NP-MRD: Showing NP-Card for 2-benzyl-4,6-dihydroxybenzoic acid (NP0305455)

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Record Information

Version

2.0

Created at

2022-09-10 21:18:38 UTC

Updated at

2022-09-10 21:18:38 UTC

NP-MRD ID

NP0305455

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-benzyl-4,6-dihydroxybenzoic acid

Description

2-Benzyl-4,6-dihydroxybenzoic acid belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. 2-benzyl-4,6-dihydroxybenzoic acid is found in Senna obtusifolia. 2-Benzyl-4,6-dihydroxybenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
   -0.9005   -2.0075   -2.0592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6832   -1.6062   -1.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7765   -2.4723   -0.9573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6366   -0.3759   -0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6525   -0.1030    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6388   -1.0822    0.6759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6971    1.0634    1.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7278    2.0259    1.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822    3.2120    1.7832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7188    1.8024    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6888    0.5986   -0.5795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5065    0.4054   -1.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6663   -0.1743   -0.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5245    0.7102    0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6174    0.3069    0.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9219   -1.0280    0.8042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1185   -1.9107    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9938   -1.4904   -0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6547   -2.3253   -1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3640   -0.8760    1.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5013    1.2528    1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2995    3.9858    1.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0466    2.5535    0.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542   -0.1639   -2.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8366    1.4275   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3057    1.7542   -0.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2535    1.0426    1.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7985   -1.2953    1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3567   -2.9670    0.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217   -2.2634   -1.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11  4  1  0
 18 13  1  0
  3 19  1  0
  6 20  1  0
  7 21  1  0
  9 22  1  0
 10 23  1  0
 12 24  1  0
 12 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
M  END


  Mrv1533004251505162D          

 18 19  0  0  0  0            999 V2000
    2.8579    0.0000    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
    1.4289    0.0000    0.0000 O   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
    1.4289   -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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0305455

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=C(O)C=C(O)C=C1CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O4/c15-11-7-10(6-9-4-2-1-3-5-9)13(14(17)18)12(16)8-11/h1-5,7-8,15-16H,6H2,(H,17,18)

> <INCHI_KEY>
JJZORPAULBCJKE-UHFFFAOYSA-N

> <FORMULA>
C14H12O4

> <MOLECULAR_WEIGHT>
244.246

> <EXACT_MASS>
244.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
24.28041143778828

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-benzyl-4,6-dihydroxybenzoic acid

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
3.7654921076666668

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.83878778189231

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8639456494084574

> <JCHEM_PKA_STRONGEST_BASIC>
-5.7685232578178836

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
67.01320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-benzyl-4,6-dihydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -3.080   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  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
2-Benzyl-4,6-dihydroxybenzoate	Generator

Chemical Formula

C₁₄H₁₂O₄

Average Mass

244.2460 Da

Monoisotopic Mass

244.07356 Da

IUPAC Name

2-benzyl-4,6-dihydroxybenzoic acid

Traditional Name

2-benzyl-4,6-dihydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=C(O)C=C(O)C=C1CC1=CC=CC=C1

InChI Identifier

InChI=1S/C14H12O4/c15-11-7-10(6-9-4-2-1-3-5-9)13(14(17)18)12(16)8-11/h1-5,7-8,15-16H,6H2,(H,17,18)

InChI Key

JJZORPAULBCJKE-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
Senna obtusifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Dihydroxybenzoic acid
Salicylic acid
Salicylic acid or derivatives
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Benzoyl
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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	2.95	ALOGPS
logP	3.77	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.86	ChemAxon
pKa (Strongest Basic)	-5.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	67.01 m³·mol⁻¹	ChemAxon
Polarizability	24.28 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

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 2-benzyl-4,6-dihydroxybenzoic acid (NP0305455)

MOL for NP0305455 (2-benzyl-4,6-dihydroxybenzoic acid)

3D MOL for NP0305455 (2-benzyl-4,6-dihydroxybenzoic acid)

3D SDF for NP0305455 (2-benzyl-4,6-dihydroxybenzoic acid)

3D-SDF for NP0305455 (2-benzyl-4,6-dihydroxybenzoic acid)

PDB for NP0305455 (2-benzyl-4,6-dihydroxybenzoic acid)

3D PDB for NP0305455 (2-benzyl-4,6-dihydroxybenzoic acid)

SMILES for NP0305455 (2-benzyl-4,6-dihydroxybenzoic acid)

INCHI for NP0305455 (2-benzyl-4,6-dihydroxybenzoic acid)

Structure for NP0305455 (2-benzyl-4,6-dihydroxybenzoic acid)

3D Structure for NP0305455 (2-benzyl-4,6-dihydroxybenzoic acid)