NP-MRD: Showing NP-Card for Asperustin D (NP0332889)

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Record Information

Version

1.0

Created at

2024-05-01 21:17:49 UTC

Updated at

2024-05-03 00:10:47 UTC

NP-MRD ID

NP0332889

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asperustin D

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01132323542D          

 30 34  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
   -0.1269    1.0994    0.0000 C   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
 21 24  1  0  0  0  0
 19 25  1  1  0  0  0
 19 26  1  0  0  0  0
 26 24  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 18 29  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 13 30  1  0  0  0  0
M  END


  Mrv2104 01132323542D          

 30 34  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
   -0.1269    1.0994    0.0000 C   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
 21 24  1  0  0  0  0
 19 25  1  1  0  0  0
 19 26  1  0  0  0  0
 26 24  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 18 29  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 13 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332889

> <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

> <INCHI_IDENTIFIER>
InChI=1S/C20H17ClO7/c1-23-13-6-8-14-11(27-20(8)28-13)7-12-16(19(14)25-3)17(22)15-10(26-12)5-4-9(21)18(15)24-2/h4-5,7-8,13,20H,6H2,1-3H3/t8-,13-,20-/m0/s1

> <INCHI_KEY>
SDXQRVRHGLRZGN-LAGHKUAJSA-N

> <FORMULA>
C20H17ClO7

> <MOLECULAR_WEIGHT>
404.8

> <EXACT_MASS>
404.0662806

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
39.933194623778455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,6S,8S)-17-chloro-2,6,18-trimethoxy-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-20-one

> <JCHEM_LOGP>
3.2367524743333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.548739723462798

> <JCHEM_POLAR_SURFACE_AREA>
72.45000000000002

> <JCHEM_REFRACTIVITY>
98.78810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,6S,8S)-17-chloro-2,6,18-trimethoxy-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-20-one

> <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      -0.237   2.052   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.359   5.853   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0       4.342   3.426   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       2.873   6.133   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       2.139   7.487   0.000  0.00  0.00           H+0
HETATM   28  O   UNK     0       3.934   7.250   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.323   6.586   0.000  0.00  0.00           C+0
HETATM   30  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   30                                                  
CONECT   14   13    2   15                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   29                                                  
CONECT   19   18   20   25   26                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   26                                                       
CONECT   25   19                                                            
CONECT   26   19   24   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   18   28   30                                                  
CONECT   30   29   13                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₇ClO₇

Average Mass

404.8000 Da

Monoisotopic Mass

404.06628 Da

IUPAC Name

(4S,6S,8S)-17-chloro-2,6,18-trimethoxy-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-20-one

Traditional Name

(4S,6S,8S)-17-chloro-2,6,18-trimethoxy-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-20-one

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

InChI Identifier

InChI=1S/C20H17ClO7/c1-23-13-6-8-14-11(27-20(8)28-13)7-12-16(19(14)25-3)17(22)15-10(26-12)5-4-9(21)18(15)24-2/h4-5,7-8,13,20H,6H2,1-3H3/t8-,13-,20-/m0/s1

InChI Key

SDXQRVRHGLRZGN-LAGHKUAJSA-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
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_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
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	3.24	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	72.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	98.79 m³·mol⁻¹	ChemAxon
Polarizability	39.93 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 D (NP0332889)

MOL for NP0332889 (Asperustin D)

3D MOL for NP0332889 (Asperustin D)

3D SDF for NP0332889 (Asperustin D)

3D-SDF for NP0332889 (Asperustin D)

PDB for NP0332889 (Asperustin D)

3D PDB for NP0332889 (Asperustin D)

SMILES for NP0332889 (Asperustin D)

INCHI for NP0332889 (Asperustin D)

Structure for NP0332889 (Asperustin D)

3D Structure for NP0332889 (Asperustin D)