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Showing NP-Card for macrophomic acid (NP0298021)

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Record Information
Version2.0
Created at2022-09-10 08:54:05 UTC
Updated at2022-09-10 08:54:05 UTC
NP-MRD IDNP0298021
Secondary Accession NumbersNone
Natural Product Identification
Common Namemacrophomic acid
DescriptionMacrophomic acid, also known as macrophomate, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Macrophomic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). macrophomic acid is found in Macrophoma commelinae. A methoxybenzoic acid having a single methoxy group at the 3-position together with acetyl and methyl substituents at the 4- and 5-positions respectively.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0298021 (macrophomic acid)


  Mrv1533004241500352D          

 15 15  0  0  0  0            999 V2000
    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 O   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
    1.4289    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
   -0.7145   -0.4125    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
Download

3D MOL for NP0298021 (macrophomic acid)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
   -1.0389    3.2477    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3873    1.8800    0.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067    0.9233    0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8865    1.3119    0.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9384    0.4287   -0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2957    0.8899   -0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5539    2.1091   -0.3374 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3283   -0.0074   -0.4659 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -0.9172   -0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3036   -1.3327    0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0354   -2.7767    0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7114   -0.4178    0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0632   -0.8817    0.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9493   -1.1135   -0.6473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4875   -1.0887    1.6725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3577    3.4875    1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4835    3.5132   -0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9460    3.8848    0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1496    2.3724    0.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1898   -0.8782   -0.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4213   -1.6206   -0.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6663   -3.3847   -0.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1117   -3.0950    1.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1012   -2.9470   -0.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6440   -0.2696   -0.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4550   -2.0895   -0.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3823   -1.2283   -1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  5  6  1  0
  6  8  1  0
  6  7  2  0
 12  3  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  9 21  1  0
 11 22  1  0
 11 23  1  0
 11 24  1  0
 14 25  1  0
 14 26  1  0
 14 27  1  0
  8 20  1  0
M  END
Download

3D SDF for NP0298021 (macrophomic acid)


  Mrv1533004241500352D          

 15 15  0  0  0  0            999 V2000
    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 O   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
    1.4289    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
   -0.7145   -0.4125    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0298021

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(C)=C1C(C)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O4/c1-6-4-8(11(13)14)5-9(15-3)10(6)7(2)12/h4-5H,1-3H3,(H,13,14)

> <INCHI_KEY>
GWSISRLRTQOQNE-UHFFFAOYSA-N

> <FORMULA>
C11H12O4

> <MOLECULAR_WEIGHT>
208.213

> <EXACT_MASS>
208.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.11727311627439

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-acetyl-3-methoxy-5-methylbenzoic acid

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
1.5442263663333329

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.850479697750345

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5839257531286575

> <JCHEM_PKA_STRONGEST_BASIC>
-4.881277990651605

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
55.22140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
macrophomic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0298021 (macrophomic acid)

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PDB for NP0298021 (macrophomic acid)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    5   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

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3D PDB for NP0298021 (macrophomic acid)
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SMILES for NP0298021 (macrophomic acid)
COC1=CC(=CC(C)=C1C(C)=O)C(O)=O
Download
INCHI for NP0298021 (macrophomic acid)
InChI=1S/C11H12O4/c1-6-4-8(11(13)14)5-9(15-3)10(6)7(2)12/h4-5H,1-3H3,(H,13,14)
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View in JSmol
Synonyms
ValueSource
MacrophomateGenerator
Chemical FormulaC11H12O4
Average Mass208.2130 Da
Monoisotopic Mass208.07356 Da
IUPAC Name4-acetyl-3-methoxy-5-methylbenzoic acid
Traditional Namemacrophomic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC(C)=C1C(C)=O)C(O)=O
InChI Identifier
InChI=1S/C11H12O4/c1-6-4-8(11(13)14)5-9(15-3)10(6)7(2)12/h4-5H,1-3H3,(H,13,14)
InChI KeyGWSISRLRTQOQNE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Macrophoma commelinaeLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAlkyl-phenylketones  
Alternative Parents
Substituents
  • Alkyl-phenylketone
    • 

  • M-methoxybenzoic acid or derivatives
    • 

  • Acetophenone
    • 

  • Benzoic acid or derivatives
    • 

  • Benzoic acid
    • 

  • Aryl alkyl ketone
    • 

  • Phenol ether
    • 

  • Methoxybenzene
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Benzoyl
    • 

  • Toluene
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.5ALOGPS
logP1.54ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.58ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity55.22 m³·mol⁻¹ChemAxon
Polarizability21.12 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMacrophomic acid  
METLIN IDNot Available
PubChem Compound10889109  
PDB IDNot Available
ChEBI ID38227  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]