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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 18:40:13 UTC

Update Date

2022-03-07 02:53:53 UTC

HMDB ID

HMDB0033896

Secondary Accession Numbers

HMDB33896

Metabolite Identification

Common Name

Anacardic acid

Description

Anacardic acid is found in cashew nut. Anacardic acid is found in cashew nut shell.Anacardic acids are chemical compounds found in the shell of the cashew nut (Anacardium occidentale). Chemically, anacardic acid is a mixture of several closely related organic compounds. 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. The exact mixture depends on the species of the plant and the major component is C5:3 all-Z. (Wikipedia

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0033896
     RDKit          3D
Anacardic acid
 57 57  0  0  0  0  0  0  0  0999 V2000
    7.5130   -2.7605   -2.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8312   -1.4062   -2.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3135   -1.6224   -2.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5909   -0.3544   -2.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8574    0.1100   -1.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6653   -0.6186    0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1295    0.1715    1.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3219    0.5061    2.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051    0.1481    2.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    1.3938    2.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4219    1.1003    2.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8621    0.3129    1.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3618   -0.0039    1.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1453    1.3008    1.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6289    1.0416    1.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1506    0.3023    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3013   -1.0926    0.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7360   -1.8456   -0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0337   -1.2705   -1.9857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8915    0.1184   -2.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2096    0.5917   -3.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4522    0.8626   -1.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3562    2.2908   -1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9768    3.0493   -0.3172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6829    2.8881   -2.4221 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8354   -3.5799   -1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8945   -3.0169   -3.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4037   -2.6910   -1.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1991   -0.7373   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0464   -0.8914   -3.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0507   -2.1334   -3.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0617   -2.3559   -1.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6976    0.2429   -2.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    1.0816   -1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6017   -0.9043    0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2136   -1.5812    0.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1977    0.4846    1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7116    1.1065    3.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5502   -0.6581    1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7611   -0.2636    3.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274    1.9859    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047    2.0033    3.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7349    0.5855    3.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9477    2.0995    2.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6809    0.9909    0.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2774   -0.5911    1.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707   -0.5877    0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5689   -0.5474    2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7744    1.9989    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9244    1.7673    2.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7782    0.3732    2.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1499    1.9601    1.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0770   -1.5643    1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8601   -2.9339   -0.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3794   -1.8882   -2.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2481    1.4031   -3.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1032    3.6288   -2.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 21 56  1  0
 25 57  1  0
M  END


  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>
HMDB0033896

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0033896
     RDKit          3D
Anacardic acid
 57 57  0  0  0  0  0  0  0  0999 V2000
    7.5130   -2.7605   -2.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8312   -1.4062   -2.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3135   -1.6224   -2.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5909   -0.3544   -2.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8574    0.1100   -1.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6653   -0.6186    0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1295    0.1715    1.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3219    0.5061    2.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051    0.1481    2.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    1.3938    2.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4219    1.1003    2.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8621    0.3129    1.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3618   -0.0039    1.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1453    1.3008    1.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6289    1.0416    1.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1506    0.3023    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3013   -1.0926    0.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7360   -1.8456   -0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0337   -1.2705   -1.9857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8915    0.1184   -2.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2096    0.5917   -3.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4522    0.8626   -1.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3562    2.2908   -1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9768    3.0493   -0.3172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6829    2.8881   -2.4221 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8354   -3.5799   -1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8945   -3.0169   -3.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4037   -2.6910   -1.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1991   -0.7373   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0464   -0.8914   -3.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0507   -2.1334   -3.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0617   -2.3559   -1.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6976    0.2429   -2.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    1.0816   -1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6017   -0.9043    0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2136   -1.5812    0.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1977    0.4846    1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7116    1.1065    3.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5502   -0.6581    1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7611   -0.2636    3.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274    1.9859    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047    2.0033    3.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7349    0.5855    3.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9477    2.0995    2.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6809    0.9909    0.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2774   -0.5911    1.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707   -0.5877    0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5689   -0.5474    2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7744    1.9989    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9244    1.7673    2.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7782    0.3732    2.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1499    1.9601    1.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0770   -1.5643    1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8601   -2.9339   -0.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3794   -1.8882   -2.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2481    1.4031   -3.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1032    3.6288   -2.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 21 56  1  0
 25 57  1  0
M  END

