Np mrd loader

Showing NP-Card for Linalyl anthranilate (NP0338163)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2024-09-11 14:07:03 UTC
Updated at2024-09-11 14:07:04 UTC
NP-MRD IDNP0338163
Secondary Accession NumbersNone
Natural Product Identification
Common NameLinalyl anthranilate
Description Linalyl anthranilate was first documented in 2013 (PMID: 22989360). Based on a literature review a significant number of articles have been published on Linalyl anthranilate (PMID: 37990185) (PMID: 36552681) (PMID: 35930275) (PMID: 35039591) (PMID: 34012697) (PMID: 31238138).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0338163 (Linalyl anthranilate)


  Mrv2104 05262316392D          

 20 20  0  0  0  0            999 V2000
   -0.1914    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    3.1895    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  7  6  2  0  0  0  0
  9  8  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17  4  1  0  0  0  0
 17  5  1  0  0  0  0
 17 12  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  2  0  0  0  0
 20 16  1  0  0  0  0
 20 17  1  0  0  0  0
M  END
Download

3D MOL for NP0338163 (Linalyl anthranilate)

Download
3D SDF for NP0338163 (Linalyl anthranilate)

  Mrv2104 05262316392D          

 20 20  0  0  0  0            999 V2000
   -0.1914    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    3.1895    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  7  6  2  0  0  0  0
  9  8  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17  4  1  0  0  0  0
 17  5  1  0  0  0  0
 17 12  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  2  0  0  0  0
 20 16  1  0  0  0  0
 20 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338163

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC(C)(OC(=O)C1=CC=CC=C1N)C=C

> <INCHI_IDENTIFIER>
InChI=1/C17H23NO2/c1-5-17(4,12-8-9-13(2)3)20-16(19)14-10-6-7-11-15(14)18/h5-7,9-11H,1,8,12,18H2,2-4H3

> <INCHI_KEY>
WHIJSULEEDNKPD-UHFFFAOYNA-N

> <FORMULA>
C17H23NO2

> <MOLECULAR_WEIGHT>
273.376

> <EXACT_MASS>
273.172878985

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.05408786677551

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7-dimethylocta-1,6-dien-3-yl 2-aminobenzoate

> <JCHEM_LOGP>
4.963866347333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.37876963594049

> <JCHEM_PKA_STRONGEST_BASIC>
2.177430928633392

> <JCHEM_POLAR_SURFACE_AREA>
52.32000000000001

> <JCHEM_REFRACTIVITY>
84.72899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
linalyl anthranilate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0338163 (Linalyl anthranilate)
Download
PDB for NP0338163 (Linalyl anthranilate)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -0.357   5.954   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.437   3.286   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.897   5.954   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   13                                                            
CONECT    3   13                                                            
CONECT    4   17                                                            
CONECT    5    1   17                                                       
CONECT    6    7   10                                                       
CONECT    7    6   11                                                       
CONECT    8    9   12                                                       
CONECT    9    8   13                                                       
CONECT   10    6   14                                                       
CONECT   11    7   15                                                       
CONECT   12    8   17                                                       
CONECT   13    2    3    9                                                  
CONECT   14   10   15   16                                                  
CONECT   15   11   14   18                                                  
CONECT   16   14   19   20                                                  
CONECT   17    4    5   12   20                                             
CONECT   18   15                                                            
CONECT   19   16                                                            
CONECT   20   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

