NP-MRD: Showing NP-Card for Phenguignardic acid (NP0010959)

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Record Information

Version

2.0

Created at

2021-01-05 20:45:00 UTC

Updated at

2021-07-15 17:07:34 UTC

NP-MRD ID

NP0010959

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phenguignardic acid

Provided By

NPAtlas

Description

Phenguignardic acid is also known as phenguignardate. Phenguignardic acid is found in Guignardia and Phyllosticta ampelicida. Phenguignardic acid was first documented in 2012 (PMID: 22779915). Based on a literature review very few articles have been published on Phenguignardic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107423D          

 37 39  0  0  0  0            999 V2000
   -1.2171    1.5166    0.9674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6819    0.3971    0.7544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018    0.1154    0.8200 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856   -0.9600   -0.0807 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1664   -1.7146    0.1802 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3602   -0.8701    0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8595   -0.1931    1.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9808    0.6134    1.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6297    0.7465   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375    0.0678   -1.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152   -0.7307   -1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7722   -0.4610   -1.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472    0.7400   -1.7461 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9202   -1.3575   -2.5041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -1.7768    0.2775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029   -0.8683    0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591   -1.1567    0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393   -0.2189    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5741   -0.0199   -0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6164    0.8405   -0.5225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7580    1.5417    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8632    1.3782    1.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8057    0.4895    1.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0851   -2.1689    1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -2.5345   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3578   -0.2909    2.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3793    1.1503    1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5181    1.3835   -0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6679    0.1926   -2.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847   -1.2319   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.1594   -3.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8317   -2.1823   -0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4414   -0.5855   -1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3415    0.9890   -1.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6032    2.2238    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0033    1.9432    2.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1340    0.3677    2.3337 H   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 12  1  6  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 16  2  1  0  0  0  0
 23 18  1  0  0  0  0
 11  6  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  7 26  1  0  0  0  0
  8 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  0  0  0  0
 14 31  1  0  0  0  0
 17 32  1  0  0  0  0
 19 33  1  0  0  0  0
 20 34  1  0  0  0  0
 21 35  1  0  0  0  0
 22 36  1  0  0  0  0
 23 37  1  0  0  0  0
M  END

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -1.2171    1.5166    0.9674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6819    0.3971    0.7544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018    0.1154    0.8200 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856   -0.9600   -0.0807 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1664   -1.7146    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3602   -0.8701    0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8595   -0.1931    1.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9808    0.6134    1.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6297    0.7465   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375    0.0678   -1.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152   -0.7307   -1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7722   -0.4610   -1.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472    0.7400   -1.7461 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9202   -1.3575   -2.5041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -1.7768    0.2775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029   -0.8683    0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591   -1.1567    0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393   -0.2189    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5741   -0.0199   -0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6164    0.8405   -0.5225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7580    1.5417    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8632    1.3782    1.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8057    0.4895    1.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0851   -2.1689    1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -2.5345   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3578   -0.2909    2.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3793    1.1503    1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5181    1.3835   -0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6679    0.1926   -2.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847   -1.2319   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.1594   -3.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8317   -2.1823   -0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4414   -0.5855   -1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3415    0.9890   -1.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6032    2.2238    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0033    1.9432    2.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1340    0.3677    2.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  1  6
 12 13  2  0
 12 14  1  0
  4 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16  2  1  0
 23 18  1  0
 11  6  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
 23 37  1  0
M  END


  Mrv1652306242107423D          

 37 39  0  0  0  0            999 V2000
   -1.2171    1.5166    0.9674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6819    0.3971    0.7544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018    0.1154    0.8200 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856   -0.9600   -0.0807 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1664   -1.7146    0.1802 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3602   -0.8701    0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8595   -0.1931    1.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9808    0.6134    1.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6297    0.7465   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375    0.0678   -1.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152   -0.7307   -1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7722   -0.4610   -1.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472    0.7400   -1.7461 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9202   -1.3575   -2.5041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -1.7768    0.2775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029   -0.8683    0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591   -1.1567    0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393   -0.2189    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5741   -0.0199   -0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6164    0.8405   -0.5225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7580    1.5417    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8632    1.3782    1.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8057    0.4895    1.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0851   -2.1689    1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -2.5345   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3578   -0.2909    2.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3793    1.1503    1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5181    1.3835   -0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6679    0.1926   -2.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847   -1.2319   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.1594   -3.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8317   -2.1823   -0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4414   -0.5855   -1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3415    0.9890   -1.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6032    2.2238    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0033    1.9432    2.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1340    0.3677    2.3337 H   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 12  1  6  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 16  2  1  0  0  0  0
 23 18  1  0  0  0  0
 11  6  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  7 26  1  0  0  0  0
  8 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  0  0  0  0
 14 31  1  0  0  0  0
 17 32  1  0  0  0  0
 19 33  1  0  0  0  0
 20 34  1  0  0  0  0
 21 35  1  0  0  0  0
 22 36  1  0  0  0  0
 23 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010959