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

COMPND    HMDB0033896
HETATM    1  C1  UNL     1       7.513  -2.761  -2.136  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.831  -1.406  -2.177  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.313  -1.622  -2.024  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.591  -0.354  -2.057  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.857   0.110  -1.101  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.665  -0.619   0.176  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.129   0.172   1.334  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.322   0.506   2.302  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.905   0.148   2.355  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.034   1.394   2.376  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.422   1.100   2.435  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.862   0.313   1.231  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.362  -0.004   1.261  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.145   1.301   1.283  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.629   1.042   1.300  1.00  0.00           C  
HETATM   16  C16 UNL     1      -5.151   0.302   0.158  1.00  0.00           C  
HETATM   17  C17 UNL     1      -5.301  -1.093   0.287  1.00  0.00           C  
HETATM   18  C18 UNL     1      -5.736  -1.846  -0.778  1.00  0.00           C  
HETATM   19  C19 UNL     1      -6.034  -1.271  -1.986  1.00  0.00           C  
HETATM   20  C20 UNL     1      -5.891   0.118  -2.136  1.00  0.00           C  
HETATM   21  O1  UNL     1      -6.210   0.592  -3.368  1.00  0.00           O  
HETATM   22  C21 UNL     1      -5.452   0.863  -1.048  1.00  0.00           C  
HETATM   23  C22 UNL     1      -5.356   2.291  -1.226  1.00  0.00           C  
HETATM   24  O2  UNL     1      -4.977   3.049  -0.317  1.00  0.00           O  
HETATM   25  O3  UNL     1      -5.683   2.888  -2.422  1.00  0.00           O  
HETATM   26  H1  UNL     1       6.835  -3.580  -1.858  1.00  0.00           H  
HETATM   27  H2  UNL     1       7.894  -3.017  -3.161  1.00  0.00           H  
HETATM   28  H3  UNL     1       8.404  -2.691  -1.484  1.00  0.00           H  
HETATM   29  H4  UNL     1       7.199  -0.737  -1.369  1.00  0.00           H  
HETATM   30  H5  UNL     1       7.046  -0.891  -3.136  1.00  0.00           H  
HETATM   31  H6  UNL     1       5.051  -2.133  -3.016  1.00  0.00           H  
HETATM   32  H7  UNL     1       5.062  -2.356  -1.281  1.00  0.00           H  
HETATM   33  H8  UNL     1       4.698   0.243  -2.996  1.00  0.00           H  
HETATM   34  H9  UNL     1       3.367   1.082  -1.258  1.00  0.00           H  
HETATM   35  H10 UNL     1       2.602  -0.904   0.193  1.00  0.00           H  
HETATM   36  H11 UNL     1       4.214  -1.581   0.238  1.00  0.00           H  
HETATM   37  H12 UNL     1       5.198   0.485   1.372  1.00  0.00           H  
HETATM   38  H13 UNL     1       3.712   1.107   3.162  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.550  -0.658   1.739  1.00  0.00           H  
HETATM   40  H15 UNL     1       1.761  -0.264   3.426  1.00  0.00           H  
HETATM   41  H16 UNL     1       1.227   1.986   1.453  1.00  0.00           H  
HETATM   42  H17 UNL     1       1.305   2.003   3.282  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.735   0.585   3.369  1.00  0.00           H  
HETATM   44  H19 UNL     1      -0.948   2.100   2.359  1.00  0.00           H  
HETATM   45  H20 UNL     1      -0.681   0.991   0.351  1.00  0.00           H  
HETATM   46  H21 UNL     1      -0.277  -0.591   1.035  1.00  0.00           H  
HETATM   47  H22 UNL     1      -2.571  -0.588   0.356  1.00  0.00           H  
HETATM   48  H23 UNL     1      -2.569  -0.547   2.184  1.00  0.00           H  
HETATM   49  H24 UNL     1      -2.774   1.999   0.530  1.00  0.00           H  
HETATM   50  H25 UNL     1      -2.924   1.767   2.290  1.00  0.00           H  
HETATM   51  H26 UNL     1      -4.778   0.373   2.225  1.00  0.00           H  
HETATM   52  H27 UNL     1      -5.150   1.960   1.583  1.00  0.00           H  
HETATM   53  H28 UNL     1      -5.077  -1.564   1.213  1.00  0.00           H  
HETATM   54  H29 UNL     1      -5.860  -2.934  -0.696  1.00  0.00           H  
HETATM   55  H30 UNL     1      -6.379  -1.888  -2.826  1.00  0.00           H  
HETATM   56  H31 UNL     1      -6.248   1.403  -3.853  1.00  0.00           H  
HETATM   57  H32 UNL     1      -5.103   3.629  -2.843  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5    5   33
CONECT    5    6   34
CONECT    6    7   35   36
CONECT    7    8    8   37
CONECT    8    9   38
CONECT    9   10   39   40
CONECT   10   11   41   42
CONECT   11   12   43   44
CONECT   12   13   45   46
CONECT   13   14   47   48
CONECT   14   15   49   50
CONECT   15   16   51   52
CONECT   16   17   17   22
CONECT   17   18   53
CONECT   18   19   19   54
CONECT   19   20   55
CONECT   20   21   22   22
CONECT   21   56
CONECT   22   23
CONECT   23   24   24   25
CONECT   25   57
END

