NP-MRD: Showing NP-Card for truxillic acid (NP0219749)

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Record Information

Version

1.0

Created at

2022-09-05 20:51:00 UTC

Updated at

2022-09-05 20:51:00 UTC

NP-MRD ID

NP0219749

Secondary Accession Numbers

None

Natural Product Identification

Common Name

truxillic acid

Description

Truxillic acid, also known as truxillate, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. These compounds are obtained by the [2 + 2] photocycloadditions of cinnamic acid where the two trans alkenes react head-to-tail. These compounds are found in a variety of plants, for example in coca. Truxillic acid is a weakly acidic compound (based on its pKa). Incarvillateine, an alkaloid from the plant Incarvillea sinensis, is a derivative of α-truxillic acid. They are colorless solids. Truxillic acids are any of several crystalline stereoisomeric cyclic dicarboxylic acids with the formula (C6H5)2C4H4(COOH)2. The isolated stereoisomers are called truxillic acids. Upon heating, truxillic acids undergo cracking to give cinnamic acid. Truxillic acid can exist in five isomers.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161513592D          

 22 24  0  0  0  0            999 V2000
    0.0000   -0.0000    0.0000 O   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
    1.4289   -0.0000    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
    1.2978   -1.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311   -1.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6939   -1.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1064   -2.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314   -2.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3439   -1.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314   -1.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1064   -1.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1228   -1.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5353   -1.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603   -1.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7728   -1.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603   -2.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5353   -2.5353    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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  4  7  1  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219749

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1C(C(C1C1=CC=CC=C1)C(O)=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O4/c19-17(20)15-13(11-7-3-1-4-8-11)16(18(21)22)14(15)12-9-5-2-6-10-12/h1-10,13-16H,(H,19,20)(H,21,22)

> <INCHI_KEY>
QWFRRFLKWRIKSZ-UHFFFAOYSA-N

> <FORMULA>
C18H16O4

> <MOLECULAR_WEIGHT>
296.322

> <EXACT_MASS>
296.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.190859571965596

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4-diphenylcyclobutane-1,3-dicarboxylic acid

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
3.0654098246666663

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.698094828759712

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.010148976531192

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
80.17100000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
truxillic 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  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.423  -3.399   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -4.488   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.245  -3.399   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.295  -3.399   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.065  -4.733   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.605  -4.733   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.375  -3.399   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.605  -2.065   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.065  -2.065   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -6.028   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000  -6.798   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667  -6.798   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.963  -3.399   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.733  -2.065   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.273  -2.065   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.043  -3.399   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.273  -4.733   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.733  -4.733   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    7                                                  
CONECT    5    4    6   17                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    4    8                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    6   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    5   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Truxillate	Generator
Truxillic acid, (1alpha,2alpha,3beta,4beta)-isomer	MeSH
2,4-Diphenylcyclobutane-1,3-dicarboxylate	Generator

Chemical Formula

C₁₈H₁₆O₄

Average Mass

296.3220 Da

Monoisotopic Mass

296.10486 Da

IUPAC Name

2,4-diphenylcyclobutane-1,3-dicarboxylic acid

Traditional Name

truxillic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1C(C(C1C1=CC=CC=C1)C(O)=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H16O4/c19-17(20)15-13(11-7-3-1-4-8-11)16(18(21)22)14(15)12-9-5-2-6-10-12/h1-10,13-16H,(H,19,20)(H,21,22)

InChI Key

QWFRRFLKWRIKSZ-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.78	ALOGPS
logP	3.07	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.01	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.17 m³·mol⁻¹	ChemAxon
Polarizability	30.19 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

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

Truxillic acid

METLIN ID

Not Available

PubChem Compound

78213

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for truxillic acid (NP0219749)

MOL for NP0219749 (truxillic acid)

3D MOL for NP0219749 (truxillic acid)

3D SDF for NP0219749 (truxillic acid)

3D-SDF for NP0219749 (truxillic acid)

PDB for NP0219749 (truxillic acid)

3D PDB for NP0219749 (truxillic acid)

SMILES for NP0219749 (truxillic acid)

INCHI for NP0219749 (truxillic acid)

Structure for NP0219749 (truxillic acid)

3D Structure for NP0219749 (truxillic acid)