NP-MRD: Showing NP-Card for grifulvin v (NP0322785)

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Record Information

Version

2.0

Created at

2022-09-12 01:46:07 UTC

Updated at

2022-09-12 01:46:07 UTC

NP-MRD ID

NP0322785

Secondary Accession Numbers

None

Natural Product Identification

Common Name

grifulvin v

Description

Polygris, also known as grisefuline or grispeg, belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Polygris is an extremely weak basic (essentially neutral) compound (based on its pKa). grifulvin v is found in Axinella verrucosa, Penicillium aethiopicum, Penicillium griseofulvum, Penicillium raistrickii and Penicillium solitum. Polygris is a potentially toxic compound.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.7064    3.4918   -0.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2564    2.3244   -1.3597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6101    1.0437   -0.9070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9055    0.8161   -0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3382   -0.4929   -0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5322   -0.8515   -0.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2846   -1.3316    0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1330   -1.3591   -0.6127 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1625   -2.3869   -0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5492    0.0230   -0.6962 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6126    0.0163   -1.7592 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6499   -0.0588   -1.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9077   -0.3087   -1.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0133   -0.5855   -3.4639 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0552   -0.3429   -1.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2996   -0.5922   -1.5763 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4535   -0.6193   -0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9572   -0.1222    0.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7505    0.1280    0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6414    0.3516    2.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7056    0.3506    3.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6221    0.1520    0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7827    0.3865    0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2260    0.8012    1.5958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3609    3.5178    0.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4265    4.4094   -1.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8290    3.4906   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6069    1.6189   -0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729   -0.8299    1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6379   -2.3599    0.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5632   -1.6300   -1.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9224   -2.2402    0.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2421   -2.4306   -0.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6442   -3.3840   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3620   -1.3896    0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6889    0.3683   -0.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3068   -0.9873   -1.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8515   -0.1394    0.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3605    0.8645    4.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5321    0.9487    2.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0476   -0.6608    3.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 19  1  0
 19 18  2  0
 18 15  1  0
 15 16  1  0
 16 17  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 22  2  0
 22 23  1  0
 23 24  2  0
 23 10  1  0
 10 11  1  6
 10  8  1  0
  8  9  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
 22 19  1  0
  3 10  1  0
 11 12  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 18 38  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
  8 31  1  6
  9 32  1  0
  9 33  1  0
  9 34  1  0
  7 29  1  0
  7 30  1  0
  4 28  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  END


  Mrv0541 02241205502D          

 24 26  0  0  0  0            999 V2000
    0.0000   -1.6500    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
    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
    0.7145    2.0625    0.0000 Cl  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
    2.2136    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -1.0799    0.0000 O   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
  1  2  1  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
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  3 24  1  0  0  0  0
 10 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0322785

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C(Cl)C2=C1C(=O)C1(O2)C(C)CC(=O)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3

> <INCHI_KEY>
DDUHZTYCFQRHIY-UHFFFAOYSA-N

> <FORMULA>
C17H17ClO6

> <MOLECULAR_WEIGHT>
352.766

> <EXACT_MASS>
352.071365983

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
34.15424470856199

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.172137458333333

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.68867051547463

> <JCHEM_PKA_STRONGEST_BASIC>
-4.322861287850263

> <JCHEM_POLAR_SURFACE_AREA>
71.06

> <JCHEM_REFRACTIVITY>
87.84589999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
grifulvin V

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0       1.334   3.850   0.000  0.00  0.00          Cl+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.132   2.016   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.807   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.037   3.437   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.347   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.117   0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.657   0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.347  -0.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.807  -0.564   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.037  -1.897   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.807  -3.231   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.132  -0.476   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.132  -2.016   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   24                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19   22                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   12   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    3   10                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
Grisefuline	MeSH
GrisPEG	MeSH
Fulvicin u F	MeSH
Grisactin	MeSH
Fulvicin-u-F	MeSH
Gris-peg	MeSH
Grifulvin V	MeSH
Gris peg	MeSH
FulvicinUF	MeSH
Griseofulvin	MeSH
V, Grifulvin	MeSH

Chemical Formula

C₁₇H₁₇ClO₆

Average Mass

352.7660 Da

Monoisotopic Mass

352.07137 Da

IUPAC Name

7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

Traditional Name

grifulvin V

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C(Cl)C2=C1C(=O)C1(O2)C(C)CC(=O)C=C1OC

InChI Identifier

InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3

InChI Key

DDUHZTYCFQRHIY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Axinella verrucosa	LOTUS Database	35616633
Penicillium aethiopicum	LOTUS Database	35616633
Penicillium griseofulvum	LOTUS Database	35616633
Penicillium raistrickii	LOTUS Database	35616633
Penicillium solitum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Coumaran
Benzofuran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Cyclohexenone
Aryl chloride
Aryl halide
Benzenoid
Vinylogous ester
Ketone
Cyclic ketone
Ether
Oxacycle
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	2.71	ALOGPS
logP	2.17	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	17.69	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	87.85 m³·mol⁻¹	ChemAxon
Polarizability	34.15 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

3512

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for grifulvin v (NP0322785)

MOL for NP0322785 (grifulvin v)

3D MOL for NP0322785 (grifulvin v)

3D SDF for NP0322785 (grifulvin v)

3D-SDF for NP0322785 (grifulvin v)

PDB for NP0322785 (grifulvin v)

3D PDB for NP0322785 (grifulvin v)

SMILES for NP0322785 (grifulvin v)

INCHI for NP0322785 (grifulvin v)

Structure for NP0322785 (grifulvin v)

3D Structure for NP0322785 (grifulvin v)