Download
3D PDB for NP0338163 (Linalyl anthranilate)
Download
SMILES for NP0338163 (Linalyl anthranilate)
CC(C)=CCCC(C)(OC(=O)C1=CC=CC=C1N)C=C
Download
INCHI for NP0338163 (Linalyl anthranilate)
InChI=1/C17H23NO2/c1-5-17(4,12-8-9-13(2)3)20-16(19)14-10-6-7-11-15(14)18/h5-7,9-11H,1,8,12,18H2,2-4H3
Download
View in JSmol
Synonyms
ValueSource
Linalyl anthranilic acidGenerator
Chemical FormulaC17H23NO2
Average Mass273.3760 Da
Monoisotopic Mass273.17288 Da
IUPAC Name3,7-dimethylocta-1,6-dien-3-yl 2-aminobenzoate
Traditional Namelinalyl anthranilate
CAS Registry NumberNot Available
SMILES
CC(C)=CCCC(C)(OC(=O)C1=CC=CC=C1N)C=C
InChI Identifier
InChI=1/C17H23NO2/c1-5-17(4,12-8-9-13(2)3)20-16(19)14-10-6-7-11-15(14)18/h5-7,9-11H,1,8,12,18H2,2-4H3
InChI KeyWHIJSULEEDNKPD-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
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
logP4.96ChemAxon
pKa (Strongest Acidic)19.38ChemAxon
pKa (Strongest Basic)2.18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity84.73 m³·mol⁻¹ChemAxon
Polarizability31.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Hussein BA, Karimi I, Yousofvand N: Chemo- and bio-informatics insight into anti-cholinesterase potentials of berries and leaves of Myrtus communis L., Myrtaceae: an in vitro/in silico study. BMC Complement Med Ther. 2023 Nov 21;23(1):421. doi: 10.1186/s12906-023-04241-z. [PubMed:37990185  ] 
  2. Jianu C, Rusu LC, Muntean I, Cocan I, Lukinich-Gruia AT, Golet I, Horhat D, Mioc M, Mioc A, Soica C, Bujanca G, Ilie AC, Muntean D: In Vitro and In Silico Evaluation of the Antimicrobial and Antioxidant Potential of Thymus pulegioides Essential Oil. Antioxidants (Basel). 2022 Dec 15;11(12):2472. doi: 10.3390/antiox11122472. [PubMed:36552681  ] 
  3. Liang JY, An Y, Hou ZB, Wang XD, Zhou F, Zhang J, Wang JL: Acute toxicity of Zanthoxylum bungeanum against two stored product insects and synergistic interactions between two major compounds limonene and linalool. J Environ Sci Health B. 2022;57(9):739-744. doi: 10.1080/03601234.2022.2107370.  Epub 2022 Aug 5. [PubMed:35930275  ] 
  4. Rashad YM, Abdel Razik ES, Darwish DB: Essential oil from Lavandula angustifolia elicits expression of three SbWRKY transcription factors and defense-related genes against sorghum damping-off. Sci Rep. 2022 Jan 17;12(1):857. doi: 10.1038/s41598-022-04903-x. [PubMed:35039591  ] 
  5. Yang SK, Yusoff K, Ajat M, Yap WS, Lim SE, Lai KS: Antimicrobial activity and mode of action of terpene linalyl anthranilate against carbapenemase-producing Klebsiella pneumoniae. J Pharm Anal. 2021 Apr;11(2):210-219. doi: 10.1016/j.jpha.2020.05.014. Epub 2020  Jun 6. [PubMed:34012697  ] 
  6. Api AM, Belsito D, Botelho D, Bruze M, Burton GA Jr, Buschmann J, Dagli ML, Date M, Dekant W, Deodhar C, Francis M, Fryer AD, Jones L, Joshi K, La Cava S, Lapczynski A, Liebler DC, O'Brien D, Patel A, Penning TM, Ritacco G, Romine J, Sadekar N, Salvito D, Schultz TW, Sipes IG, Sullivan G, Thakkar Y, Tokura Y, Tsang S: RIFM fragrance ingredient safety assessment, linalyl anthranilate, CAS Registry Number 7149-26-0. Food Chem Toxicol. 2019 Aug;130 Suppl 1:110610. doi: 10.1016/j.fct.2019.110610.  Epub 2019 Jun 22. [PubMed:31238138  ] 
  7. Navarrete A, Avila-Rosas N, Majin-Leon M, Balderas-Lopez JL, Alfaro-Romero A, Tavares-Carvalho JC: Mechanism of action of relaxant effect of Agastache mexicana ssp.mexicana essential oil in guinea-pig trachea smooth muscle. Pharm Biol. 2017 Dec;55(1):96-100. doi: 10.1080/13880209.2016.1230140. Epub 2016  Sep 22. [PubMed:27927103  ] 
  8. Zhang WJ, Guo SS, You CX, Geng ZF, Liang JY, Deng ZW, Wang CF, Du SS, Wang YY: Chemical Composition of Essential Oils from Zanthoxylum bungeanum Maxim. and Their Bioactivities against Lasioderma serricorne. J Oleo Sci. 2016 Oct 1;65(10):871-879. doi: 10.5650/jos.ess16038. Epub 2016 Sep  15. [PubMed:27628733  ] 
  9. Adaszynska M, Swarcewicz M, Dzieciol M, Dobrowolska A: Comparison of chemical composition and antibacterial activity of lavender varieties from Poland. Nat Prod Res. 2013;27(16):1497-501. doi: 10.1080/14786419.2012.724408. Epub 2012  Sep 19. [PubMed:22989360  ]