NP-MRD: Showing NP-Card for Asperustin B (NP0332887)

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Record Information

Version

2.0

Created at

2024-05-01 21:07:07 UTC

Updated at

2024-09-03 04:20:35 UTC

NP-MRD ID

NP0332887

Natural Product DOI

https://doi.org/10.57994/2167

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asperustin B

Description

Asperustin B belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Asperustin B was first documented in 2024 (PMID: 38441877). Based on a literature review very few articles have been published on Asperustin B.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01132323432D          

 32 36  0  0  1  0            999 V2000
    4.7070    1.2033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8149    2.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5772    2.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2316    1.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237    1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7780    0.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9939    2.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6482    1.6474    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.1018    2.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4474    3.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6851    3.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307    3.6571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685    3.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1605    2.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3983    2.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2903    1.3902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5281    1.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7439    2.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9326    2.5604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3646    1.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6201    2.3175    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1051    1.9241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8084    2.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5335    1.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7866    3.1801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7280    3.1355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261    1.8353    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392    3.2856    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1457    4.0107    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1073    3.8838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8518    3.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6141    3.8440    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  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 19 27  1  1  0  0  0
 19 28  1  0  0  0  0
 28 26  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 18 31  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 13 32  1  0  0  0  0
M  END


  Mrv2104 01132323432D          

 32 36  0  0  1  0            999 V2000
    4.7070    1.2033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8149    2.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5772    2.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2316    1.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237    1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7780    0.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9939    2.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6482    1.6474    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.1018    2.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4474    3.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6851    3.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307    3.6571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685    3.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1605    2.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3983    2.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2903    1.3902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5281    1.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7439    2.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9326    2.5604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3646    1.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6201    2.3175    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1051    1.9241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8084    2.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5335    1.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7866    3.1801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7280    3.1355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261    1.8353    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392    3.2856    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1457    4.0107    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1073    3.8838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8518    3.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6141    3.8440    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  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 19 27  1  1  0  0  0
 19 28  1  0  0  0  0
 28 26  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 18 31  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 13 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332887

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12O[C@@H](C[C@@]1([H])C1=C(OC)C3=C(OC4=CC=C(Cl)C(OC)=C4C3=O)C=C1O2)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H17ClO8/c1-8(23)27-14-6-9-15-12(29-21(9)30-14)7-13-17(20(15)26-3)18(24)16-11(28-13)5-4-10(22)19(16)25-2/h4-5,7,9,14,21H,6H2,1-3H3/t9-,14-,21-/m0/s1

> <INCHI_KEY>
DYKVRXLGCJCZCP-RMIDZRHBSA-N

> <FORMULA>
C21H17ClO8

> <MOLECULAR_WEIGHT>
432.81

> <EXACT_MASS>
432.0611952

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
41.94226403282171

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,6R,8S)-17-chloro-2,18-dimethoxy-20-oxo-7,9,13-trioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,10,14,16,18-hexaen-6-yl acetate

> <JCHEM_LOGP>
3.0347513810000004

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.637689185125184

> <JCHEM_POLAR_SURFACE_AREA>
89.52000000000001

> <JCHEM_REFRACTIVITY>
103.1884

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,6R,8S)-17-chloro-2,18-dimethoxy-20-oxo-7,9,13-trioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,10,14,16,18-hexaen-6-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JAN-23         0                                  
HETATM    1  O   UNK     0       8.786   2.246   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.988   3.773   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.411   4.362   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.632   3.424   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.431   1.897   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.652   0.959   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.055   4.013   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0      14.277   3.075   0.000  0.00  0.00          Cl+0
HETATM    9  C   UNK     0      13.257   5.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.035   6.478   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.612   5.889   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.391   6.827   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.968   6.238   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.766   4.711   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.343   4.122   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.142   2.595   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.719   2.006   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.122   5.060   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.608   4.779   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.547   3.663   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.157   4.326   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.196   3.592   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.509   4.397   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.863   3.662   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.468   5.936   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.359   5.853   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       4.342   3.426   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0       2.873   6.133   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0       2.139   7.487   0.000  0.00  0.00           H+0
HETATM   30  O   UNK     0       3.934   7.250   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.323   6.586   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.746   7.175   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    3   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   32                                                  
CONECT   14   13    2   15                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   31                                                  
CONECT   19   18   20   27   28                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   28                                                       
CONECT   27   19                                                            
CONECT   28   19   26   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   18   30   32                                                  
CONECT   32   31   13                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₁₇ClO₈

