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Showing metabocard for 1-Naphthaleneacetic acid (HMDB0032708)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:19 UTC
Update Date2023-02-21 17:22:35 UTC
HMDB IDHMDB0032708
Secondary Accession Numbers
  • HMDB32708
Metabolite Identification
Common Name1-Naphthaleneacetic acid
DescriptionPlant growth regulator. 1-Naphthaleneacetic acid is used for control of preharvest fruit drop, flower induction and fruit thinning in various crops such as apples, potatoes, olives and citrus fruits.1-Naphthaleneacetic acid (NAA) is a plant hormone in the auxin family. It is a rooting agent and used for the vegetative propagation of plants from stem and leaf cutting. It is also used for plant tissue culture. NAA does not occur naturally. Under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA), products containing NAA require registration with the Environmental Protection Agency (EPA) as pesticides. (Wikipedia
Structure
Data?1677000155
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032708 (1-Naphthaleneacetic acid)

NLA
  Mrv0541 02231215422D          

 14 15  0  0  0  0            999 V2000
    0.3236    0.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909   -0.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054    0.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054    0.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909    1.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3236    0.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380    1.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7525    0.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7525    0.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380   -0.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909   -1.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054   -1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054   -2.4508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8198   -1.2133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  2 11  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
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3D MOL for HMDB0032708 (1-Naphthaleneacetic acid)

HMDB0032708
     RDKit          3D
1-Naphthaleneacetic acid
 24 25  0  0  0  0  0  0  0  0999 V2000
    1.6741   -0.0827   -2.2672 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4369   -0.4267   -1.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294   -1.0970   -1.5866 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1019   -0.1345    0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8307    0.5708    0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8174    1.9352    0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3879    2.5840    0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5806    1.8876    0.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6096    0.5265    0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7828   -0.1808    0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -1.5262    0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5412   -2.1450   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3626   -1.4775   -0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3689   -0.1104    0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792   -1.3857   -0.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2073   -1.0286    0.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9165    0.5539    0.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691    2.4456    0.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    3.6464    0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5385    2.3716    0.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7118    0.3288    0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7003   -2.1156    0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5098   -3.2060   -0.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6113   -1.9336   -0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  5  1  0
 14  9  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 13 24  1  0
M  END
Download

3D SDF for HMDB0032708 (1-Naphthaleneacetic acid)

NLA
  Mrv0541 02231215422D          

 14 15  0  0  0  0            999 V2000
    0.3236    0.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909   -0.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054    0.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054    0.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909    1.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3236    0.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380    1.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7525    0.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7525    0.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380   -0.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909   -1.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054   -1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054   -2.4508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8198   -1.2133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  2 11  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032708

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC1=C2C=CC=CC2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O2/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H,13,14)

> <INCHI_KEY>
PRPINYUDVPFIRX-UHFFFAOYSA-N

> <FORMULA>
C12H10O2

> <MOLECULAR_WEIGHT>
186.2066

> <EXACT_MASS>
186.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.41780433874981

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(naphthalen-1-yl)acetic acid

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
2.600470862

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.748363545036556

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
53.81580000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
plucker

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0032708 (1-Naphthaleneacetic acid)

HMDB0032708
     RDKit          3D
1-Naphthaleneacetic acid
 24 25  0  0  0  0  0  0  0  0999 V2000
    1.6741   -0.0827   -2.2672 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4369   -0.4267   -1.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294   -1.0970   -1.5866 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1019   -0.1345    0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8307    0.5708    0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8174    1.9352    0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3879    2.5840    0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5806    1.8876    0.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6096    0.5265    0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7828   -0.1808    0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -1.5262    0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5412   -2.1450   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3626   -1.4775   -0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3689   -0.1104    0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792   -1.3857   -0.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2073   -1.0286    0.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9165    0.5539    0.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691    2.4456    0.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    3.6464    0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5385    2.3716    0.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7118    0.3288    0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7003   -2.1156    0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5098   -3.2060   -0.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6113   -1.9336   -0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  5  1  0
 14  9  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
 13 24  1  0
M  END
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PDB for HMDB0032708 (1-Naphthaleneacetic acid)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: NLA                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.604   0.045   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.730  -0.725   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.063   0.045   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.063   1.585   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.730   2.355   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.604   1.585   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.938   2.355   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.271   1.585   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.271   0.045   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.938  -0.725   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.730  -2.265   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.063  -3.035   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.063  -4.575   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -3.397  -2.265   0.000  0.00  0.00           O+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    1    9                                                       
CONECT   11    2   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for HMDB0032708 (1-Naphthaleneacetic acid)

COMPND    HMDB0032708
HETATM    1  O1  UNL     1       1.674  -0.083  -2.267  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.437  -0.427  -1.340  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.629  -1.097  -1.587  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.102  -0.134   0.076  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.831   0.571   0.261  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.817   1.935   0.496  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.388   2.584   0.657  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.581   1.888   0.585  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.610   0.527   0.352  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.783  -0.181   0.285  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.767  -1.526   0.061  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.541  -2.145  -0.095  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.363  -1.478  -0.036  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.369  -0.110   0.192  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.279  -1.386  -0.889  1.00  0.00           H  
HETATM   16  H2  UNL     1       2.207  -1.029   0.726  1.00  0.00           H  
HETATM   17  H3  UNL     1       2.917   0.554   0.444  1.00  0.00           H  
HETATM   18  H4  UNL     1       1.769   2.446   0.544  1.00  0.00           H  
HETATM   19  H5  UNL     1      -0.413   3.646   0.839  1.00  0.00           H  
HETATM   20  H6  UNL     1      -2.538   2.372   0.708  1.00  0.00           H  
HETATM   21  H7  UNL     1      -3.712   0.329   0.409  1.00  0.00           H  
HETATM   22  H8  UNL     1      -3.700  -2.116   0.001  1.00  0.00           H  
HETATM   23  H9  UNL     1      -1.510  -3.206  -0.270  1.00  0.00           H  
HETATM   24  H10 UNL     1       0.611  -1.934  -0.152  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5   16   17
CONECT    5    6    6   14
CONECT    6    7   18
CONECT    7    8    8   19
CONECT    8    9   20
CONECT    9   10   10   14
CONECT   10   11   21
CONECT   11   12   12   22
CONECT   12   13   23
CONECT   13   14   14   24
END
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SMILES for HMDB0032708 (1-Naphthaleneacetic acid)

OC(=O)CC1=C2C=CC=CC2=CC=C1
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INCHI for HMDB0032708 (1-Naphthaleneacetic acid)

InChI=1S/C12H10O2/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H,13,14)
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Synonyms
Chemical FormulaC12H10O2
Average Molecular Weight186.2066
Monoisotopic Molecular Weight186.068079564
IUPAC Name2-(naphthalen-1-yl)acetic acid
Traditional Nameplucker
CAS Registry Number86-87-3
SMILES
OC(=O)CC1=C2C=CC=CC2=CC=C1
InChI Identifier
InChI=1S/C12H10O2/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H,13,14)
InChI KeyPRPINYUDVPFIRX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point134.5 - 135.5 °CNot Available
Boiling Point373.20 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.42 mg/mL at 20 °CNot Available
LogP2.24Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01750
Phenol Explorer Compound IDNot Available
FooDB IDFDB010669
KNApSAcK IDC00020743
Chemspider ID6601
KEGG Compound IDC13014
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1-Naphthaleneacetic_acid
METLIN IDNot Available
PubChem Compound6862
PDB IDNLA
ChEBI ID32918
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1155701
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .