NP-MRD: Showing NP-Card for Lilial (NP0333411)

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Record Information

Version

2.0

Created at

2024-06-17 18:49:10 UTC

Updated at

2024-09-03 04:22:21 UTC

NP-MRD ID

NP0333411

Natural Product DOI

https://doi.org/10.57994/2828

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lilial

Description

Lilial was first documented in 2015 (PMID: 25856710). Based on a literature review a significant number of articles have been published on Lilial (PMID: 29920544) (PMID: 37898679) (PMID: 36837654) (PMID: 36805910) (PMID: 36247979) (PMID: 33851853).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03012321242D          

 15 15  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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    0.8250    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
    0.7145   -0.4125    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
    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   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333411

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC1=CC=C(C=C1)C(C)(C)C)C=O

> <INCHI_IDENTIFIER>
InChI=1/C14H20O/c1-11(10-15)9-12-5-7-13(8-6-12)14(2,3)4/h5-8,10-11H,9H2,1-4H3

> <INCHI_KEY>
SDQFDHOLCGWZPU-UHFFFAOYNA-N

> <FORMULA>
C14H20O

> <MOLECULAR_WEIGHT>
204.313

> <EXACT_MASS>
204.151415264

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
24.70712708461132

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-tert-butylphenyl)-2-methylpropanal

> <JCHEM_LOGP>
3.984989067

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.95731879879034

> <JCHEM_PKA_STRONGEST_BASIC>
-7.021715808892605

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
64.28160000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
lilial

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 01-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAR-23         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.206  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    2   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₀O

Average Mass

204.3130 Da

Monoisotopic Mass

204.15142 Da

IUPAC Name

3-(4-tert-butylphenyl)-2-methylpropanal

Traditional Name

lilial

CAS Registry Number

Not Available

SMILES

CC(CC1=CC=C(C=C1)C(C)(C)C)C=O

InChI Identifier

InChI=1/C14H20O/c1-11(10-15)9-12-5-7-13(8-6-12)14(2,3)4/h5-8,10-11H,9H2,1-4H3

InChI Key

SDQFDHOLCGWZPU-UHFFFAOYNA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	3.98	ChemAxon
pKa (Strongest Acidic)	17.96	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	64.28 m³·mol⁻¹	ChemAxon
Polarizability	24.71 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lilial

