NP-MRD: Showing NP-Card for Asperustin J (NP0332895)

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Record Information

Version

1.0

Created at

2024-05-01 21:54:25 UTC

Updated at

2024-05-03 00:10:50 UTC

NP-MRD ID

NP0332895

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asperustin J

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01142300312D          

 32 36  0  0  1  0            999 V2000
    2.3592   -0.4267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2513   -1.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9057   -1.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680   -1.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3224   -1.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847   -1.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -0.8005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7390   -2.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5503   -1.9707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1183   -1.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8629   -1.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7549   -2.5457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1568   -1.2456    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9437   -2.6958    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3372   -3.4210    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3757   -3.2941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6311   -2.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8688   -3.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145   -2.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522   -3.0673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7759   -0.6136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978   -2.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355   -2.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9276   -3.6983    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5820   -4.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1653   -4.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0574   -4.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9495   -5.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395   -4.7238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753   -4.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3811   -2.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4890   -1.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  1  0  0  0
  9 14  1  0  0  0  0
 14 12  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  8 17  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  5 19  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 21  2  0  0  0  0
  3 22  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  2  0  0  0  0
  2 32  1  0  0  0  0
M  END


  Mrv2104 01142300312D          

 32 36  0  0  1  0            999 V2000
    2.3592   -0.4267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2513   -1.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9057   -1.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680   -1.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3224   -1.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847   -1.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -0.8005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7390   -2.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5503   -1.9707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1183   -1.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8629   -1.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7549   -2.5457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1568   -1.2456    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9437   -2.6958    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3372   -3.4210    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3757   -3.2941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6311   -2.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8688   -3.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145   -2.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522   -3.0673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7759   -0.6136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978   -2.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355   -2.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9276   -3.6983    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5820   -4.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1653   -4.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0574   -4.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9495   -5.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395   -4.7238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753   -4.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3811   -2.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4890   -1.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  1  0  0  0
  9 14  1  0  0  0  0
 14 12  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  8 17  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  5 19  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 21  2  0  0  0  0
  3 22  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  2  0  0  0  0
  2 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332895

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O8/c1-22(2,27)8-12(24)9-3-4-11(23)16-19(26)17-14(29-20(9)16)7-13-15(18(17)25)10-5-6-28-21(10)30-13/h3-7,10,12,21,23-25,27H,8H2,1-2H3/t10-,12-,21+/m0/s1

> <INCHI_KEY>
GKGDJDFOEXXSFL-HPPJEKTDSA-N

> <FORMULA>
C22H20O8

> <MOLECULAR_WEIGHT>
412.394

> <EXACT_MASS>
412.115817604

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
41.50337073590279

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,8R)-15-[(1S)-1,3-dihydroxy-3-methylbutyl]-2,18-dihydroxy-7,9,13-trioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,5,10,14,16,18-heptaen-20-one

> <JCHEM_LOGP>
2.962124357666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.537828168935969

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.82543021423195

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6674100338062656

> <JCHEM_POLAR_SURFACE_AREA>
125.68

> <JCHEM_REFRACTIVITY>
105.9211

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,8R)-15-[(1S)-1,3-dihydroxy-3-methylbutyl]-2,18-dihydroxy-7,9,13-trioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,5,10,14,16,18-heptaen-20-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JAN-23         0                                  
HETATM    1  O   UNK     0       4.404  -0.796   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.202  -2.323   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.424  -3.261   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.847  -2.672   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.068  -3.610   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.491  -3.021   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.693  -1.494   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.713  -3.959   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.227  -3.679   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.288  -2.562   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.677  -3.225   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.476  -4.752   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0      11.493  -2.325   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0      12.962  -5.032   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0      13.696  -6.386   0.000  0.00  0.00           H+0
HETATM   16  O   UNK     0      11.901  -6.149   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.511  -5.486   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.088  -6.075   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.867  -5.137   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.444  -5.726   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       7.048  -1.145   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.223  -4.788   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.800  -5.377   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.598  -6.904   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.820  -7.841   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.175  -7.492   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.974  -9.019   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.772 -10.546   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.447  -8.818   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.501  -9.221   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.578  -4.439   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.780  -2.912   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   17                                                  
CONECT    9    8   10   13   14                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   14                                                       
CONECT   13    9                                                            
CONECT   14    9   12   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17    8   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19    5   18   20                                                  
CONECT   20   19   22                                                       
CONECT   21    4                                                            
CONECT   22    3   20   23                                                  
CONECT   23   22   24   31                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   23   32                                                       
CONECT   32   31    2                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₀O₈

Average Mass

412.3940 Da

Monoisotopic Mass

412.11582 Da

IUPAC Name

(4S,8R)-15-[(1S)-1,3-dihydroxy-3-methylbutyl]-2,18-dihydroxy-7,9,13-trioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,5,10,14,16,18-heptaen-20-one

Traditional Name

(4S,8R)-15-[(1S)-1,3-dihydroxy-3-methylbutyl]-2,18-dihydroxy-7,9,13-trioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,5,10,14,16,18-heptaen-20-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H20O8/c1-22(2,27)8-12(24)9-3-4-11(23)16-19(26)17-14(29-20(9)16)7-13-15(18(17)25)10-5-6-28-21(10)30-13/h3-7,10,12,21,23-25,27H,8H2,1-2H3/t10-,12-,21+/m0/s1

InChI Key

GKGDJDFOEXXSFL-HPPJEKTDSA-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
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
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
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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
ustus NRRL 5856		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
logP	2.96	ChemAxon
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.92 m³·mol⁻¹	ChemAxon
Polarizability	41.5 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

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 J (NP0332895)

MOL for NP0332895 (Asperustin J)

3D MOL for NP0332895 (Asperustin J)

3D SDF for NP0332895 (Asperustin J)

3D-SDF for NP0332895 (Asperustin J)

PDB for NP0332895 (Asperustin J)

3D PDB for NP0332895 (Asperustin J)

SMILES for NP0332895 (Asperustin J)

INCHI for NP0332895 (Asperustin J)

Structure for NP0332895 (Asperustin J)

3D Structure for NP0332895 (Asperustin J)