HMDB0033896
     RDKit          3D
Anacardic acid
 57 57  0  0  0  0  0  0  0  0999 V2000
    7.5130   -2.7605   -2.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8312   -1.4062   -2.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3135   -1.6224   -2.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5909   -0.3544   -2.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8574    0.1100   -1.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6653   -0.6186    0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1295    0.1715    1.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3219    0.5061    2.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051    0.1481    2.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    1.3938    2.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4219    1.1003    2.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8621    0.3129    1.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3618   -0.0039    1.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1453    1.3008    1.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6289    1.0416    1.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1506    0.3023    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3013   -1.0926    0.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7360   -1.8456   -0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0337   -1.2705   -1.9857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8915    0.1184   -2.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2096    0.5917   -3.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4522    0.8626   -1.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3562    2.2908   -1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9768    3.0493   -0.3172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6829    2.8881   -2.4221 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8354   -3.5799   -1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8945   -3.0169   -3.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4037   -2.6910   -1.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1991   -0.7373   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0464   -0.8914   -3.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0507   -2.1334   -3.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0617   -2.3559   -1.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6976    0.2429   -2.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    1.0816   -1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6017   -0.9043    0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2136   -1.5812    0.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1977    0.4846    1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7116    1.1065    3.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5502   -0.6581    1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7611   -0.2636    3.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274    1.9859    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047    2.0033    3.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7349    0.5855    3.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9477    2.0995    2.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6809    0.9909    0.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2774   -0.5911    1.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707   -0.5877    0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5689   -0.5474    2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7744    1.9989    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9244    1.7673    2.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7782    0.3732    2.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1499    1.9601    1.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0770   -1.5643    1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8601   -2.9339   -0.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3794   -1.8882   -2.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2481    1.4031   -3.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1032    3.6288   -2.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 21 56  1  0
 25 57  1  0
M  END

View in JSmol View Stereo Labels

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 Molecular Weight

344.4877

Monoisotopic Molecular Weight

344.23514489

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

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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033896)
Cell membrane (HMDB: HMDB0033896)

Excreta

Biofluid or Excreta

Feces (PMID: 28923537)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033896)

Source

Exogenous

Exogenous (HMDB: HMDB0033896)

Food

Food (HMDB: HMDB0033896)

Nut

Cashew nut (FooDB: FOOD00011)
Nuts (FooDB: FOOD00869)

Herb and spice

Other seed

Ginkgo nuts (FooDB: FOOD00367)

Endogenous

Plant

Plant (HMDB: HMDB0033896)

Not Available

Lipoxygenase inhibitor (HMDB: HMDB0033896)
Prostaglandin-synthetase inhibitor (HMDB: HMDB0033896)

EC 1.14.18.1 (tyrosinase) inhibitor (HMDB: HMDB0033896)

Industrial application

Agriculture

Pesticide

Pesticide (HMDB: HMDB0033896)

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0033896)

