NP-MRD: Showing NP-Card for Lignoceryl alcohol (NP0046617)

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Record Information

Version

2.0

Created at

2022-03-17 20:08:49 UTC

Updated at

2024-09-03 04:16:49 UTC

NP-MRD ID

NP0046617

Natural Product DOI

https://doi.org/10.57994/0818

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lignoceryl alcohol

Description

Lignoceryl alcohol, also known as 1-tetracosanol or tetracosyl alcohol, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Thus, lignoceryl alcohol is considered to be a fatty alcohol lipid molecule. A very long-chain primary fatty alcohol that is tetracosane in which a hydrogen attached to one of the terminal carbons is replaced by a hydroxy group. Lignoceryl alcohol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Lignoceryl alcohol has been detected, but not quantified in, common hazelnuts. This could make lignoceryl alcohol a potential biomarker for the consumption of these foods. Lignoceryl alcohol is found in Arnebia hispidissima, Artemisia igniaria, Cinnamomum triplinerve, Convolvulus arvensis, Crataegus monogyna, Euphorbia falcata, Acca sellowiana, Gisekia pharnaceoides, Gynura japonica, Harpullia pendula, Hypericum perforatum, Larix gmelinii, Larix sibirica, Lolium perenne, Cryptolepis nigrescens, Petiveria alliacea, Pinus koraiensis , Pinus sibirica, Populus tremuloides, Prunus africana, Prunus laurocerasus, Persica vulgaris , Pycnandra acuminata, Sambucus nigra, Sebertia acuminata, Solanum tuberosum , Tanacetum longifolium and Triticum turgidum. Lignoceryl alcohol was first documented in 2010 (PMID: 19716291). It has been isolated from a variety of plants, including grape seeds, evening primrose (Oenothera biennis), pitaya fruits (Hylocereus polyrhizus and Hylocereus undatus), and the flowers of Arabian jasmine (Jasminum sambac) (PMID: 22417487) (PMID: 24239848) (PMID: 24386928).

Structure

MOL SDF PDB SMILES InChI

  Mrv1652309272007402D          

 25 24  0  0  0  0            999 V2000
10011.013510010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.729410011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.444110010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.159010011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.873810010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.588610011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.303310010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.018310011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.733110010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.447910011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.162510010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.877310011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.592310010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.298010011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.582410010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.868810011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.153210010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.437610011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.724210010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.008610011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.295010010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.579410011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.863810010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.150310011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.434710010.8176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  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
 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  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  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>
NP0046617

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCCCCCCCO

> <INCHI_IDENTIFIER>
InChI=1S/C24H50O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25/h25H,2-24H2,1H3

> <INCHI_KEY>
TYWMIZZBOVGFOV-UHFFFAOYSA-N

> <FORMULA>
C24H50O

> <MOLECULAR_WEIGHT>
354.6532

> <EXACT_MASS>
354.386166222

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.55977738952621

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
tetracosan-1-ol

> <ALOGPS_LOGP>
9.68

> <JCHEM_LOGP>
9.696695245999999

> <ALOGPS_LOGS>
-7.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.84394282199214

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9922594096606376

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
114.15489999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.54e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-tetracosanol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8687.2258686.859   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8688.5618687.628   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8689.8968686.859   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8691.2308687.628   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8692.5648686.859   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8693.8998687.628   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8695.2338686.859   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8696.5678687.628   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8697.9028686.859   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8699.2368687.628   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8700.5708686.859   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8701.9048687.628   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8703.2398686.859   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8685.8908687.628   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8684.5548686.859   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8683.2228687.628   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8681.8868686.859   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8680.5508687.628   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8679.2188686.859   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8677.8838687.628   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8676.5518686.859   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8675.2158687.628   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8673.8798686.859   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8672.5478687.628   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0    8671.2128686.859   0.000  0.00  0.00           O+0
CONECT    1    2   14                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    1   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   48    0
END

View in JSmol

Synonyms

Value	Source
1-Tetracosanol	ChEBI
Lignoceric alcohol	ChEBI
N-Tetracosanol	ChEBI
N-Tetracosanol-1	ChEBI
Tetracosanol	ChEBI
Tetracosyl alcohol	ChEBI
Lignoceryl alcohol	ChEBI
Lignocerol	PhytoBank

Chemical Formula

C₂₄H₅₀O

Average Mass

354.6532 Da

Monoisotopic Mass

354.38617 Da

IUPAC Name

tetracosan-1-ol

Traditional Name

1-tetracosanol

CAS Registry Number

506-51-4

SMILES

CCCCCCCCCCCCCCCCCCCCCCCCO

InChI Identifier

InChI=1S/C24H50O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25/h25H,2-24H2,1H3

