NP-MRD: Showing NP-Card for alaguignardic acid (NP0042099)

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Record Information

Version

2.0

Created at

2021-06-20 23:50:40 UTC

Updated at

2021-06-30 00:16:59 UTC

NP-MRD ID

NP0042099

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alaguignardic acid

Provided By

JEOL Database JEOL Logo

Description

Alaguignardic acid is also known as alaguignardate. alaguignardic acid is found in Guignardia bidwellii. alaguignardic acid was first documented in 2017 (PMID: 28827628). Based on a literature review very few articles have been published on Alaguignardic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101503D          

 27 28  0  0  0  0            999 V2000
    1.0423   -0.2701   -2.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820    0.9243   -1.7070 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5872    1.9958   -1.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0832    2.3827   -0.4928 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9985    2.5367   -2.7107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6116    1.4690   -2.4424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6594    1.5773   -1.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398    2.0732   -1.8439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098    0.9548   -0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0056    0.8795    0.7338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6437    0.2749    2.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6013   -0.4896    2.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3086   -1.0546    3.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596   -0.8505    4.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053   -0.0778    3.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3975    0.4873    2.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0692    0.4631   -0.4175 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3437    0.0074   -3.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2853   -1.0577   -2.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9054   -0.7035   -1.9563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6590    3.2133   -2.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0183    1.2763    0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5835   -0.6591    2.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570   -1.6519    4.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8317   -1.2885    5.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8670    0.0912    4.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3589    1.1003    2.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0  0  0  0
 12 13  2  0  0  0  0
 10 11  1  0  0  0  0
 13 14  1  0  0  0  0
  7  6  1  0  0  0  0
  6  2  1  0  0  0  0
  2 17  1  0  0  0  0
 17  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2  3  1  1  0  0  0
 14 15  2  0  0  0  0
  3  5  1  0  0  0  0
 11 12  1  0  0  0  0
  3  4  2  0  0  0  0
 15 16  1  0  0  0  0
  2  1  1  0  0  0  0
 16 11  2  0  0  0  0
  7  8  2  0  0  0  0
 10 22  1  0  0  0  0
 12 23  1  0  0  0  0
 13 24  1  0  0  0  0
 14 25  1  0  0  0  0
 15 26  1  0  0  0  0
 16 27  1  0  0  0  0
  5 21  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
M  END


  Mrv1652306212101503D          

 27 28  0  0  0  0            999 V2000
    1.0423   -0.2701   -2.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820    0.9243   -1.7070 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5872    1.9958   -1.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0832    2.3827   -0.4928 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9985    2.5367   -2.7107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6116    1.4690   -2.4424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6594    1.5773   -1.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398    2.0732   -1.8439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098    0.9548   -0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0056    0.8795    0.7338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6437    0.2749    2.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6013   -0.4896    2.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3086   -1.0546    3.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596   -0.8505    4.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053   -0.0778    3.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3975    0.4873    2.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0692    0.4631   -0.4175 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3437    0.0074   -3.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2853   -1.0577   -2.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9054   -0.7035   -1.9563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6590    3.2133   -2.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0183    1.2763    0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5835   -0.6591    2.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570   -1.6519    4.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8317   -1.2885    5.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8670    0.0912    4.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3589    1.1003    2.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0  0  0  0
 12 13  2  0  0  0  0
 10 11  1  0  0  0  0
 13 14  1  0  0  0  0
  7  6  1  0  0  0  0
  6  2  1  0  0  0  0
  2 17  1  0  0  0  0
 17  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2  3  1  1  0  0  0
 14 15  2  0  0  0  0
  3  5  1  0  0  0  0
 11 12  1  0  0  0  0
  3  4  2  0  0  0  0
 15 16  1  0  0  0  0
  2  1  1  0  0  0  0
 16 11  2  0  0  0  0
  7  8  2  0  0  0  0
 10 22  1  0  0  0  0
 12 23  1  0  0  0  0
 13 24  1  0  0  0  0
 14 25  1  0  0  0  0
 15 26  1  0  0  0  0
 16 27  1  0  0  0  0
  5 21  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042099

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]1(OC(=O)\C(O1)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O5/c1-12(11(14)15)16-9(10(13)17-12)7-8-5-3-2-4-6-8/h2-7H,1H3,(H,14,15)/b9-7-/t12-/m0/s1

> <INCHI_KEY>
CXQNWERAIOVCAY-UPZNUWHASA-N

> <FORMULA>
C12H10O5

> <MOLECULAR_WEIGHT>
234.207

> <EXACT_MASS>
234.052823422

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
22.55296536971825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,5Z)-2-methyl-4-oxo-5-(phenylmethylidene)-1,3-dioxolane-2-carboxylic acid

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
2.294260953666666

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0465420332349087

> <JCHEM_PKA_STRONGEST_BASIC>
-5.2130468723503

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
58.57280000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5Z)-2-methyl-4-oxo-5-(phenylmethylidene)-1,3-dioxolane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       1.042  -0.270  -2.473  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.482   0.924  -1.707  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.587   1.996  -1.541  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.083   2.383  -0.493  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.999   2.537  -2.711  0.00  0.00           O+0
HETATM    6  O   UNK     0      -0.612   1.469  -2.442  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.659   1.577  -1.595  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.740   2.073  -1.844  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.210   0.955  -0.343  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.006   0.880   0.734  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.644   0.275   2.023  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.601  -0.490   2.702  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.309  -1.055   3.946  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.060  -0.851   4.529  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.105  -0.078   3.870  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.398   0.487   2.627  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.069   0.463  -0.418  0.00  0.00           O+0
HETATM   18  H   UNK     0       1.344   0.007  -3.489  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.285  -1.058  -2.563  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.905  -0.704  -1.956  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.659   3.213  -2.450  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.018   1.276   0.676  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.583  -0.659   2.267  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.057  -1.652   4.461  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.832  -1.289   5.497  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.867   0.091   4.326  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.359   1.100   2.141  0.00  0.00           H+0
CONECT    1    2   18   19   20                                             
CONECT    2    6   17    3    1                                             
CONECT    3    2    5    4                                                  
CONECT    4    3                                                            
CONECT    5    3   21                                                       
CONECT    6    7    2                                                       
CONECT    7    9    6    8                                                  
CONECT    8    7                                                            
CONECT    9    7   17   10                                                  
CONECT   10   11    9   22                                                  
CONECT   11   10   12   16                                                  
CONECT   12   13   11   23                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16   26                                                  
CONECT   16   15   11   27                                                  
CONECT   17    2    9                                                       
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    5                                                            
CONECT   22   10                                                            
CONECT   23   12                                                            
CONECT   24   13                                                            
CONECT   25   14                                                            
CONECT   26   15                                                            
CONECT   27   16                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
Alaguignardate	Generator

Chemical Formula

C₁₂H₁₀O₅

Average Mass

234.2070 Da

Monoisotopic Mass

234.05282 Da

IUPAC Name

(2S,5Z)-2-methyl-4-oxo-5-(phenylmethylidene)-1,3-dioxolane-2-carboxylic acid

Traditional Name

(2S,5Z)-2-methyl-4-oxo-5-(phenylmethylidene)-1,3-dioxolane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@@]1(OC(=O)\C(O1)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C12H10O5/c1-12(11(14)15)16-9(10(13)17-12)7-8-5-3-2-4-6-8/h2-7H,1H3,(H,14,15)/b9-7-/t12-/m0/s1

InChI Key

CXQNWERAIOVCAY-UPZNUWHASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phyllosticta ampelicida	JEOL database	Buckel L., et al, Phytochemistry 89, 96 (2013)

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	1.82	ALOGPS
logP	2.29	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.05	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.57 m³·mol⁻¹	ChemAxon
Polarizability	22.55 Å³	ChemAxon
Number of Rings	2	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

102435402

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Buckel I, Andernach L, Schuffler A, Piepenbring M, Opatz T, Thines E: Phytotoxic dioxolanones are potential virulence factors in the infection process of Guignardia bidwellii. Sci Rep. 2017 Aug 21;7(1):8926. doi: 10.1038/s41598-017-09157-6. [PubMed:28827628 ]
Buckel L., et al. (2013). Buckel L., et al, Phytochemistry 89, 96 (2013) . Phytochem..

Showing NP-Card for alaguignardic acid (NP0042099)

MOL for NP0042099 (alaguignardic acid)

3D MOL for NP0042099 (alaguignardic acid)

3D SDF for NP0042099 (alaguignardic acid)

3D-SDF for NP0042099 (alaguignardic acid)

PDB for NP0042099 (alaguignardic acid)

3D PDB for NP0042099 (alaguignardic acid)

SMILES for NP0042099 (alaguignardic acid)

INCHI for NP0042099 (alaguignardic acid)

Structure for NP0042099 (alaguignardic acid)

3D Structure for NP0042099 (alaguignardic acid)