NP-MRD: Showing NP-Card for 24-α-ethylcholesterol (NP0300680)

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Record Information

Version

2.0

Created at

2022-09-10 13:12:52 UTC

Updated at

2022-09-10 13:12:52 UTC

NP-MRD ID

NP0300680

Secondary Accession Numbers

None

Natural Product Identification

Common Name

24-α-ethylcholesterol

Description

24-Ethylcholesterol, also known as beta-sitosterol or harzol, belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. 24-α-ethylcholesterol is found in Bugula neritina, Canistrocarpus cervicornis, Crambe crambe, Cribricellina cribraria, Cyclotella cryptica, Ulva linza, Kalanchoe marmorata, Nitellopsis obtusa, Panax ginseng, Paramphistomum epiclitum, Petrosia durissima, Pneumocystis carinii, Tamarix gallica, Thalassiosira eccentrica, Verongula gigantea, Wrightia tinctoria and Zea mays. 24-α-ethylcholesterol was first documented in 2003 (PMID: 12785514). Based on a literature review a significant number of articles have been published on 24-Ethylcholesterol (PMID: 16647727) (PMID: 31121891) (PMID: 28956835) (PMID: 26268617) (PMID: 22239944) (PMID: 22702206).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102215122D          

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M  END

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  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0300680

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21?,23+,24+,25-,26+,27+,28+,29-/m1/s1

> <INCHI_KEY>
KZJWDPNRJALLNS-OAIXMFQVSA-N

> <FORMULA>
C29H50O

> <MOLECULAR_WEIGHT>
414.718

> <EXACT_MASS>
414.38616623

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
54.079059694967874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

> <JCHEM_LOGP>
7.844476792000004

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972437702926293

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
129.76609999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      15.479  -0.353   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.939  -0.353   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.169  -1.687   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.629  -1.687   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.859  -3.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.319  -3.020   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.549  -4.354   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.549  -1.687   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.018  -1.526   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.697  -0.019   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.031   0.751   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.351   2.257   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.207   3.288   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.527   4.794   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.992   5.270   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.312   6.776   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.776   7.252   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.097   8.758   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.921   6.222   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.601   4.715   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.136   4.239   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.281   3.209   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.816   2.733   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.960   1.702   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.640   0.196   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.176  -0.280   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.206  -1.424   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.939  -3.020   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.479  -3.020   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.169  -4.354   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   26                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   12   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   11    8   27                                             
CONECT   27   26                                                            
CONECT   28    3   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
beta-Sitosterol	MeSH
24-Ethylcholest-5-en-3 beta-ol	MeSH
3beta-Sitosterol	MeSH
3beta-Stigmast-5-en-3-ol	MeSH
gamma-Sitosterol	MeSH
Harzol	MeSH
Clionasterol	MeSH
Sitosterol	MeSH
Sitosterol, (3beta)-isomer	MeSH
Sitosterol, (3beta,24xi)-isomer	MeSH
Sitosterol, 26-(14)C-labeled	MeSH

Chemical Formula

C₂₉H₅₀O

Average Mass

414.7180 Da

Monoisotopic Mass

414.38617 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

InChI Identifier

InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21?,23+,24+,25-,26+,27+,28+,29-/m1/s1

InChI Key

KZJWDPNRJALLNS-OAIXMFQVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bugula neritina	LOTUS Database	35616633
Canistrocarpus cervicornis	LOTUS Database	35616633
Crambe crambe	LOTUS Database	35616633
Cribricellina cribraria	LOTUS Database	35616633
Cyclotella cryptica	LOTUS Database	35616633
Enteromorpha linza	LOTUS Database	35616633
Kalanchoe marmorata	LOTUS Database	35616633
Nitellopsis obtusa	LOTUS Database	35616633
Panax ginseng	LOTUS Database	35616633
Paramphistomum epiclitum	LOTUS Database	35616633
Petrosia durissima	LOTUS Database	35616633
Pneumocystis carinii	LOTUS Database	35616633
Tamarix gallica	LOTUS Database	35616633
Thalassiosira eccentrica	LOTUS Database	35616633
Verongula gigantea	LOTUS Database	35616633
Wrightia tinctoria	LOTUS Database	35616633
Zea mays	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

