NP-MRD: Showing NP-Card for Glandicoline B (NP0332842)

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Record Information

Version

2.0

Created at

2024-04-25 18:45:09 UTC

Updated at

2024-09-03 04:20:27 UTC

NP-MRD ID

NP0332842

Natural Product DOI

https://doi.org/10.57994/2117

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glandicoline B

Description

Glandicoline B was first documented in 2013 (PMID: 23776469). Based on a literature review a significant number of articles have been published on glandicoline B (PMID: 26668029) (PMID: 30141817) (PMID: 25998659) (PMID: 31414824) (PMID: 32166015).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01072321222D          

 31 35  0  0  1  0            999 V2000
    4.6296   -0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8450   -1.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3601   -1.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5124   -1.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4262   -2.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1776   -0.5520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0060   -1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2214   -1.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6083   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8237   -1.3168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    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
    2.5645    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7631    1.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9346    2.0202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201    2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930    1.8806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000    0.7537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7205    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3336    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1182    0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2897    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6766   -0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8920   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4875    1.4681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0499   -2.4209    0.0000 O   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
  4  5  2  0  0  0  0
  6  2  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  1  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 18 22  1  0  0  0  0
 12 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  2  0  0  0  0
  6 29  1  0  0  0  0
 24 29  1  0  0  0  0
 23 30  1  0  0  0  0
  8 31  1  0  0  0  0
M  END


  Mrv2104 01072321222D          

 31 35  0  0  1  0            999 V2000
    4.6296   -0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8450   -1.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3601   -1.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5124   -1.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4262   -2.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1776   -0.5520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0060   -1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2214   -1.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6083   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8237   -1.3168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    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
    2.5645    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7631    1.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9346    2.0202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201    2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930    1.8806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000    0.7537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7205    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3336    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1182    0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2897    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6766   -0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8920   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4875    1.4681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0499   -2.4209    0.0000 O   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
  4  5  2  0  0  0  0
  6  2  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  1  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 18 22  1  0  0  0  0
 12 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  2  0  0  0  0
  6 29  1  0  0  0  0
 24 29  1  0  0  0  0
 23 30  1  0  0  0  0
  8 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332842

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C=C)[C@]12C=C(O)C(=O)N3\C(=C\C4=CN=CN4)C(=O)N[C@]13N(O)C1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C22H21N5O4/c1-4-20(2,3)21-10-17(28)19(30)26-16(9-13-11-23-12-24-13)18(29)25-22(21,26)27(31)15-8-6-5-7-14(15)21/h4-12,28,31H,1H2,2-3H3,(H,23,24)(H,25,29)/b16-9+/t21-,22-/m1/s1

> <INCHI_KEY>
YEVSOYBNHBOQJZ-GCTRCSCRSA-N

> <FORMULA>
C22H21N5O4

> <MOLECULAR_WEIGHT>
419.441

> <EXACT_MASS>
419.159354176

$$$$

HEADER    PROTEIN                                 07-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-23         0                                  
HETATM    1  C   UNK     0       8.642  -1.460   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.177  -1.936   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.272  -3.182   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.423  -2.841   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.262  -4.372   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.931  -1.030   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.611  -2.537   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.147  -3.013   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.002  -1.982   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.538  -2.458   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       3.322  -0.476   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  N   UNK     0       4.787   1.540   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.877   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.107   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.424   2.265   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -1.745   3.771   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -0.411   4.541   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       0.734   3.511   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       5.413   1.407   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       6.945   1.246   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.089   2.276   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.554   1.800   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.874   0.294   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.730  -0.736   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.265  -0.260   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.643   2.741   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       3.826  -4.519   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    6                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7   12   29                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11    6   13   23                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   11   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   18                                                       
CONECT   23   12   24   30                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    6   24                                                  
CONECT   30   23                                                            
CONECT   31    8                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₁N₅O₄

Average Mass

419.4410 Da

Monoisotopic Mass

419.15935 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)[C@]12C=C(O)C(=O)N3\C(=C\C4=CN=CN4)C(=O)N[C@]13N(O)C1=CC=CC=C21

InChI Identifier

InChI=1S/C22H21N5O4/c1-4-20(2,3)21-10-17(28)19(30)26-16(9-13-11-23-12-24-13)18(29)25-22(21,26)27(31)15-8-6-5-7-14(15)21/h4-12,28,31H,1H2,2-3H3,(H,23,24)(H,25,29)/b16-9+/t21-,22-/m1/s1

