NP-MRD: Showing NP-Card for Anacardic acid (NP0047779)

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Record Information

Version

2.0

Created at

2022-03-17 20:45:49 UTC

Updated at

2022-03-17 20:45:49 UTC

NP-MRD ID

NP0047779

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Anacardic acid

Description

Anacardic acid, also known as anacardate, belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. Anacardic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Anacardic acid has been detected, but not quantified in, a few different foods, such as cashew nuts, ginkgo nuts, and nuts. This could make anacardic acid a potential biomarker for the consumption of these foods. Anacardic acids are chemical compounds found in the shell of the cashew nut (Anacardium occidentale). The exact mixture depends on the species of the plant and the major component is C5:3 All-Z. Chemically, anacardic acid is a mixture of several closely related organic compounds. Anacardic acid is found in Amphipterygium adstringens, Rhus javanica , Ozoroa mucronata, Philodendron scandens , Pistacia vera and Scrophularia californica. Anacardic acid was first documented in 2007 (PMID: 17601740). Each consists of a salicylic acid substituted with an alkyl chain that has 15 or 17 carbon atoms; anacardic acid is a mixture of saturated and unsaturated molecules.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241218392D          

 25 25  0  0  0  0            999 V2000
   -1.5616   -6.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2761   -7.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2761   -8.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616   -8.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8471   -8.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9905   -6.8357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616   -6.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8471   -5.5982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2761   -5.5982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8471   -7.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1327   -6.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5818   -7.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2963   -6.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0107   -7.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7252   -6.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4397   -7.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -6.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8686   -7.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5831   -6.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5831   -6.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2976   -5.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2976   -4.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5831   -4.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5831   -3.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8686   -3.1232    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5 10  1  0  0  0  0
  1 10  2  0  0  0  0
  2  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  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  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047779

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC\C=C/C\C=C/CCCCCCCC1=C(C(O)=O)C(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h4-5,7-8,15,17-18,23H,2-3,6,9-14,16H2,1H3,(H,24,25)/b5-4-,8-7-

> <INCHI_KEY>
KAOMOVYHGLSFHQ-UTOQUPLUSA-N

> <FORMULA>
C22H32O3

> <MOLECULAR_WEIGHT>
344.4877

> <EXACT_MASS>
344.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
41.230795155602614

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzoic acid

> <ALOGPS_LOGP>
7.28

> <JCHEM_LOGP>
7.990802788333333

> <ALOGPS_LOGS>
-5.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.364273313389209

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6407335510780507

> <JCHEM_PKA_STRONGEST_BASIC>
-6.287065354678508

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
106.9835

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.03e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.915 -12.760   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.249 -13.530   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.249 -15.070   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.915 -15.840   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.581 -15.070   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.582 -12.760   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.915 -11.220   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.581 -10.450   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -4.249 -10.450   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.581 -13.530   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.248 -12.760   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.086 -13.530   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.420 -12.760   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.753 -13.530   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.087 -12.760   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.421 -13.530   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.755 -12.760   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.088 -13.530   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.422 -12.760   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.422 -11.220   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.756 -10.450   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.756  -8.910   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.422  -8.140   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.422  -6.600   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.088  -5.830   0.000  0.00  0.00           C+0
CONECT    1    2   10    7                                                  
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4   10                                                       
CONECT    6    2                                                            
CONECT    7    1    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5    1   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Value	Source
Anacardate	Generator
(15:2)-Anacardic acid	HMDB
2-Hydroxy-6-(8,11-pentadecadienyl)-(Z,Z)-benzoic acid	HMDB
2-Hydroxy-6-(8Z,11Z)-8,11-pentadecadien-1-yl-benzoic acid	HMDB
Anacardic acid diene	HMDB
2-Hydroxy-6-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzoate	Generator

Chemical Formula

C₂₂H₃₂O₃

Average Mass

344.4877 Da

Monoisotopic Mass

344.23514 Da

IUPAC Name

2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzoic acid

Traditional Name

2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzoic acid

CAS Registry Number

103904-74-1

SMILES

CCC\C=C/C\C=C/CCCCCCCC1=C(C(O)=O)C(O)=CC=C1

InChI Identifier

InChI=1S/C22H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h4-5,7-8,15,17-18,23H,2-3,6,9-14,16H2,1H3,(H,24,25)/b5-4-,8-7-

InChI Key

KAOMOVYHGLSFHQ-UTOQUPLUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amphipterygium adstringens	Plant	KNApSAcK
Anacardium occidentale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brucea javanica	Plant	KNApSAcK
Ginkgo biloba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ozoroa mucronata	Plant	KNApSAcK
Philodendron scandens	Plant	KNApSAcK
Pistacia vera	Plant	KNApSAcK
Scrophularia californica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylic acids

Alternative Parents

Substituents

Salicylic acid
Benzoic acid
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	7.28	ALOGPS
logP	7.99	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	2.64	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	106.98 m³·mol⁻¹	ChemAxon
Polarizability	41.23 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033896

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012091

KNApSAcK ID

Not Available

Chemspider ID

9998782

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Anacardic acids

METLIN ID

Not Available

PubChem Compound

11824131

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Green IR, Tocoli FE, Lee SH, Nihei K, Kubo I: Molecular design of anti-MRSA agents based on the anacardic acid scaffold. Bioorg Med Chem. 2007 Sep 15;15(18):6236-41. doi: 10.1016/j.bmc.2007.06.022. Epub 2007 Jun 14. [PubMed:17601740 ]

Showing NP-Card for Anacardic acid (NP0047779)

MOL for NP0047779 (Anacardic acid)

3D MOL for NP0047779 (Anacardic acid)

3D SDF for NP0047779 (Anacardic acid)

3D-SDF for NP0047779 (Anacardic acid)

PDB for NP0047779 (Anacardic acid)

3D PDB for NP0047779 (Anacardic acid)

SMILES for NP0047779 (Anacardic acid)

INCHI for NP0047779 (Anacardic acid)

Structure for NP0047779 (Anacardic acid)

3D Structure for NP0047779 (Anacardic acid)