InChI Key

TYWMIZZBOVGFOV-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-08-15	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-08-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arnebia hispidissima	LOTUS Database	35616633
Artemisia igniaria	LOTUS Database	35616633
Cinnamomum triplinerve	LOTUS Database	35616633
Convolvulus arvensis	LOTUS Database	35616633
Corylus avellana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Crataegus monogyna	LOTUS Database	35616633
Euphorbia falcata L.	LOTUS Database	35616633
Feijoa sellowiana	Plant	KNApSAcK
Gisekia pharnaceoides	LOTUS Database	35616633
Gynura japonica	LOTUS Database	35616633
Harpullia pendula	LOTUS Database	35616633
Hypericum perforatum	LOTUS Database	35616633
Larix gmelini	LOTUS Database	35616633
Larix sibirica	LOTUS Database	35616633
Lolium perenne	LOTUS Database	35616633
Periploca nigrescens	LOTUS Database	35616633
Petiveria alliacea	LOTUS Database	35616633
Pinus koraiensis	Plant	KNApSAcK
Pinus sibirica	Plant	KNApSAcK
Populus tremuloides	LOTUS Database	35616633
Prunus africana	LOTUS Database	35616633
Prunus laurocerasus	LOTUS Database	35616633
Prunus persica	-	KNApSAcK
Pycnandra acuminata	LOTUS Database	35616633
Sambucus nigra	LOTUS Database	35616633
Sebertia acuminata	Plant	KNApSAcK
Solanum tuberosum	Plant	KNApSAcK
Tanacetum longifolium	LOTUS Database	35616633
Triticum turgidum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain primary fatty alcohol (CHEBI:77413 )
fatty alcohol 24:0 (CHEBI:77413 )
Fatty alcohols (LMFA05000222 )
a long-chain alcohol (CPD-7874 )
a primary alcohol (CPD-7874 )
a fatty alcohol (CPD-7874 )

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	9.68	ALOGPS
logP	9.7	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	16.84	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	114.15 m³·mol⁻¹	ChemAxon
Polarizability	51.56 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0172388

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB005216

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-7874

BiGG ID

Not Available

Wikipedia Link

1-Tetracosanol

METLIN ID

Not Available

PubChem Compound

10472

PDB ID

Not Available

ChEBI ID

77413

Good Scents ID

Not Available

References

General References

Jung DM, Lee MJ, Yoon SH, Jung MY: A gas chromatography-tandem quadrupole mass spectrometric analysis of policosanols in commercial vegetable oils. J Food Sci. 2011 Aug;76(6):C891-9. doi: 10.1111/j.1750-3841.2011.02232.x. Epub 2011 Jun 21. [PubMed:22417487 ]
Dunford NT, Edwards J: Nutritional bioactive components of wheat straw as affected by genotype and environment. Bioresour Technol. 2010 Jan;101(1):422-5. doi: 10.1016/j.biortech.2009.08.009. Epub 2009 Aug 27. [PubMed:19716291 ]
Montserrat-de la Paz S, Garcia-Gimenez MD, Angel-Martin M, Perez-Camino MC, Fernandez Arche A: Long-chain fatty alcohols from evening primrose oil inhibit the inflammatory response in murine peritoneal macrophages. J Ethnopharmacol. 2014;151(1):131-6. doi: 10.1016/j.jep.2013.10.012. Epub 2013 Nov 15. [PubMed:24239848 ]
Luo H, Cai Y, Peng Z, Liu T, Yang S: Chemical composition and in vitro evaluation of the cytotoxic and antioxidant activities of supercritical carbon dioxide extracts of pitaya (dragon fruit) peel. Chem Cent J. 2014 Jan 3;8(1):1. doi: 10.1186/1752-153X-8-1. [PubMed:24386928 ]

Showing NP-Card for Lignoceryl alcohol (NP0046617)

MOL for NP0046617 (Lignoceryl alcohol)

3D MOL for NP0046617 (Lignoceryl alcohol)

3D SDF for NP0046617 (Lignoceryl alcohol)

3D-SDF for NP0046617 (Lignoceryl alcohol)

PDB for NP0046617 (Lignoceryl alcohol)

3D PDB for NP0046617 (Lignoceryl alcohol)

SMILES for NP0046617 (Lignoceryl alcohol)

INCHI for NP0046617 (Lignoceryl alcohol)

Structure for NP0046617 (Lignoceryl alcohol)

3D Structure for NP0046617 (Lignoceryl alcohol)