InChI Key

YEVSOYBNHBOQJZ-GCTRCSCRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	moysesaraujo@ufam.edu.br	Federal University of Amazonas	Moysés Batista de Araújo Júnior	2024-04-25	View Spectrum
1D NMR	²H NMR Spectrum (1D, 61 MHz, CD3OD, experimental)	moysesaraujo@ufam.edu.br	Federal University of Amazonas	Moysés Batista de Araújo Júnior	2024-04-25	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	moysesaraujo@ufam.edu.br	Federal University of Amazonas	Moysés Batista de Araújo Júnior	2024-04-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	moysesaraujo@ufam.edu.br	Federal University of Amazonas	Moysés Batista de Araújo Júnior	2024-04-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	moysesaraujo@ufam.edu.br	Federal University of Amazonas	Moysés Batista de Araújo Júnior	2024-04-25	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	moysesaraujo@ufam.edu.br	Federal University of Amazonas	Moysés Batista de Araújo Júnior	2024-04-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	moysesaraujo@ufam.edu.br	Federal University of Amazonas	Moysés Batista de Araújo Júnior	2024-04-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	moysesaraujo@ufam.edu.br	Federal University of Amazonas	Moysés Batista de Araújo Júnior	2024-04-25	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
sp.		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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00052003

Chemspider ID

64808353

KEGG Compound ID

Not Available

BioCyc ID

CPD-17390

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124079399

PDB ID

Not Available

ChEBI ID

134347

Good Scents ID

Not Available

References

General References

Martin JF, Liras P: Evolutionary formation of gene clusters by reorganization: the meleagrin/roquefortine paradigm in different fungi. Appl Microbiol Biotechnol. 2016 Feb;100(4):1579-1587. doi: 10.1007/s00253-015-7192-y. Epub 2015 Dec 15. [PubMed:26668029 ]
Newmister SA, Romminger S, Schmidt JJ, Williams RM, Smith JL, Berlinck RGS, Sherman DH: Unveiling sequential late-stage methyltransferase reactions in the meleagrin/oxaline biosynthetic pathway. Org Biomol Chem. 2018 Sep 11;16(35):6450-6459. doi: 10.1039/c8ob01565a. [PubMed:30141817 ]
Kosalkova K, Dominguez-Santos R, Coton M, Coton E, Garcia-Estrada C, Liras P, Martin JF: A natural short pathway synthesizes roquefortine C but not meleagrin in three different Penicillium roqueforti strains. Appl Microbiol Biotechnol. 2015 Sep;99(18):7601-12. doi: 10.1007/s00253-015-6676-0. Epub 2015 May 22. [PubMed:25998659 ]
Yan Q, Carroll PJ, Gau MR, Winkler JD, Joullie MM: A Transannular Rearrangement Reaction of a Pyrroloindoline Diketopiperazine. Org Lett. 2019 Sep 6;21(17):6619-6623. doi: 10.1021/acs.orglett.9b02084. Epub 2019 Aug 15. [PubMed:31414824 ]
Ali H, Ries MI, Nijland JG, Lankhorst PP, Hankemeier T, Bovenberg RA, Vreeken RJ, Driessen AJ: A branched biosynthetic pathway is involved in production of roquefortine and related compounds in Penicillium chrysogenum. PLoS One. 2013 Jun 12;8(6):e65328. doi: 10.1371/journal.pone.0065328. Print 2013. [PubMed:23776469 ]
Saygin D, Tabib T, Bittar HET, Valenzi E, Sembrat J, Chan SY, Rojas M, Lafyatis R: Transcriptional profiling of lung cell populations in idiopathic pulmonary arterial hypertension. Pulm Circ. 2020 Feb 28;10(1):???. doi: 10.1177/2045894020908782. eCollection 2020 Jan-Mar. [PubMed:32166015 ]

Showing NP-Card for Glandicoline B (NP0332842)

MOL for NP0332842 (Glandicoline B)

3D MOL for NP0332842 (Glandicoline B)

3D SDF for NP0332842 (Glandicoline B)

3D-SDF for NP0332842 (Glandicoline B)

PDB for NP0332842 (Glandicoline B)

3D PDB for NP0332842 (Glandicoline B)

SMILES for NP0332842 (Glandicoline B)

INCHI for NP0332842 (Glandicoline B)

Structure for NP0332842 (Glandicoline B)

3D Structure for NP0332842 (Glandicoline B)