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zeng F, Xu P, Tan K, Zarbin PHG, Leal WS: Methyl dihydrojasmonate and lilial are the constituents with an "off-label" insect repellence in perfumes. PLoS One. 2018 Jun 19;13(6):e0199386. doi: 10.1371/journal.pone.0199386. eCollection 2018. [PubMed:29920544 ]
Jablonska E, Michal Z, Krizkovska B, Strnad O, Tran VN, Zalmanova T, Petr J, Lipov J, Viktorova J: Toxicological investigation of lilial. Sci Rep. 2023 Oct 28;13(1):18536. doi: 10.1038/s41598-023-45598-y. [PubMed:37898679 ]
Lowry TW, Kusi-Appiah AE, Fadool DA, Lenhert S: Odor Discrimination by Lipid Membranes. Membranes (Basel). 2023 Jan 24;13(2):151. doi: 10.3390/membranes13020151. [PubMed:36837654 ]
Nakayama K, Zifle A, Fritz S, Fuchs A, Sakaguchi H, Miyazawa M: Incorporating integrated testing strategy (ITSv1) defined approach into read-across (RAx) in predicting skin sensitization potency: ITSv1-based RAx. Regul Toxicol Pharmacol. 2023 Mar;139:105358. doi: 10.1016/j.yrtph.2023.105358. Epub 2023 Feb 16. [PubMed:36805910 ]
Palagyi A, Jindrich J, Dian J, Fourmentin S: Cyclodextrin-based Schiff base pro-fragrances: Synthesis and release studies. Beilstein J Org Chem. 2022 Sep 28;18:1346-1354. doi: 10.3762/bjoc.18.140. eCollection 2022. [PubMed:36247979 ]
Tahir U, Hussam A, Roy P, Hashmi I: Noncovalent Association and Partitioning of Some Perfume Components at Infinite Dilution with Myelin Basic Protein Pseudophase in Normal Saline. Langmuir. 2021 Apr 27;37(16):4793-4801. doi: 10.1021/acs.langmuir.0c03475. Epub 2021 Apr 14. [PubMed:33851853 ]
Scherer M, Petreanu W, Weber T, Scherer G, Pluym N, Kolossa-Gehring M: Human biomonitoring in urine samples from the Environmental Specimen Bank reveals a decreasing trend over time in the exposure to the fragrance chemical lysmeral from 2000 to 2018. Chemosphere. 2021 Feb;265:128955. doi: 10.1016/j.chemosphere.2020.128955. Epub 2020 Nov 12. [PubMed:33220982 ]
Murawski A, Fiedler N, Schmied-Tobies MIH, Rucic E, Schwedler G, Stoeckelhuber M, Scherer G, Pluym N, Scherer M, Kolossa-Gehring M: Metabolites of the fragrance 2-(4-tert-butylbenzyl)propionaldehyde (lysmeral) in urine of children and adolescents in Germany - Human biomonitoring results of the German Environmental Survey 2014-2017 (GerES V). Int J Hyg Environ Health. 2020 Aug;229:113594. doi: 10.1016/j.ijheh.2020.113594. Epub 2020 Aug 5. [PubMed:32763837 ]
Armanino N, Charpentier J, Flachsmann F, Goeke A, Liniger M, Kraft P: What's Hot, What's Not: The Trends of the Past 20 Years in the Chemistry of Odorants. Angew Chem Int Ed Engl. 2020 Sep 14;59(38):16310-16344. doi: 10.1002/anie.202005719. Epub 2020 Jul 20. [PubMed:32453472 ]
Geppert M, Schwarz A, Stangassinger LM, Wenger S, Wienerroither LM, Ess S, Duschl A, Himly M: Interactions of TiO(2) Nanoparticles with Ingredients from Modern Lifestyle Products and Their Effects on Human Skin Cells. Chem Res Toxicol. 2020 May 18;33(5):1215-1225. doi: 10.1021/acs.chemrestox.9b00428. Epub 2020 Mar 5. [PubMed:32088960 ]
Ibrahim ALshaer F, Fuad ALBaharna D, Ahmed HO, Ghiyath Anas M, Mohammed ALJassmi J: Qualitative Analysis of Air Freshener Spray. J Environ Public Health. 2019 Nov 5;2019:9316707. doi: 10.1155/2019/9316707. eCollection 2019. [PubMed:31781257 ]
Soo Lim D, Min Choi S, Kim KB, Yoon K, Kacew S, Sik Kim H, Lee BM: Determination of fragrance allergens and their dermal sensitization quantitative risk assessment (QRA) in 107 spray perfumes. J Toxicol Environ Health A. 2018;81(22):1173-1185. doi: 10.1080/15287394.2018.1543232. Epub 2018 Nov 12. [PubMed:30415634 ]
Avonto C, Wang YH, Chittiboyina AG, Vukmanovic S, Khan IA: In chemico assessment of potential sensitizers: Stability and direct peptide reactivity of 24 fragrance ingredients. J Appl Toxicol. 2019 Feb;39(2):398-408. doi: 10.1002/jat.3732. Epub 2018 Oct 16. [PubMed:30325045 ]
Wolf S, Gelis L, Dorrich S, Hatt H, Kraft P: Evidence for a shape-based recognition of odorants in vivo in the human nose from an analysis of the molecular mechanism of lily-of-the-valley odorants detection in the Lilial and Bourgeonal family using the C/Si/Ge/Sn switch strategy. PLoS One. 2017 Aug 1;12(8):e0182147. doi: 10.1371/journal.pone.0182147. eCollection 2017. [PubMed:28763484 ]
Scherer M, Koch HM, Schutze A, Pluym N, Krnac D, Gilch G, Leibold E, Scherer G: Human metabolism and excretion kinetics of the fragrance lysmeral after a single oral dosage. Int J Hyg Environ Health. 2017 Mar;220(2 Pt A):123-129. doi: 10.1016/j.ijheh.2016.09.005. Epub 2016 Sep 12. [PubMed:27633268 ]
Busko M, Stuper K, Jelen H, Goral T, Chmielewski J, Tyrakowska B, Perkowski J: Comparison of Volatiles Profile and Contents of Trichothecenes Group B, Ergosterol, and ATP of Bread Wheat, Durum Wheat, and Triticale Grain Naturally Contaminated by Mycobiota. Front Plant Sci. 2016 Aug 22;7:1243. doi: 10.3389/fpls.2016.01243. eCollection 2016. [PubMed:27597856 ]
Pluym N, Krnac D, Gilch G, Scherer M, Leibold E, Scherer G: A liquid chromatography-tandem mass spectrometry (LC-MS/MS) method for the human biomonitoring of non-occupational exposure to the fragrance 2-(4-tert-butylbenzyl)propionaldehyde (lysmeral). Anal Bioanal Chem. 2016 Aug;408(21):5873-5882. doi: 10.1007/s00216-016-9702-x. Epub 2016 Jul 1. [PubMed:27370687 ]
Landum MC, Felix Mdo R, Alho J, Garcia R, Cabrita MJ, Rei F, Varanda CM: Antagonistic activity of fungi of Olea europaea L. against Colletotrichum acutatum. Microbiol Res. 2016 Feb;183:100-8. doi: 10.1016/j.micres.2015.12.001. Epub 2015 Dec 12. [PubMed:26805623 ]
Esmaeili A, Afshari S, Esmaeili D: Formation of harmful compounds in biotransformation of lilial by microorganisms isolated from human skin. Pharm Biol. 2015;53(12):1768-73. doi: 10.3109/13880209.2015.1005755. Epub 2015 Apr 9. [PubMed:25856710 ]

Showing NP-Card for Lilial (NP0333411)

MOL for NP0333411 (Lilial)

3D MOL for NP0333411 (Lilial)

3D SDF for NP0333411 (Lilial)

3D-SDF for NP0333411 (Lilial)

PDB for NP0333411 (Lilial)

3D PDB for NP0333411 (Lilial)

SMILES for NP0333411 (Lilial)

INCHI for NP0333411 (Lilial)

Structure for NP0333411 (Lilial)

3D Structure for NP0333411 (Lilial)