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Showing NP-Card for 1-Naphthaleneacetic acid (NP0136988)

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Record Information
Version1.0
Created at2022-05-30 16:38:14 UTC
Updated at2022-05-30 16:38:15 UTC
NP-MRD IDNP0136988
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-Naphthaleneacetic acid
Description1-Naphthaleneacetic acid, also known as NAA or alpha-naphthylacetic acid, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. 1-Naphthaleneacetic acid is found in Carapichea ipecacuanha. It was first documented in 2014 (PMID: 24272685). 1-Naphthaleneacetic acid is a weakly acidic compound (based on its pKa) (PMID: 24690897).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0136988 (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
Download

3D MOL for NP0136988 (1-Naphthaleneacetic acid)

     RDKit          3D

 24 25  0  0  0  0  0  0  0  0999 V2000
    3.1593    0.7441    0.7951 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7869   -0.2808    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1467   -1.5176    0.6038 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9805   -0.1005   -1.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828    0.5812   -0.7099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5572    1.9611   -0.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6204    2.5556   -0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6696    1.8652    0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584    0.4852    0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6134   -0.2070    0.7840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5229   -1.5743    0.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3452   -2.1812    0.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803   -1.4819    0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3671   -0.1054   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8901   -1.7183    1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7434   -1.0262   -1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4880    0.5767   -1.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3912    2.5154   -1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586    3.6347   -0.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951    2.3304    0.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5430    0.2884    1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3449   -2.1283    1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2346   -3.2501    0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6274   -1.9664   -0.2352 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  1  0
  5 14  2  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  9 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
 13 24  1  0
 12 23  1  0
 11 22  1  0
 10 21  1  0
  8 20  1  0
  7 19  1  0
  6 18  1  0
M  END
Download

3D SDF for NP0136988 (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>
NP0136988

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
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3D-SDF for NP0136988 (1-Naphthaleneacetic acid)

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PDB for NP0136988 (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 NP0136988 (1-Naphthaleneacetic acid)
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SMILES for NP0136988 (1-Naphthaleneacetic acid)
OC(=O)CC1=C2C=CC=CC2=CC=C1
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INCHI for NP0136988 (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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View in JSmol
Synonyms
ValueSource
alpha-NAAChEBI
alpha-Naphthaleneacetic acidChEBI
NAAChEBI
NAPHTHALEN-1-yl-acetIC ACIDChEBI
Naphthalene-1-acetic acidChEBI
alpha-Naphthylacetic acidKegg
a-NAAGenerator
Α-naaGenerator
a-NaphthaleneacetateGenerator
a-Naphthaleneacetic acidGenerator
alpha-NaphthaleneacetateGenerator
Α-naphthaleneacetateGenerator
Α-naphthaleneacetic acidGenerator
NAPHTHALEN-1-yl-acetateGenerator
Naphthalene-1-acetateGenerator
a-NaphthylacetateGenerator
a-Naphthylacetic acidGenerator
alpha-NaphthylacetateGenerator
Α-naphthylacetateGenerator
Α-naphthylacetic acidGenerator
1-NaphthaleneacetateGenerator
(1-Naphthyl)acetic acid, bsi, isoHMDB
1-NAAHMDB
1-Naphthylacetic acidHMDB
2-(alpha-Naphthyl)ethanoic acidHMDB
Fruitone NHMDB
PhyomoneHMDB
PlanofixHMDB
Tre-holdHMDB
1-Naphthaleneacetic acid, ammonium saltHMDB
1-Naphthaleneacetic acid, potassium saltHMDB
1-Naphthaleneacetic acid, sodium saltHMDB
Galle-donauHMDB
1-NaphthylacetateHMDB
2-(1-Naphthyl)acetic acidHMDB
2-(Naphthalen-1-yl)acetic acidHMDB
Potassium 1-naphthaleneacetateHMDB
Sodium 1-naphthaleneacetateHMDB
1-Naphthaleneacetic acidChEBI
Chemical FormulaC12H10O2
Average Mass186.2066 Da
Monoisotopic Mass186.06808 Da
IUPAC Name2-(naphthalen-1-yl)acetic acid
Traditional Nameplucker
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cephaelis ipecacuanhaLOTUS Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.97ALOGPS
logP2.6ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity53.82 m³·mol⁻¹ChemAxon
Polarizability19.42 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032708  
DrugBank IDDB01750  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010669  
KNApSAcK IDNot Available
Chemspider ID6601  
KEGG Compound IDC13014  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1-Naphthaleneacetic_acid  
METLIN IDNot Available
PubChem Compound6862  
PDB IDNLA  
ChEBI ID32918  
Good Scents IDNot Available
References
General References
  1. Li Y, Gao Z, Piao C, Lu K, Wang Z, Cui ML: A stable and efficient Agrobacterium tumefaciens-mediated genetic transformation of the medicinal plant Digitalis purpurea L. Appl Biochem Biotechnol. 2014 Feb;172(4):1807-17. doi: 10.1007/s12010-013-0648-6. Epub 2013 Nov 24. [PubMed:24272685  ] 
  2. Turi CE, Axwik KE, Smith A, Jones AM, Saxena PK, Murch SJ: Galanthamine, an anticholinesterase drug, effects plant growth and development in Artemisia tridentate Nutt. via modulation of auxin and neutrotransmitter signaling. Plant Signal Behav. 2014;9(3):e28645. Epub 2014 Mar 31. [PubMed:24690897  ]