NP-MRD: Showing NP-Card for Versicomide G (NP0331762)

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Record Information

Version

1.0

Created at

2023-08-10 08:01:06 UTC

Updated at

2024-05-08 22:21:23 UTC

NP-MRD ID

NP0331762

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Versicomide G

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 08102308012D          

 26 28  0  0  1  0            999 V2000
    2.1434    2.0625    0.0000 O   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
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1027   -1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0421   -1.0445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3242   -1.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7939   -2.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296   -0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   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
    2.1434   -0.4125    0.0000 N   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
    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
    0.0000   -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 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
    0.7145    1.2375    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
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  6  0  0  0
  8 16  2  0  0  0  0
  3 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  2  0  0  0  0
  2 19  1  0  0  0  0
 19 20  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 19 26  1  0  0  0  0
M  END


  Mrv2104 08102308012D          

 26 28  0  0  1  0            999 V2000
    2.1434    2.0625    0.0000 O   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
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1027   -1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0421   -1.0445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3242   -1.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7939   -2.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296   -0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   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
    2.1434   -0.4125    0.0000 N   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
    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
    0.0000   -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 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
    0.7145    1.2375    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
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  6  0  0  0
  8 16  2  0  0  0  0
  3 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  2  0  0  0  0
  2 19  1  0  0  0  0
 19 20  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 19 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331762

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@]1(O)NC(=O)[C@@H](C(C)C)N2C(=O)C3=C(C=CC(OC)=C3)N=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H25N3O4/c1-6-11(4)19(25)18-20-14-8-7-12(26-5)9-13(14)17(24)22(18)15(10(2)3)16(23)21-19/h7-11,15,25H,6H2,1-5H3,(H,21,23)/t11-,15+,19+/m0/s1

> <INCHI_KEY>
IYHAGJZYRGYJDU-SVBQJQNYSA-N

> <FORMULA>
C19H25N3O4

> <MOLECULAR_WEIGHT>
359.426

> <EXACT_MASS>
359.184506297

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.458821647365404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4R)-1-[(2S)-butan-2-yl]-1-hydroxy-8-methoxy-4-(propan-2-yl)-1H,2H,3H,4H,6H-pyrazino[2,1-b]quinazoline-3,6-dione

> <JCHEM_LOGP>
2.6407331196666677

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.23243602392447

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.979784342106912

> <JCHEM_PKA_STRONGEST_BASIC>
4.516590096238937

> <JCHEM_POLAR_SURFACE_AREA>
91.23000000000002

> <JCHEM_REFRACTIVITY>
98.1718

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R)-1-[(2S)-butan-2-yl]-1-hydroxy-4-isopropyl-8-methoxy-2H,4H-pyrazino[2,1-b]quinazoline-3,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-AUG-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-AUG-23         0                                  
HETATM    1  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       8.002  -0.000   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.658  -1.950   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.679  -1.950   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.205  -3.397   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.215  -4.577   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.162  -1.682   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   17                                             
CONECT   11   10                                                            
CONECT   12   10   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16    8                                                            
CONECT   17    3   10   18                                                  
CONECT   18   17   20                                                       
CONECT   19    2   20   26                                                  
CONECT   20   19   18   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   19                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₅N₃O₄

Average Mass

359.4260 Da

Monoisotopic Mass

359.18451 Da

IUPAC Name

(1R,4R)-1-[(2S)-butan-2-yl]-1-hydroxy-8-methoxy-4-(propan-2-yl)-1H,2H,3H,4H,6H-pyrazino[2,1-b]quinazoline-3,6-dione

Traditional Name

(1R,4R)-1-[(2S)-butan-2-yl]-1-hydroxy-4-isopropyl-8-methoxy-2H,4H-pyrazino[2,1-b]quinazoline-3,6-dione

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@]1(O)NC(=O)[C@@H](C(C)C)N2C(=O)C3=C(C=CC(OC)=C3)N=C12

InChI Identifier

InChI=1S/C19H25N3O4/c1-6-11(4)19(25)18-20-14-8-7-12(26-5)9-13(14)17(24)22(18)15(10(2)3)16(23)21-19/h7-11,15,25H,6H2,1-5H3,(H,21,23)/t11-,15+,19+/m0/s1

InChI Key

IYHAGJZYRGYJDU-SVBQJQNYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	llx7772699@163.com	Not Available	Not Available	2024-05-08	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	llx7772699@163.com	Not Available	Not Available	2024-05-08	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental)	llx7772699@163.com	Not Available	Not Available	2024-05-08	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	llx7772699@163.com	Not Available	Not Available	2024-05-08	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	llx7772699@163.com	Not Available	Not Available	2024-05-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C2D6OS, experimental)	llx7772699@163.com	Not Available	Not Available	2024-05-08	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500, C2D6OS, simulated)	Not Available	Not Available	Not Available	2024-05-08	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
versicolor HYQZ-215		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	2.64	ChemAxon
pKa (Strongest Acidic)	9.98	ChemAxon
pKa (Strongest Basic)	4.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	98.17 m³·mol⁻¹	ChemAxon
Polarizability	38.46 Å³	ChemAxon
Number of Rings	3	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

Liao LX, Huang JG, Liu QP, Yao M, Wang WJ, Yang XL: Two new quinazoline alkaloids produced by Aspergillus versicolor and their antimicrobial activities. J Asian Nat Prod Res. 2024 Mar;26(3):320-327. doi: 10.1080/10286020.2023.2230895. Epub 2023 Jul 17. [PubMed:37455565 ]

Showing NP-Card for Versicomide G (NP0331762)

MOL for NP0331762 (Versicomide G)

3D MOL for NP0331762 (Versicomide G)

3D SDF for NP0331762 (Versicomide G)

3D-SDF for NP0331762 (Versicomide G)

PDB for NP0331762 (Versicomide G)

3D PDB for NP0331762 (Versicomide G)

SMILES for NP0331762 (Versicomide G)

INCHI for NP0331762 (Versicomide G)

Structure for NP0331762 (Versicomide G)

3D Structure for NP0331762 (Versicomide G)