NP-MRD: Showing NP-Card for 4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid (NP0233255)

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Record Information

Version

2.0

Created at

2022-09-06 14:47:20 UTC

Updated at

2022-09-06 14:47:20 UTC

NP-MRD ID

NP0233255

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid

Description

4-(3-Hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid 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. 4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid is found in Setophoma terrestris. 4-(3-Hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
    1.0431   -3.7431   -0.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732   -2.5092   -0.4314 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0026   -1.2927   -0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3799   -1.2360   -0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9616    0.0312   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4169    0.1475    0.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1331   -0.8885    0.1989 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9881    1.4058    0.2110 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1884    1.1646   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8276    1.1115   -0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0165    2.3337   -0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469   -0.1413   -0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1937   -0.1713   -0.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6002   -0.1586   -1.8095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986   -0.2106    0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1421    0.8766    0.5607 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0269    0.8046   -0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8993    0.7374    1.7346 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3786   -4.5346   -0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949   -3.9730    0.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0029   -3.7030   -0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9747   -2.1304   -0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6344    2.1035   -0.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6218    2.1617   -0.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3230    2.6465    0.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6330    3.1680   -0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9018    2.1743   -1.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5113   -0.2256    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6884   -1.1736    0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7005    1.9035    0.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3945   -0.2084   -0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4217    1.2389   -1.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8640    1.5371   -0.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3190    0.7535    2.5313 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  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  5  6  1  0
  6  8  1  0
  6  7  2  0
 12  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  1
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
  8 23  1  0
M  END


  Mrv1533004161503382D          

 18 18  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
   -0.7145    2.0625    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
   -2.1434    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    2.0625    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 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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233255

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O5/c1-7-4-9(13(16)17)6-11(18-3)12(7)10(15)5-8(2)14/h4,6,8,14H,5H2,1-3H3,(H,16,17)

> <INCHI_KEY>
ISUCSLSQOIOUHP-UHFFFAOYSA-N

> <FORMULA>
C13H16O5

> <MOLECULAR_WEIGHT>
252.266

> <EXACT_MASS>
252.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.163368317321734

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.380566081333333

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.959127842051895

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.573560268363878

> <JCHEM_PKA_STRONGEST_BASIC>
-2.589239770849529

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
66.04180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-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      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   18  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   16                                                  
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   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    5   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
4-(3-Hydroxybutanoyl)-3-methoxy-5-methylbenzoate	Generator

Chemical Formula

C₁₃H₁₆O₅

Average Mass

252.2660 Da

Monoisotopic Mass

252.09977 Da

IUPAC Name

4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid

Traditional Name

4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(C)=C1C(=O)CC(C)O)C(O)=O

InChI Identifier

InChI=1S/C13H16O5/c1-7-4-9(13(16)17)6-11(18-3)12(7)10(15)5-8(2)14/h4,6,8,14H,5H2,1-3H3,(H,16,17)

InChI Key

ISUCSLSQOIOUHP-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
Setophoma terrestris	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Butyrophenone
M-methoxybenzoic acid or derivatives
Benzoic acid or derivatives
Benzoic acid
Anisole
Phenoxy compound
Benzoyl
Methoxybenzene
Phenol ether
Aryl alkyl ketone
Toluene
Alkyl aryl ether
Beta-hydroxy ketone
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Ether
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.03	ALOGPS
logP	1.38	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.57	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	66.04 m³·mol⁻¹	ChemAxon
Polarizability	26.16 Å³	ChemAxon
Number of Rings	1	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

LOTUS database [Link]

Showing NP-Card for 4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid (NP0233255)

MOL for NP0233255 (4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid)

3D MOL for NP0233255 (4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid)

3D SDF for NP0233255 (4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid)

3D-SDF for NP0233255 (4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid)

PDB for NP0233255 (4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid)

3D PDB for NP0233255 (4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid)

SMILES for NP0233255 (4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid)

INCHI for NP0233255 (4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid)

Structure for NP0233255 (4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid)

3D Structure for NP0233255 (4-(3-hydroxybutanoyl)-3-methoxy-5-methylbenzoic acid)