                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    5   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   39                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   38                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   35                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32   25   29                                                  
CONECT   34   32   35                                                       
CONECT   35   34   24   36                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   22                                                       
CONECT   39   18   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₃N₅O₄

Average Mass

573.7380 Da

Monoisotopic Mass

573.33150 Da

IUPAC Name

(4R)-N-[(2R,3R)-1-[(3S,8aR)-3-[(2S)-butan-2-yl]-1,4-dioxo-octahydropyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid

Traditional Name

(4R)-N-[(2R,3R)-1-[(3S,8aR)-3-[(2S)-butan-2-yl]-1,4-dioxo-tetrahydro-3H-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)[C@@H](N=C(O)[C@H]1CN(C)C2CC3=CNC4=CC=CC(=C34)C2=C1)C(=O)N1[C@@H]([C@@H](C)CC)C(=O)N2CCC[C@@H]2C1=O

InChI Identifier

InChI=1S/C33H43N5O4/c1-6-18(3)28(32(41)38-29(19(4)7-2)33(42)37-13-9-12-25(37)31(38)40)35-30(39)21-14-23-22-10-8-11-24-27(22)20(16-34-24)15-26(23)36(5)17-21/h8,10-11,14,16,18-19,21,25-26,28-29,34H,6-7,9,12-13,15,17H2,1-5H3,(H,35,39)/t18-,19+,21-,25-,26?,28-,29+/m1/s1

InChI Key

IHDIXBZKTTXKMY-ADKHCRFMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Claviceps purpurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergopeptams. These are tripeptidic noncyclol ergot alkaloids. The structure of ergopeptams is similar to ergopeptines except that L-proline is exchanged by D-proline, and the tripeptide chain is a noncyclol lactam.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Lysergic acids and derivatives

Direct Parent

Ergopeptams

Alternative Parents

Substituents

Ergopeptam-skeleton
Hybrid peptide
Alpha-dipeptide
Lysergic acid amide
Indoloquinoline
Isoleucine or derivatives
Benzoquinoline
Quinoline-3-carboxamide
N-acyl-alpha amino acid or derivatives
Pyrroloquinoline
Alpha-amino acid amide
Alpha-amino acid or derivatives
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Dioxopiperazine
2,5-dioxopiperazine
Aralkylamine
N-alkylpiperazine
1,4-diazinane
Benzenoid
Carboxylic acid imide, n-substituted
Piperazine
Tertiary carboxylic acid amide
Carboxylic acid imide
Dicarboximide
Heteroaromatic compound
Pyrrolidine
Pyrrole
Tertiary aliphatic amine
Amino acid or derivatives
Lactam
Carboxamide group
Tertiary amine
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Organooxygen compound
Amine
Organic nitrogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organonitrogen 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	3.81	ALOGPS
logP	1.71	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.72	ChemAxon
pKa (Strongest Basic)	8.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.31 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	161.84 m³·mol⁻¹	ChemAxon
Polarizability	61.8 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

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KNApSAcK ID

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Chemspider ID

29212567

KEGG Compound ID

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BioCyc ID

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BiGG ID

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Wikipedia Link

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METLIN ID

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PubChem Compound

139585358

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References

General References

LOTUS database [Link]

Showing NP-Card for (4r)-n-[(2r,3r)-1-[(3s,8ar)-3-[(2s)-butan-2-yl]-1,4-dioxo-tetrahydro-3h-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid (NP0159516)

MOL for NP0159516 ((4r)-n-[(2r,3r)-1-[(3s,8ar)-3-[(2s)-butan-2-yl]-1,4-dioxo-tetrahydro-3h-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

3D MOL for NP0159516 ((4r)-n-[(2r,3r)-1-[(3s,8ar)-3-[(2s)-butan-2-yl]-1,4-dioxo-tetrahydro-3h-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

3D SDF for NP0159516 ((4r)-n-[(2r,3r)-1-[(3s,8ar)-3-[(2s)-butan-2-yl]-1,4-dioxo-tetrahydro-3h-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

3D-SDF for NP0159516 ((4r)-n-[(2r,3r)-1-[(3s,8ar)-3-[(2s)-butan-2-yl]-1,4-dioxo-tetrahydro-3h-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

PDB for NP0159516 ((4r)-n-[(2r,3r)-1-[(3s,8ar)-3-[(2s)-butan-2-yl]-1,4-dioxo-tetrahydro-3h-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

3D PDB for NP0159516 ((4r)-n-[(2r,3r)-1-[(3s,8ar)-3-[(2s)-butan-2-yl]-1,4-dioxo-tetrahydro-3h-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

SMILES for NP0159516 ((4r)-n-[(2r,3r)-1-[(3s,8ar)-3-[(2s)-butan-2-yl]-1,4-dioxo-tetrahydro-3h-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

INCHI for NP0159516 ((4r)-n-[(2r,3r)-1-[(3s,8ar)-3-[(2s)-butan-2-yl]-1,4-dioxo-tetrahydro-3h-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

Structure for NP0159516 ((4r)-n-[(2r,3r)-1-[(3s,8ar)-3-[(2s)-butan-2-yl]-1,4-dioxo-tetrahydro-3h-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

3D Structure for NP0159516 ((4r)-n-[(2r,3r)-1-[(3s,8ar)-3-[(2s)-butan-2-yl]-1,4-dioxo-tetrahydro-3h-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)