> <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])C1=C([H])C([H])=C([H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O5/c19-16-15(11-13-7-3-1-4-8-13)22-18(23-16,17(20)21)12-14-9-5-2-6-10-14/h1-11H,12H2,(H,20,21)/b15-11+/t18-/m1/s1

> <INCHI_KEY>
OLOMGTHWMBYIQH-UHFFFAOYSA-N

> <FORMULA>
C18H14O5

> <MOLECULAR_WEIGHT>
310.305

> <EXACT_MASS>
310.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
31.371137954017257

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,5E)-2-benzyl-4-oxo-5-(phenylmethylidene)-1,3-dioxolane-2-carboxylic acid

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
4.064938054333333

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.219192635235287

> <JCHEM_PKA_STRONGEST_BASIC>
-5.21529137608768

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
83.13660000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5E)-2-benzyl-4-oxo-5-(phenylmethylidene)-1,3-dioxolane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -1.2171    1.5166    0.9674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6819    0.3971    0.7544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018    0.1154    0.8200 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856   -0.9600   -0.0807 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1664   -1.7146    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3602   -0.8701    0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8595   -0.1931    1.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9808    0.6134    1.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6297    0.7465   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375    0.0678   -1.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152   -0.7307   -1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7722   -0.4610   -1.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472    0.7400   -1.7461 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9202   -1.3575   -2.5041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -1.7768    0.2775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029   -0.8683    0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591   -1.1567    0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393   -0.2189    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5741   -0.0199   -0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6164    0.8405   -0.5225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7580    1.5417    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8632    1.3782    1.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8057    0.4895    1.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0851   -2.1689    1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -2.5345   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3578   -0.2909    2.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3793    1.1503    1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5181    1.3835   -0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6679    0.1926   -2.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847   -1.2319   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.1594   -3.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8317   -2.1823   -0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4414   -0.5855   -1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3415    0.9890   -1.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6032    2.2238    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0033    1.9432    2.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1340    0.3677    2.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
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  4 12  1  6
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  4 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16  2  1  0
 23 18  1  0
 11  6  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
 23 37  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -1.217   1.517   0.967  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.682   0.397   0.754  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.702   0.115   0.820  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.886  -0.960  -0.081  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.166  -1.715   0.180  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.360  -0.870   0.057  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.860  -0.193   1.145  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.981   0.613   1.077  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.630   0.747  -0.135  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.138   0.068  -1.247  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.015  -0.731  -1.148  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.772  -0.461  -1.458  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.547   0.740  -1.746  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.920  -1.357  -2.504  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.226  -1.777   0.278  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.303  -0.868   0.394  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.559  -1.157   0.209  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.639  -0.219   0.342  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.574  -0.020  -0.665  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.616   0.841  -0.523  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.758   1.542   0.655  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.863   1.378   1.673  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.806   0.490   1.499  0.00  0.00           C+0
HETATM   24  H   UNK     0       2.085  -2.169   1.183  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.243  -2.535  -0.546  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.358  -0.291   2.099  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.379   1.150   1.933  0.00  0.00           H+0
HETATM   28  H   UNK     0       6.518   1.383  -0.197  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.668   0.193  -2.181  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.685  -1.232  -2.055  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.687  -1.159  -3.465  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.832  -2.182  -0.066  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.441  -0.586  -1.588  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.341   0.989  -1.316  0.00  0.00           H+0
HETATM   35  H   UNK     0      -6.603   2.224   0.738  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.003   1.943   2.583  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.134   0.368   2.334  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12   15                                             
CONECT    5    4    6   24   25                                             
CONECT    6    5    7   11                                                  
CONECT    7    6    8   26                                                  
CONECT    8    7    9   27                                                  
CONECT    9    8   10   28                                                  
CONECT   10    9   11   29                                                  
CONECT   11   10    6   30                                                  
CONECT   12    4   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   31                                                       
CONECT   15    4   16                                                       
CONECT   16   15   17    2                                                  
CONECT   17   16   18   32                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20   33                                                  
CONECT   20   19   21   34                                                  
CONECT   21   20   22   35                                                  
CONECT   22   21   23   36                                                  
CONECT   23   22   18   37                                                  
CONECT   24    5                                                            
CONECT   25    5                                                            
CONECT   26    7                                                            
CONECT   27    8                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   14                                                            
CONECT   32   17                                                            
CONECT   33   19                                                            
CONECT   34   20                                                            
CONECT   35   21                                                            
CONECT   36   22                                                            
CONECT   37   23                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

