NP-MRD: Showing NP-Card for Ergobutine (NP0057962)

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Record Information

Version

2.0

Created at

2022-04-28 03:18:46 UTC

Updated at

2022-04-28 03:18:47 UTC

NP-MRD ID

NP0057962

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ergobutine

Description

(4R,7R)-N-[(1S,2S,4R,7S)-4,7-diethyl-2-hydroxy-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]Dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid belongs to the class of organic compounds known as ergopeptines. These are ergoline derivatives that contain a tripeptide structure attached to the basic ergoline ring in the same location as the amide group of the lysergic acid derivatives. Ergobutine is found in Claviceps purpurea . Based on a literature review very few articles have been published on (4R,7R)-N-[(1S,2S,4R,7S)-4,7-diethyl-2-hydroxy-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]Dodecan-4-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

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205182D          

 39 45  0  0  1  0            999 V2000
    0.1794    1.8869    0.0000 C   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
    1.7486    1.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9934   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  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
    1.1355    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1340    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
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  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
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  9 10  1  0  0  0  0
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  7 12  1  0  0  0  0
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  3 14  1  0  0  0  0
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  2 16  1  0  0  0  0
 11 17  1  0  0  0  0
  9 18  1  1  0  0  0
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 27 36  1  0  0  0  0
 25 37  1  6  0  0  0
 21 38  1  1  0  0  0
 38 39  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282205182D          

 39 45  0  0  1  0            999 V2000
    0.1794    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7762    3.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5284    5.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    5.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5363    5.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6154    3.9814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7579    1.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5784    1.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  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
 12 11  1  6  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 11 17  1  0  0  0  0
  9 18  1  1  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 28 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 27 36  1  0  0  0  0
 25 37  1  6  0  0  0
 21 38  1  1  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057962

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H]1N2C(=O)[C@](CC)(NC(=O)[C@H]3CN(C)[C@@H]4CC5=CNC6=CC=CC(=C56)C4=C3)O[C@@]2(O)[C@@H]2CCCN2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H35N5O5/c1-4-21-26(36)33-11-7-10-23(33)29(38)34(21)27(37)28(5-2,39-29)31-25(35)17-12-19-18-8-6-9-20-24(18)16(14-30-20)13-22(19)32(3)15-17/h6,8-9,12,14,17,21-23,30,38H,4-5,7,10-11,13,15H2,1-3H3,(H,31,35)/t17-,21+,22-,23+,28-,29+/m1/s1

> <INCHI_KEY>
NNUSZQKLCHDFJJ-ZDRNFBCMSA-N

> <FORMULA>
C29H35N5O5

> <MOLECULAR_WEIGHT>
533.629

> <EXACT_MASS>
533.263819247

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
57.21574062969705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,7R)-N-[(1S,2S,4R,7S)-4,7-diethyl-2-hydroxy-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

> <ALOGPS_LOGP>
2.59

> <JCHEM_LOGP>
2.1007827309382328

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.644992298596723

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.695363711895382

> <JCHEM_PKA_STRONGEST_BASIC>
7.780482338824266

> <JCHEM_POLAR_SURFACE_AREA>
118.21

> <JCHEM_REFRACTIVITY>
144.5416

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,7R)-N-[(1S,2S,4R,7S)-4,7-diethyl-2-hydroxy-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       0.335   3.522   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.264   2.570   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.944   4.077   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.479   4.553   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.454  -0.000   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       6.121  -0.770   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -0.250   0.770   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.122   1.540   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       8.788   3.850   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.586   5.096   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.832   4.191   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0      11.586   6.636   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      10.122   7.112   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.217   5.866   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.802   8.618   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      10.946   9.649   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      12.411   9.173   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.555  10.203   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.731   7.666   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.195   7.190   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.516   5.684   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.320  11.055   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.788  10.894   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.468   9.388   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.615   7.432   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.748   3.213   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.280   3.052   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   16                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    2                                                       
CONECT   17   11                                                            
CONECT   18    9   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   26   38                                             
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   31                                                  
CONECT   25   24   26   27   37                                             
CONECT   26   25   21                                                       
CONECT   27   25   28   36                                                  
CONECT   28   27   29   34                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   28   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   27                                                       
CONECT   37   25                                                            
CONECT   38   21   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Value	Source
(4R,7R)-N-[(1S,2S,4R,7S)-4,7-Diethyl-2-hydroxy-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0,]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0,.0,]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidate	Generator

Chemical Formula

C₂₉H₃₅N₅O₅

Average Mass

533.6290 Da

Monoisotopic Mass

533.26382 Da

IUPAC Name

(4R,7R)-N-[(1S,2S,4R,7S)-4,7-diethyl-2-hydroxy-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@@H]1N2C(=O)[C@](CC)(NC(=O)[C@H]3CN(C)[C@@H]4CC5=CNC6=CC=CC(=C56)C4=C3)O[C@@]2(O)[C@@H]2CCCN2C1=O

InChI Identifier

InChI=1S/C29H35N5O5/c1-4-21-26(36)33-11-7-10-23(33)29(38)34(21)27(37)28(5-2,39-29)31-25(35)17-12-19-18-8-6-9-20-24(18)16(14-30-20)13-22(19)32(3)15-17/h6,8-9,12,14,17,21-23,30,38H,4-5,7,10-11,13,15H2,1-3H3,(H,31,35)/t17-,21+,22-,23+,28-,29+/m1/s1

InChI Key

NNUSZQKLCHDFJJ-ZDRNFBCMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergopeptines. These are ergoline derivatives that contain a tripeptide structure attached to the basic ergoline ring in the same location as the amide group of the lysergic acid derivatives.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Lysergic acids and derivatives

Direct Parent

Ergopeptines

Alternative Parents

Substituents

Hybrid peptide
Ergopeptine
Alpha-dipeptide
Lysergic acid amide
Indoloquinoline
Benzoquinoline
Quinoline-3-carboxamide
N-acyl-alpha amino acid or derivatives
Pyrroloquinoline
Quinoline
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
N-alkylpiperazine
1,4-diazinane
Benzenoid
Oxazolidinone
Piperazine
Pyrrolidine
Pyrrole
Heteroaromatic compound
Tertiary carboxylic acid amide
Oxazolidine
Carboxamide group
Amino acid or derivatives
Lactam
Tertiary aliphatic amine
Tertiary amine
Orthocarboxylic acid derivative
Secondary carboxylic acid amide
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Azacycle
Alkanolamine
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
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	2.59	ALOGPS
logP	2.1	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.7	ChemAxon
pKa (Strongest Basic)	7.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	118.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	144.54 m³·mol⁻¹	ChemAxon
Polarizability	57.22 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

19988478

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21123645

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ergobutine (NP0057962)

MOL for NP0057962 (Ergobutine)

3D MOL for NP0057962 (Ergobutine)

3D SDF for NP0057962 (Ergobutine)

3D-SDF for NP0057962 (Ergobutine)

PDB for NP0057962 (Ergobutine)

3D PDB for NP0057962 (Ergobutine)

SMILES for NP0057962 (Ergobutine)

INCHI for NP0057962 (Ergobutine)

Structure for NP0057962 (Ergobutine)

3D Structure for NP0057962 (Ergobutine)