Molluscicide (HMDB: HMDB0033896)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	25 - 26 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0004 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	190.33	31661259
DarkChem	[M-H]-	189.038	31661259
DeepCCS	[M+H]+	193.48	30932474
DeepCCS	[M-H]-	190.395	30932474
DeepCCS	[M-2H]-	225.628	30932474
DeepCCS	[M+Na]+	201.918	30932474
AllCCS	[M+H]+	192.6	32859911
AllCCS	[M+H-H2O]+	189.8	32859911
AllCCS	[M+NH4]+	195.2	32859911
AllCCS	[M+Na]+	196.0	32859911
AllCCS	[M-H]-	192.7	32859911
AllCCS	[M+Na-2H]-	194.3	32859911
AllCCS	[M+HCOO]-	196.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	10.42 minutes	32390414
Predicted by Siyang on May 30, 2022	26.0507 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.16 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	36.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3498.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	692.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	278.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	433.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	734.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1294.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1003.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	98.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2416.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	845.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2146.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	878.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	610.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	536.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	619.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Anacardic acid	CCC\C=C/C\C=C/CCCCCCCC1=C(C(O)=O)C(O)=CC=C1	3903.8	Standard polar	33892256
Anacardic acid	CCC\C=C/C\C=C/CCCCCCCC1=C(C(O)=O)C(O)=CC=C1	2674.5	Standard non polar	33892256
Anacardic acid	CCC\C=C/C\C=C/CCCCCCCC1=C(C(O)=O)C(O)=CC=C1	2817.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Anacardic acid,1TMS,isomer #1	CCC/C=C\C/C=C\CCCCCCCC1=CC=CC(O)=C1C(=O)O[Si](C)(C)C	2761.9	Semi standard non polar	33892256
Anacardic acid,1TMS,isomer #2	CCC/C=C\C/C=C\CCCCCCCC1=CC=CC(O[Si](C)(C)C)=C1C(=O)O	2857.1	Semi standard non polar	33892256
Anacardic acid,2TMS,isomer #1	CCC/C=C\C/C=C\CCCCCCCC1=CC=CC(O[Si](C)(C)C)=C1C(=O)O[Si](C)(C)C	2831.6	Semi standard non polar	33892256
Anacardic acid,1TBDMS,isomer #1	CCC/C=C\C/C=C\CCCCCCCC1=CC=CC(O)=C1C(=O)O[Si](C)(C)C(C)(C)C	3001.8	Semi standard non polar	33892256
Anacardic acid,1TBDMS,isomer #2	CCC/C=C\C/C=C\CCCCCCCC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)O	3102.6	Semi standard non polar	33892256
Anacardic acid,2TBDMS,isomer #1	CCC/C=C\C/C=C\CCCCCCCC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)O[Si](C)(C)C(C)(C)C	3275.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Anacardic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-2921000000-e8cfe2a19fc08dd61fc4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anacardic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00di-4704900000-312b95cecb769b1cc38f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anacardic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Anacardic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anacardic acid 10V, Positive-QTOF	splash10-0002-1029000000-1c006ff8be091bc98439	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anacardic acid 20V, Positive-QTOF	splash10-0f6t-7956000000-3946fdbefd02d9f18e6b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anacardic acid 40V, Positive-QTOF	splash10-0006-3920000000-e4c2c005a187b27cba9e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anacardic acid 10V, Negative-QTOF	splash10-0007-0069000000-8dec51893da3aa8bc11f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anacardic acid 20V, Negative-QTOF	splash10-0002-0092000000-72c001bfc57b828f48f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anacardic acid 40V, Negative-QTOF	splash10-0002-1290000000-f2c31a6187b07fac82de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anacardic acid 10V, Positive-QTOF	splash10-0002-0119000000-8309caef0bfe8a677975	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anacardic acid 20V, Positive-QTOF	splash10-052b-4595000000-398d788100a917a69a30	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anacardic acid 40V, Positive-QTOF	splash10-0693-9500000000-37e1dd3de2033d9d0adf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anacardic acid 10V, Negative-QTOF	splash10-0006-0019000000-eabf76621e8dfe5f7a8a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anacardic acid 20V, Negative-QTOF	splash10-0002-0294000000-7a525af1df4de6d1df18	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Anacardic acid 40V, Negative-QTOF	splash10-0596-3960000000-7d0a6e1a243cf5f3d32f	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Metastatic melanoma	28923537	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Metastatic melanoma
Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012091

KNApSAcK ID

C00002635

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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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. Epub 2007 Jun 14. [PubMed:17601740 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Anacardic acid (HMDB0033896)

MOL for HMDB0033896 (Anacardic acid)

3D MOL for HMDB0033896 (Anacardic acid)

3D SDF for HMDB0033896 (Anacardic acid)

3D-SDF for HMDB0033896 (Anacardic acid)

PDB for HMDB0033896 (Anacardic acid)

3D PDB for HMDB0033896 (Anacardic acid)

SMILES for HMDB0033896 (Anacardic acid)

INCHI for HMDB0033896 (Anacardic acid)

Structure for HMDB0033896 (Anacardic acid)

3D Structure for HMDB0033896 (Anacardic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra