NP-MRD: Showing NP-Card for Bostrycin (NP0141128)

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Record Information

Version

1.0

Created at

2022-06-29 22:12:23 UTC

Updated at

2022-06-29 22:12:23 UTC

NP-MRD ID

NP0141128

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bostrycin

Description

Bostrycin belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. It was first documented in 2020 (PMID: 32536871). Based on a literature review a significant number of articles have been published on Bostrycin (PMID: 35205922) (PMID: 34698886) (PMID: 33058154) (PMID: 35117759).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    6.5888    0.4571    0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3454    1.0390    0.6353 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512    0.4431    0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1494   -0.6329   -0.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8864   -1.2523   -0.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9070   -2.2675   -1.5798 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209   -0.6933   -0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3908   -1.2656   -0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4759   -2.3956   -1.5505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7932   -0.7360   -0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7896    0.3808    0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4172    0.9836    0.8377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4233    2.1164    1.6374 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5971    0.4337    0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8935    1.0131    0.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042    2.0284    1.4535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0242    1.0418    1.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749    0.4273    0.4715 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3641    1.4865    0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7709   -0.5601    1.3433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0799   -0.2354   -0.8730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3086   -0.6935   -1.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0686   -1.3557   -0.6960 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5102   -2.2939    0.2331 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7173   -0.5473    0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3844    1.1555    0.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6686    0.4893   -0.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1083   -1.0510   -0.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3405   -2.8888   -1.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4350    2.5062    1.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9899    1.0721    2.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0180    2.1182    0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1685    0.9968   -0.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739    2.2783   -0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6770    1.8562    1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7395   -0.4464    1.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6178    0.4972   -1.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2690   -1.1280   -2.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0586   -1.8755   -1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4581   -2.5018    0.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  1
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 15  3  1  0
 14  7  1  0
 23 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  9 29  1  0
 17 31  1  0
 17 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  6
 22 38  1  0
 23 39  1  6
 24 40  1  0
 13 30  1  0
M  END


  Mrv1652306302200122D          

 24 26  0  0  1  0            999 V2000
    5.0993    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690    1.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  6  9  1  6  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  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
 11 18  1  0  0  0  0
 18 19  2  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 23  1  0  0  0  0
  2 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0141128

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C2=C(O)C3=C(C[C@](C)(O)[C@H](O)[C@@H]3O)C(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O8/c1-16(23)4-5-8(14(21)15(16)22)13(20)9-6(17)3-7(24-2)12(19)10(9)11(5)18/h3,14-15,18,20-23H,4H2,1-2H3/t14-,15-,16+/m1/s1

> <INCHI_KEY>
ZQNOLGRKZRDRQO-OAGGEKHMSA-N

> <FORMULA>
C16H16O8

> <MOLECULAR_WEIGHT>
336.296

> <EXACT_MASS>
336.084517475

$$$$

HEADER    PROTEIN                                 30-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-22         0                                  
HETATM    1  C   UNK     0       9.519   1.273   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.529   2.987   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   24                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    6                                                            
CONECT   10    5   11   23                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11   19                                                  
CONECT   19   18    4   20                                                  
CONECT   20   19                                                            
CONECT   21   15   22                                                       
CONECT   22   21                                                            
CONECT   23   10                                                            
CONECT   24    2                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₈

Average Mass

336.2960 Da

Monoisotopic Mass

336.08452 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C2=C(O)C3=C(C[C@](C)(O)[C@H](O)[C@@H]3O)C(O)=C2C1=O

InChI Identifier

InChI=1S/C16H16O8/c1-16(23)4-5-8(14(21)15(16)22)13(20)9-6(17)3-7(24-2)12(19)10(9)11(5)18/h3,14-15,18,20-23H,4H2,1-2H3/t14-,15-,16+/m1/s1

InChI Key

ZQNOLGRKZRDRQO-OAGGEKHMSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anthraquinone
1,4-anthraquinone
Tetralin
Quinone
Aryl ketone
Vinylogous ester
Vinylogous acid
Tertiary alcohol
Ketone
Secondary alcohol
Polyol
Organooxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00048582

Chemspider ID

28612

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

30839

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang H, Guo Y, Luo Z, Gao L, Li R, Zhang Y, Kalaji HM, Qiang S, Chen S: Recent Advances in Alternaria Phytotoxins: A Review of Their Occurrence, Structure, Bioactivity, and Biosynthesis. J Fungi (Basel). 2022 Feb 9;8(2):168. doi: 10.3390/jof8020168. [PubMed:35205922 ]
Safwan S, Hsiao G, Lee TH, Lee CK: Bioactive compounds from an endophytic fungi Nigrospora aurantiaca. Bot Stud. 2021 Oct 26;62(1):18. doi: 10.1186/s40529-021-00324-7. [PubMed:34698886 ]
Li J, Shi L, Xu S, Gu S, Wen X, Xu D, Luo J, Huang Y, Wang M: Optimal fermentation time for Nigrospora-fermented tea rich in bostrycin. J Sci Food Agric. 2021 Apr;101(6):2483-2490. doi: 10.1002/jsfa.10874. Epub 2020 Nov 10. [PubMed:33058154 ]
Feng S, Wang W: Bioactivities and Structure-Activity Relationships of Natural Tetrahydroanthraquinone Compounds: A Review. Front Pharmacol. 2020 May 27;11:799. doi: 10.3389/fphar.2020.00799. eCollection 2020. [PubMed:32536871 ]
Jie J, Shi L, Yue S, Wang M, Zhang J: Bostrycin inhibits growth of tongue squamous cell carcinoma cells by inducing mitochondrial apoptosis. Transl Cancer Res. 2020 Jun;9(6):3926-3936. doi: 10.21037/tcr-19-2076. [PubMed:35117759 ]

Showing NP-Card for Bostrycin (NP0141128)

MOL for NP0141128 (Bostrycin)

3D MOL for NP0141128 (Bostrycin)

3D SDF for NP0141128 (Bostrycin)

3D-SDF for NP0141128 (Bostrycin)

PDB for NP0141128 (Bostrycin)

3D PDB for NP0141128 (Bostrycin)

SMILES for NP0141128 (Bostrycin)

INCHI for NP0141128 (Bostrycin)

Structure for NP0141128 (Bostrycin)

3D Structure for NP0141128 (Bostrycin)