NP-MRD: Showing NP-Card for (4s,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-isopropyl-4-methyl-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 (NP0145767)

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Record Information

Version

2.0

Created at

2022-09-02 01:02:02 UTC

Updated at

2022-09-02 01:02:02 UTC

NP-MRD ID

NP0145767

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-isopropyl-4-methyl-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

Description

Ergovalinine 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. (4s,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-isopropyl-4-methyl-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 is found in Cenchrus echinatus, Epichloe typhina and Festuca rubra. (4s,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-isopropyl-4-methyl-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 was first documented in 2019 (PMID: 30957833). Based on a literature review a small amount of articles have been published on Ergovalinine (PMID: 35947831) (PMID: 33287449) (PMID: 33053893) (PMID: 30895321).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022203022D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309022203022D          

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    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  1  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
    4.9374   -2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.9849    0.0000 N   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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  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
 10 11  1  0  0  0  0
 11  7  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  4  0  0  0
 20 18  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  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  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 23 31  2  0  0  0  0
 27 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 22 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 20 36  1  0  0  0  0
 15 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
  4 39  1  0  0  0  0
 12 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0145767

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1N2C(=O)[C@@](C)(O[C@@]2(O)[C@@H]2CCCN2C1=O)N=C(O)[C@@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H35N5O5/c1-15(2)24-26(36)33-10-6-9-22(33)29(38)34(24)27(37)28(3,39-29)31-25(35)17-11-19-18-7-5-8-20-23(18)16(13-30-20)12-21(19)32(4)14-17/h5,7-8,11,13,15,17,21-22,24,30,38H,6,9-10,12,14H2,1-4H3,(H,31,35)/t17-,21+,22-,24-,28+,29-/m0/s1

> <INCHI_KEY>
BGHDUTQZGWOQIA-KPUJGURZSA-N

> <FORMULA>
C29H35N5O5

> <MOLECULAR_WEIGHT>
533.629

> <EXACT_MASS>
533.263819247

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
56.24011405295998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,7R)-N-[(1S,2S,4R,7S)-2-hydroxy-4-methyl-5,8-dioxo-7-(propan-2-yl)-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-carboximidic acid

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
0.15275993688857667

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.718608418247822

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.436351762407942

> <JCHEM_PKA_STRONGEST_BASIC>
8.084297188215505

> <JCHEM_POLAR_SURFACE_AREA>
121.7

> <JCHEM_REFRACTIVITY>
145.0661

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,7R)-N-[(1S,2S,4R,7S)-2-hydroxy-7-isopropyl-4-methyl-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-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       8.017  -9.060   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.337  -7.554   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.192  -6.524   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.802  -7.078   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.946  -8.109   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.626  -9.615   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      12.411  -7.633   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      13.744  -8.403   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.889  -7.372   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.262  -5.965   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.731  -6.126   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.586  -5.096   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.993  -4.470   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      11.586  -3.556   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.748  -1.673   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       8.788  -2.310   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.122   0.000   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.787  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.944  -2.537   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.479  -3.013   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.335  -1.982   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      -0.250   0.770   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.120  -0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       6.121   2.310   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.217  -4.326   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       7.677  -4.326   0.000  0.00  0.00           O+0
HETATM   39  N   UNK     0      10.122  -5.572   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   39                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7   12                                                  
CONECT   12   11   13   14   39                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   37                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   36                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   33                                                  
CONECT   23   22   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30   23   27                                                  
CONECT   32   30   33                                                       
CONECT   33   32   22   34                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   20                                                       
CONECT   37   15   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    4   12                                                  
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₅N₅O₅

Average Mass

533.6290 Da

Monoisotopic Mass

533.26382 Da

IUPAC Name

(4S,7R)-N-[(1S,2S,4R,7S)-2-hydroxy-4-methyl-5,8-dioxo-7-(propan-2-yl)-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-carboximidic acid

Traditional Name

(4S,7R)-N-[(1S,2S,4R,7S)-2-hydroxy-7-isopropyl-4-methyl-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-carboximidic acid

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1N2C(=O)[C@@](C)(O[C@@]2(O)[C@@H]2CCCN2C1=O)N=C(O)[C@@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1

