NP-MRD: Showing NP-Card for (4r,7r)-n-[(2r,5s,8s,8as)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5h,8h-[1,3]oxazolo[3,2-a]pyrazin-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 (NP0330337)

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Record Information

Version

1.0

Created at

2022-09-12 15:35:08 UTC

Updated at

2022-09-12 15:35:08 UTC

NP-MRD ID

NP0330337

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r,7r)-n-[(2r,5s,8s,8as)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5h,8h-[1,3]oxazolo[3,2-a]pyrazin-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

Ergobalansine belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. (4r,7r)-n-[(2r,5s,8s,8as)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5h,8h-[1,3]oxazolo[3,2-a]pyrazin-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 Balansia cyperi. It was first documented in 2013 (PMID: 23835852). Based on a literature review a significant number of articles have been published on Ergobalansine (PMID: 36130844) (PMID: 36130843) (PMID: 36130842) (PMID: 36130841) (PMID: 36130840) (PMID: 36130836).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122217352D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309122217352D          

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    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
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  4  0  0  0
 19 17  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  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  2  0  0  0  0
 26 27  1  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
 22 30  2  0  0  0  0
 26 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 19 35  1  0  0  0  0
 14 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
  5 38  1  0  0  0  0
 11 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330337

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@@H]1N2C(=O)[C@@](C)(O[C@@]2(O)[C@H](C)N=C1O)N=C(O)[C@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H35N5O5/c1-14(2)9-22-25(35)30-15(3)28(37)33(22)26(36)27(4,38-28)31-24(34)17-10-19-18-7-6-8-20-23(18)16(12-29-20)11-21(19)32(5)13-17/h6-8,10,12,14-15,17,21-22,29,37H,9,11,13H2,1-5H3,(H,30,35)(H,31,34)/t15-,17+,21+,22-,27+,28-/m0/s1

> <INCHI_KEY>
JUCIBGILHVUKSN-NLTYGUFLSA-N

> <FORMULA>
C28H35N5O5

> <MOLECULAR_WEIGHT>
521.618

> <EXACT_MASS>
521.263819247

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
56.40289494987876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,7R)-N-[(2R,5S,8S,8aS)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-2H,3H,5H,8H,8aH-[1,3]oxazolo[3,2-a]pyrazin-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_LOGP>
0.6847885960865745

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
4.752140131276226

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.111001208898259

> <JCHEM_PKA_STRONGEST_BASIC>
8.085878622013086

> <JCHEM_POLAR_SURFACE_AREA>
133.98000000000002

> <JCHEM_REFRACTIVITY>
142.57670000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4R,7R)-N-[(2R,5S,8S,8aS)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5H,8H-[1,3]oxazolo[3,2-a]pyrazin-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                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       6.552  -9.536   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.017  -9.060   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.161 -10.091   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.337  -7.554   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.802  -7.078   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.946  -8.109   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.626  -9.615   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      12.411  -7.633   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      12.731  -6.126   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.195  -5.650   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.586  -5.096   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.993  -4.470   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      11.586  -3.556   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.748  -1.673   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       8.788  -2.310   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.122   0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.787  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.944  -2.537   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.479  -3.013   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.335  -1.982   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      -0.250   0.770   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.120  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       6.121   2.310   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.217  -4.326   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       7.677  -4.326   0.000  0.00  0.00           O+0
HETATM   38  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                                                       
CONECT    5    4    6   38                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   38                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16   36                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   35                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   32                                                  
CONECT   22   21   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29   22   26                                                  
CONECT   31   29   32                                                       
CONECT   32   31   21   33                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   19                                                       
CONECT   36   14   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36    5   11                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₅N₅O₅

Average Mass

521.6180 Da

Monoisotopic Mass

521.26382 Da

IUPAC Name

(4R,7R)-N-[(2R,5S,8S,8aS)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-2H,3H,5H,8H,8aH-[1,3]oxazolo[3,2-a]pyrazin-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,7R)-N-[(2R,5S,8S,8aS)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5H,8H-[1,3]oxazolo[3,2-a]pyrazin-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)C[C@@H]1N2C(=O)[C@@](C)(O[C@@]2(O)[C@H](C)N=C1O)N=C(O)[C@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1

InChI Identifier

InChI=1S/C28H35N5O5/c1-14(2)9-22-25(35)30-15(3)28(37)33(22)26(36)27(4,38-28)31-24(34)17-10-19-18-7-6-8-20-23(18)16(12-29-20)11-21(19)32(5)13-17/h6-8,10,12,14-15,17,21-22,29,37H,9,11,13H2,1-5H3,(H,30,35)(H,31,34)/t15-,17+,21+,22-,27+,28-/m0/s1

InChI Key

JUCIBGILHVUKSN-NLTYGUFLSA-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
Balansia cyperi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Hybrid peptide
Alpha-dipeptide
Lysergic acid or derivatives
Lysergic acid amide
Indoloquinoline
Ergoline skeleton
Benzoquinoline
Quinoline-3-carboxamide
Pyrroloquinoline
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Alkaloid or derivatives
Aralkylamine
1,4-diazinane
Piperazine
Oxazolidinone
Benzenoid
Tertiary carboxylic acid amide
Heteroaromatic compound
Pyrrole
Oxazolidine
Tertiary amine
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Tertiary aliphatic amine
Lactam
Orthocarboxylic acid derivative
Oxacycle
Carboxylic acid derivative
Azacycle
Alkanolamine
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Carbonyl group
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	0.68	ChemAxon
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	8.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	142.58 m³·mol⁻¹	ChemAxon
Polarizability	56.4 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	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