Average Mass

432.8100 Da

Monoisotopic Mass

432.06120 Da

IUPAC Name

(4S,6R,8S)-17-chloro-2,18-dimethoxy-20-oxo-7,9,13-trioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,10,14,16,18-hexaen-6-yl acetate

Traditional Name

(4S,6R,8S)-17-chloro-2,18-dimethoxy-20-oxo-7,9,13-trioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,10,14,16,18-hexaen-6-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@]12O[C@@H](C[C@@]1([H])C1=C(OC)C3=C(OC4=CC=C(Cl)C(OC)=C4C3=O)C=C1O2)OC(C)=O

InChI Identifier

InChI=1S/C21H17ClO8/c1-8(23)27-14-6-9-15-12(29-21(9)30-14)7-13-17(20(15)26-3)18(24)16-11(28-13)5-4-10(22)19(16)25-2/h4-5,7,9,14,21H,6H2,1-3H3/t9-,14-,21-/m0/s1

InChI Key

DYKVRXLGCJCZCP-RMIDZRHBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	ruanhl@hust.edu.cn	Huazhong University of Science and Technology	Han-Li Ruan	2024-05-01	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	ruanhl@hust.edu.cn	Huazhong University of Science and Technology	Han-Li Ruan	2024-05-01	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	ruanhl@hust.edu.cn	Huazhong University of Science and Technology	Han-Li Ruan	2024-05-01	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	ruanhl@hust.edu.cn	Huazhong University of Science and Technology	Han-Li Ruan	2024-05-01	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	ruanhl@hust.edu.cn	Huazhong University of Science and Technology	Han-Li Ruan	2024-05-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	ruanhl@hust.edu.cn	Huazhong University of Science and Technology	Han-Li Ruan	2024-05-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	ruanhl@hust.edu.cn	Huazhong University of Science and Technology	Han-Li Ruan	2024-05-01	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
ustus NRRL 5856		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Furanochromone
Chromone
Coumaran
Furofuran
Anisole
Pyranone
Dihydropyranone
Alkyl aryl ether
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Alpha,beta-unsaturated ketone
Tetrahydrofuran
Enone
Acryloyl-group
Ketone
Carboxylic acid ester
Oxacycle
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen 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	3.03	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	89.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.19 m³·mol⁻¹	ChemAxon
Polarizability	41.94 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chang JL, Gan YT, Zhou YH, Peng XG, Xie ZY, Meng X, Li SM, Ruan HL: Asperustins A-J: Austocystins with Immunosuppressive and Cytotoxic Activities from Aspergillus ustus NRRL 5856. J Nat Prod. 2024 Apr 26;87(4):966-975. doi: 10.1021/acs.jnatprod.3c01243. Epub 2024 Mar 5. [PubMed:38441877 ]

Showing NP-Card for Asperustin B (NP0332887)

MOL for NP0332887 (Asperustin B)

3D MOL for NP0332887 (Asperustin B)

3D SDF for NP0332887 (Asperustin B)

3D-SDF for NP0332887 (Asperustin B)

PDB for NP0332887 (Asperustin B)

3D PDB for NP0332887 (Asperustin B)

SMILES for NP0332887 (Asperustin B)

INCHI for NP0332887 (Asperustin B)

Structure for NP0332887 (Asperustin B)

3D Structure for NP0332887 (Asperustin B)