InChI Identifier

InChI=1S/C29H35N5O5/c1-15(2)24-26(36)33-10-6-9-22(33)29(38)34(24)27(37)28(3,39-29)31-25(35)17-11-19-18-7-5-8-20-23(18)16(13-30-20)12-21(19)32(4)14-17/h5,7-8,11,13,15,17,21-22,24,30,38H,6,9-10,12,14H2,1-4H3,(H,31,35)/t17-,21+,22-,24-,28+,29-/m0/s1

InChI Key

BGHDUTQZGWOQIA-KPUJGURZSA-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
Cenchrus echinatus	LOTUS Database	35616633
Epichloe typhina	LOTUS Database	35616633
Festuca rubra	LOTUS Database	35616633

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
Pyrroloquinoline
N-acyl-alpha amino acid or derivatives
3-alkylindole
Quinoline
Alpha-amino acid or derivatives
Isoindole or derivatives
Indole or derivatives
Indole
Aralkylamine
N-alkylpiperazine
Benzenoid
Piperazine
Oxazolidinone
1,4-diazinane
Heteroaromatic compound
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Oxazolidine
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Orthocarboxylic acid derivative
Lactam
Carboxamide group
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	2.37	ALOGPS
logP	0.15	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.44	ChemAxon
pKa (Strongest Basic)	8.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.7 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	145.07 m³·mol⁻¹	ChemAxon
Polarizability	56.24 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

20147835

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20841588

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Britt JL, Greene MA, Klotz JL, Justice SM, Powell RR, Noorai RE, Bruce TF, Duckett SK: Mycotoxin ingestion during late gestation alters placentome structure, cotyledon transcriptome, and fetal development in pregnant sheep. Hum Exp Toxicol. 2022 Jan-Dec;41:9603271221119177. doi: 10.1177/09603271221119177. [PubMed:35947831 ]
Britt JL, Greene MA, Wilbanks SA, Bertrand JK, Klotz JL, Bridges W Jr, Aiken G, Andrae JG, Duckett SK: Feeding Tall Fescue Seed Reduces Ewe Milk Production, Lamb Birth Weight and Pre-Weaning Growth Rate. Animals (Basel). 2020 Dec 3;10(12):2291. doi: 10.3390/ani10122291. [PubMed:33287449 ]
Greene MA, Britt JL, Bertrand JK, Klotz JL, Bridges W Jr, Andrae JG, Duckett SK: Feeding Tall Fescue Seed during Mid and Late Gestation Influences Subsequent Postnatal Growth, Puberty, and Carcass Quality of Offspring. Animals (Basel). 2020 Oct 12;10(10):1859. doi: 10.3390/ani10101859. [PubMed:33053893 ]
Jia Y, Son K, Burris WR, Bridges PJ, Matthews JC: Forms of selenium in vitamin-mineral mixes differentially affect serum alkaline phosphatase activity, and serum albumin and blood urea nitrogen concentrations, of steers grazing endophyte-infected tall fescue. J Anim Sci. 2019 May 30;97(6):2569-2582. doi: 10.1093/jas/skz109. [PubMed:30957833 ]
Britt JL, Greene MA, Bridges WC, Klotz JL, Aiken GE, Andrae JG, Pratt SL, Long NM, Schrick FN, Strickland JR, Wilbanks SA, Miller MF, Koch BM, Duckett SK: Ergot alkaloid exposure during gestation alters. I. Maternal characteristics and placental development of pregnant ewes1. J Anim Sci. 2019 Apr 3;97(4):1874-1890. doi: 10.1093/jas/skz068. [PubMed:30895321 ]
LOTUS database [Link]

Showing NP-Card for (4s,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-isopropyl-4-methyl-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 (NP0145767)

MOL for NP0145767 ((4s,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-isopropyl-4-methyl-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)

3D MOL for NP0145767 ((4s,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-isopropyl-4-methyl-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)

3D SDF for NP0145767 ((4s,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-isopropyl-4-methyl-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)

3D-SDF for NP0145767 ((4s,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-isopropyl-4-methyl-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)

PDB for NP0145767 ((4s,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-isopropyl-4-methyl-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)

3D PDB for NP0145767 ((4s,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-isopropyl-4-methyl-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)

SMILES for NP0145767 ((4s,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-isopropyl-4-methyl-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)

INCHI for NP0145767 ((4s,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-isopropyl-4-methyl-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 for NP0145767 ((4s,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-isopropyl-4-methyl-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)

3D Structure for NP0145767 ((4s,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-isopropyl-4-methyl-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)