C24-propyl-sterol-skeleton
Stigmastane-skeleton
Triterpenoid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00046574

Chemspider ID

7998858

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9823110

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Muchembled J, Sahraoui AL, Grandmougin-Ferjani A, Sancholle M: Changes in lipid composition of Blumeria graminis f.sp. tritici conidia produced on wheat leaves treated with heptanoyl salicylic acid. Phytochemistry. 2006 Jun;67(11):1104-9. doi: 10.1016/j.phytochem.2006.02.025. Epub 2006 May 2. [PubMed:16647727 ]
Seong SH, Nguyen DH, Wagle A, Woo MH, Jung HA, Choi JS: Experimental and Computational Study to Reveal the Potential of Non-Polar Constituents from Hizikia fusiformis as Dual Protein Tyrosine Phosphatase 1B and alpha-Glucosidase Inhibitors. Mar Drugs. 2019 May 22;17(5). pii: md17050302. doi: 10.3390/md17050302. [PubMed:31121891 ]
Li GL, Guo WJ, Wang GB, Wang RR, Hou YX, Liu K, Liu Y, Wang W: Sterols from the Green Alga Ulva australis. Mar Drugs. 2017 Sep 28;15(10):299. doi: 10.3390/md15100299. [PubMed:28956835 ]
Ulbricht CE: An Evidence-Based Systematic Review of Beta-Sitosterol, Sitosterol (22,23- dihydrostigmasterol, 24-ethylcholesterol) by the Natural Standard Research Collaboration. J Diet Suppl. 2016;13(1):35-92. Epub 2015 Aug 13. [PubMed:26268617 ]
Calonne M, Sahraoui AL, Campagnac E, Debiane D, Laruelle F, Grandmougin-Ferjani A, Fontaine J: Propiconazole inhibits the sterol 14alpha-demethylase in Glomus irregulare like in phytopathogenic fungi. Chemosphere. 2012 Apr;87(4):376-83. doi: 10.1016/j.chemosphere.2011.12.027. Epub 2012 Jan 10. [PubMed:22239944 ]
Calonne M, Fontaine J, Debiane D, Laruelle F, Grandmougin A, Lounes-Hadj Sahraoui A: Side effects of the sterol biosynthesis inhibitor fungicide, propiconazole, on a beneficial arbuscular mycorrhizal fungus. Commun Agric Appl Biol Sci. 2011;76(4):891-902. [PubMed:22702206 ]
Nash D, Leeming R, Clemow L, Hannah M, Halliwell D, Allen D: Quantitative determination of sterols and other alcohols in overland flow from grazing land and possible source materials. Water Res. 2005 Aug;39(13):2964-78. doi: 10.1016/j.watres.2005.04.063. [PubMed:15998530 ]
Radke M, Herrmann R: Aerosol-bound emissions of polycyclic aromatic hydrocarbons and sterols from aeration tanks of a municipal waste water treatment plant. Environ Sci Technol. 2003 May 15;37(10):2109-13. doi: 10.1021/es025926g. [PubMed:12785514 ]
LOTUS database [Link]

Showing NP-Card for 24-α-ethylcholesterol (NP0300680)

MOL for NP0300680 (24-α-ethylcholesterol)

3D MOL for NP0300680 (24-α-ethylcholesterol)

3D SDF for NP0300680 (24-α-ethylcholesterol)

3D-SDF for NP0300680 (24-α-ethylcholesterol)

PDB for NP0300680 (24-α-ethylcholesterol)

3D PDB for NP0300680 (24-α-ethylcholesterol)

SMILES for NP0300680 (24-α-ethylcholesterol)

INCHI for NP0300680 (24-α-ethylcholesterol)

Structure for NP0300680 (24-α-ethylcholesterol)

3D Structure for NP0300680 (24-α-ethylcholesterol)