NP-MRD: Showing NP-Card for Versicomide H (NP0331759)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2023-08-10 08:00:35 UTC

Updated at

2024-09-03 04:16:46 UTC

NP-MRD ID

NP0331759

Natural Product DOI

https://doi.org/10.57994/0796

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Versicomide H

Description

Versicomide H belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Versicomide H was first documented in 2024 (PMID: 37455565). Based on a literature review very few articles have been published on Versicomide H.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 08102308002D          

 25 27  0  0  1  0            999 V2000
    2.1434   -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
    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  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  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
    5.7158    0.0000    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
    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
    2.1434    1.2375    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 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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 N   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   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
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 18 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331759

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C(C)=C1/NC(=O)[C@@H](C(C)C)N2C(=O)C3=CC(OC)=CC=C3N=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H23N3O3/c1-6-11(4)15-17-20-14-8-7-12(25-5)9-13(14)19(24)22(17)16(10(2)3)18(23)21-15/h7-10,16H,6H2,1-5H3,(H,21,23)/b15-11-/t16-/m1/s1

> <INCHI_KEY>
DSVLRXYQNBWUSM-UVQBRAAOSA-N

> <FORMULA>
C19H23N3O3

> <MOLECULAR_WEIGHT>
341.411

> <EXACT_MASS>
341.173941613

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.36828800340254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.490899736666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.192356138357786

> <JCHEM_PKA_STRONGEST_BASIC>
4.688474229860912

> <JCHEM_POLAR_SURFACE_AREA>
71.0

> <JCHEM_REFRACTIVITY>
97.95309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1Z,4R)-1-(butan-2-ylidene)-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  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.669   0.000   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  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12    2   14                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   12   21                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21                                                            
CONECT   25   18                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₃N₃O₃

Average Mass

341.4110 Da

Monoisotopic Mass

341.17394 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC\C(C)=C1/NC(=O)[C@@H](C(C)C)N2C(=O)C3=CC(OC)=CC=C3N=C12

InChI Identifier

InChI=1S/C19H23N3O3/c1-6-11(4)15-17-20-14-8-7-12(25-5)9-13(14)19(24)22(17)16(10(2)3)18(23)21-15/h7-10,16H,6H2,1-5H3,(H,21,23)/b15-11-/t16-/m1/s1

InChI Key

DSVLRXYQNBWUSM-UVQBRAAOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	llx7772699@163.com	Not Available	Not Available	2024-05-08	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	llx7772699@163.com	Not Available	Not Available	2024-05-08	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	llx7772699@163.com	Not Available	Not Available	2024-05-08	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	llx7772699@163.com	Not Available	Not Available	2024-05-08	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	llx7772699@163.com	Not Available	Not Available	2024-05-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, 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, CDCl₃, 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

Description

This compound belongs to the class of organic compounds known as valine and derivatives. These are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Valine and derivatives

Alternative Parents

Substituents

Valine or derivatives
Diazanaphthalene
Quinazoline
Anisole
Pyrimidone
Alkyl aryl ether
Fatty acyl
Benzenoid
Pyrimidine
Piperazine
N-acyl-amine
1,4,5,6-tetrahydropyrimidine
Hydropyrimidine
Fatty amide
1,4-diazinane
Heteroaromatic compound
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	2.49	ChemAxon
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	4.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.95 m³·mol⁻¹	ChemAxon
Polarizability	37.37 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

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

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 H (NP0331759)

MOL for NP0331759 (Versicomide H)

3D MOL for NP0331759 (Versicomide H)

3D SDF for NP0331759 (Versicomide H)

3D-SDF for NP0331759 (Versicomide H)

PDB for NP0331759 (Versicomide H)

3D PDB for NP0331759 (Versicomide H)

SMILES for NP0331759 (Versicomide H)

INCHI for NP0331759 (Versicomide H)

Structure for NP0331759 (Versicomide H)

3D Structure for NP0331759 (Versicomide H)