58828627

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14753572

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cani I, Righini M, Cenni P, Foschi M: Teaching NeuroImage: Partially Reversible Widespread Leukoencephalopathy Associated With Atypical Hemolytic Uremic Syndrome. Neurology. 2022 Sep 21. pii: WNL.0000000000201378. doi: 10.1212/WNL.0000000000201378. [PubMed:36130844 ]
Sasaki R, Morimoto S, Ozawa F, Okano H, Yoshida M, Ishiura H, Tsuji S, Kuzuhara S, Kokubo Y: APOE Alleles With Tau and Abeta Pathology In Patients With Amyotrophic Lateral Sclerosis and Parkinsonism-Dementia Complex in the Kii Peninsula. Neurology. 2022 Sep 21. pii: WNL.0000000000201156. doi: 10.1212/WNL.0000000000201156. [PubMed:36130843 ]
Zhang Z, Wang M, Gill D, Liu X: Genetically Predicted Smoking and Alcohol Consumption and Functional Outcome After Ischemic Stroke. Neurology. 2022 Sep 21. pii: WNL.0000000000201291. doi: 10.1212/WNL.0000000000201291. [PubMed:36130842 ]
Khamis S, Mitakidou MR, Champion M, Goyal S, Jones RL, Siddiqui A, Sabanathan S, Hedderly T, Lin JP, Jungbluth H, Papandreou A: Clinical Reasoning: A Teenage Girl With Progressive Hyperkinetic Movements, Seizures, and Encephalopathy. Neurology. 2022 Sep 21. pii: WNL.0000000000201385. doi: 10.1212/WNL.0000000000201385. [PubMed:36130841 ]
Rosenberg A, Ohlund-Wistbacka U, Hall A, Bonnard A, Hagman G, Ryden M, Thunborg C, Wiggenraad F, Sandebring-Matton A, Solomon A, Kivipelto M: beta-Amyloid, Tau, Neurodegeneration Classification and Eligibility for Anti-amyloid Treatment in a Memory Clinic Population. Neurology. 2022 Sep 21. pii: WNL.0000000000201043. doi: 10.1212/WNL.0000000000201043. [PubMed:36130840 ]
Yu H, Cai G, Wu J, Li Q: Clinical Phenotypic Variability and Significance of Pneumolabyrinth After Tympanum-Penetrating Injury. Ear Nose Throat J. 2022 Sep 21:1455613221128132. doi: 10.1177/01455613221128132. [PubMed:36130836 ]
Beaulieu WT, Panaccione DG, Hazekamp CS, mckee MC, Ryan KL, Clay K: Differential allocation of seed-borne ergot alkaloids during early ontogeny of morning glories (Convolvulaceae). J Chem Ecol. 2013 Jul;39(7):919-30. doi: 10.1007/s10886-013-0314-z. Epub 2013 Jul 9. [PubMed:23835852 ]
Silverman A, Beres S: Child Neurology: Horner Syndrome in an Otherwise Well-Appearing Infant. Neurology. 2022 Sep 21. pii: WNL.0000000000201377. doi: 10.1212/WNL.0000000000201377. [PubMed:36130839 ]
Harada Y, Wang SH, Juel VC: Clinical Reasoning: A 36-Year-Old Man With Asymmetric Muscle Weakness. Neurology. 2022 Sep 21. pii: WNL.0000000000201379. doi: 10.1212/WNL.0000000000201379. [PubMed:36130838 ]
Guest O, Memon AA, Chukweubuka A, Zaheer M, Siddiqi N: Robotic low anterior resection for locally advanced rectal cancer - A video vignette. Colorectal Dis. 2022 Sep 21. doi: 10.1111/codi.16345. [PubMed:36130837 ]
LOTUS database [Link]

Showing NP-Card for (4r,7r)-n-[(2r,5s,8s,8as)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5h,8h-[1,3]oxazolo[3,2-a]pyrazin-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 (NP0330337)

MOL for NP0330337 ((4r,7r)-n-[(2r,5s,8s,8as)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5h,8h-[1,3]oxazolo[3,2-a]pyrazin-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 NP0330337 ((4r,7r)-n-[(2r,5s,8s,8as)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5h,8h-[1,3]oxazolo[3,2-a]pyrazin-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 NP0330337 ((4r,7r)-n-[(2r,5s,8s,8as)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5h,8h-[1,3]oxazolo[3,2-a]pyrazin-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 NP0330337 ((4r,7r)-n-[(2r,5s,8s,8as)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5h,8h-[1,3]oxazolo[3,2-a]pyrazin-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 NP0330337 ((4r,7r)-n-[(2r,5s,8s,8as)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5h,8h-[1,3]oxazolo[3,2-a]pyrazin-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 NP0330337 ((4r,7r)-n-[(2r,5s,8s,8as)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5h,8h-[1,3]oxazolo[3,2-a]pyrazin-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 NP0330337 ((4r,7r)-n-[(2r,5s,8s,8as)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5h,8h-[1,3]oxazolo[3,2-a]pyrazin-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 NP0330337 ((4r,7r)-n-[(2r,5s,8s,8as)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5h,8h-[1,3]oxazolo[3,2-a]pyrazin-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 NP0330337 ((4r,7r)-n-[(2r,5s,8s,8as)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5h,8h-[1,3]oxazolo[3,2-a]pyrazin-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 NP0330337 ((4r,7r)-n-[(2r,5s,8s,8as)-6,8a-dihydroxy-2,8-dimethyl-5-(2-methylpropyl)-3-oxo-5h,8h-[1,3]oxazolo[3,2-a]pyrazin-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)