RDKit          3D

37 39  0  0  0  0  0  0  0  0999 V2000
   -1.2171    1.5166    0.9674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6819    0.3971    0.7544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018    0.1154    0.8200 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856   -0.9600   -0.0807 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1664   -1.7146    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3602   -0.8701    0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8595   -0.1931    1.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9808    0.6134    1.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6297    0.7465   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375    0.0678   -1.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152   -0.7307   -1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7722   -0.4610   -1.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472    0.7400   -1.7461 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9202   -1.3575   -2.5041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -1.7768    0.2775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029   -0.8683    0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591   -1.1567    0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393   -0.2189    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5741   -0.0199   -0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6164    0.8405   -0.5225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7580    1.5417    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8632    1.3782    1.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8057    0.4895    1.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0851   -2.1689    1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -2.5345   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3578   -0.2909    2.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3793    1.1503    1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5181    1.3835   -0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6679    0.1926   -2.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847   -1.2319   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.1594   -3.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8317   -2.1823   -0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4414   -0.5855   -1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3415    0.9890   -1.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6032    2.2238    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0033    1.9432    2.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1340    0.3677    2.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  1  6
 12 13  2  0
 12 14  1  0
  4 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16  2  1  0
 23 18  1  0
 11  6  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
 23 37  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Phenguignardate	Generator
2-Benzyl-4-oxo-5-(phenylmethylidene)-1,3-dioxolane-2-carboxylate	Generator

Chemical Formula

C₁₈H₁₄O₅

Average Mass

310.3050 Da

Monoisotopic Mass

310.08412 Da

IUPAC Name

(2R,5E)-2-benzyl-4-oxo-5-(phenylmethylidene)-1,3-dioxolane-2-carboxylic acid

Traditional Name

(2R,5E)-2-benzyl-4-oxo-5-(phenylmethylidene)-1,3-dioxolane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1(CC2=CC=CC=C2)OC(=O)C(O1)=CC1=CC=CC=C1

InChI Identifier

InChI=1S/C18H14O5/c19-16-15(11-13-7-3-1-4-8-13)22-18(23-16,17(20)21)12-14-9-5-2-6-10-14/h1-11H,12H2,(H,20,21)

InChI Key

OLOMGTHWMBYIQH-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Guignardia	NPAtlas	22779915
Phyllosticta ampelicida	LOTUS Database	35616633

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	3.64	ALOGPS
logP	4.06	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.22	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	4	ChemAxon
Refractivity	83.14 m³·mol⁻¹	ChemAxon
Polarizability	31.37 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

NPAtlas ID

NPA011282

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

72681011

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Molitor D, Liermann JC, Berkelmann-Lohnertz B, Buckel I, Opatz T, Thines E: Phenguignardic acid and guignardic acid, phytotoxic secondary metabolites from Guignardia bidwellii. J Nat Prod. 2012 Jul 27;75(7):1265-9. doi: 10.1021/np2008945. Epub 2012 Jul 10. [PubMed:22779915 ]

Showing NP-Card for Phenguignardic acid (NP0010959)

MOL for NP0010959 (Phenguignardic acid)

3D MOL for NP0010959 (Phenguignardic acid)

3D SDF for NP0010959 (Phenguignardic acid)

3D-SDF for NP0010959 (Phenguignardic acid)

PDB for NP0010959 (Phenguignardic acid)

3D PDB for NP0010959 (Phenguignardic acid)

SMILES for NP0010959 (Phenguignardic acid)

INCHI for NP0010959 (Phenguignardic acid)

Structure for NP0010959 (Phenguignardic acid)

3D Structure for NP0010959 (Phenguignardic acid)