NP-MRD: Showing NP-Card for 24-α-methylcholesterol (NP0214880)

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Record Information

Version

2.0

Created at

2022-09-05 14:18:11 UTC

Updated at

2022-09-05 14:18:11 UTC

NP-MRD ID

NP0214880

Secondary Accession Numbers

None

Natural Product Identification

Common Name

24-α-methylcholesterol

Description

24-Methylcholesterol, also known as campesterol, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. 24-α-methylcholesterol is found in Aureoumbra lagunensis, Bugula neritina, Cyclotella cryptica, Dictyuchus monosporus, Kalanchoe petitiana, Magallana gigas, Nymphaea caerulea, Panax ginseng, Paramphistomum epiclitum, Pneumocystis carinii, Chrysotila lamellosa, Sinularia brassica, Tamarix gallica, Thalassiosira eccentrica, Trigonella foenum-graecum, Ulva rigida, Verongula gigantea, Wrightia tinctoria and Zea mays. 24-α-methylcholesterol was first documented in 2008 (PMID: 17909855). Based on a literature review a small amount of articles have been published on 24-Methylcholesterol (PMID: 34585632) (PMID: 22239944) (PMID: 22702206) (PMID: 26872973).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052216182D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052216182D          

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M  END
> <DATABASE_ID>
NP0214880

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(C)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

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19?,20-,22+,23+,24-,25+,26+,27+,28-/m1/s1

> <INCHI_KEY>
SGNBVLSWZMBQTH-QGOUJLTDSA-N

> <FORMULA>
C28H48O

> <MOLECULAR_WEIGHT>
400.691

> <EXACT_MASS>
400.370516166

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
52.24676231673972

> <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)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

> <JCHEM_LOGP>
7.399908127000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <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>
125.16509999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-5,6-dimethylheptan-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                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      13.059  -3.899   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.393  -4.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.393  -6.209   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.726  -3.899   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.726  -2.359   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.060  -4.669   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.394  -3.899   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.728  -4.669   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.728  -6.209   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.061  -3.899   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.222  -2.367   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.729  -2.047   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.499  -3.381   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.005  -3.701   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.035  -2.556   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.542  -2.877   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.018  -4.341   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.524  -4.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.000  -6.126   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      31.506  -6.446   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      28.969  -7.271   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.463  -6.950   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.987  -5.486   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.957  -6.630   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      25.481  -5.166   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.450  -6.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.944  -5.990   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.468  -4.525   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.324  -5.556   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   14   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   13   10   29                                             
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
22,23-Dihydrobrassicasterol	MeSH
24 alpha-Methylcholest-5-en-3 beta-ol	MeSH
Campesterol	MeSH
Campesterol, (3beta)-isomer	MeSH
Campesterol, (3beta,24xi)-isomer	MeSH
Ergost-5-en-3 beta- ol, 24 epimer	MeSH

Chemical Formula

C₂₈H₄₈O

Average Mass

400.6910 Da

Monoisotopic Mass

400.37052 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)C(C)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

InChI Identifier

InChI=1S/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19?,20-,22+,23+,24-,25+,26+,27+,28-/m1/s1

InChI Key

SGNBVLSWZMBQTH-QGOUJLTDSA-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
Aureoumbra lagunensis	LOTUS Database	35616633
Bugula neritina	LOTUS Database	35616633
Cyclotella cryptica	LOTUS Database	35616633
Dictyuchus monosporus	LOTUS Database	35616633
Kalanchoe petitiana	LOTUS Database	35616633
Magallana gigas	LOTUS Database	35616633
Nymphaea caerulea	LOTUS Database	35616633
Panax ginseng	LOTUS Database	35616633
Paramphistomum epiclitum	LOTUS Database	35616633
Pneumocystis carinii	LOTUS Database	35616633
Ruttnera lamellosa	LOTUS Database	35616633
Sinularia brassica	LOTUS Database	35616633
Tamarix gallica	LOTUS Database	35616633
Thalassiosira eccentrica	LOTUS Database	35616633
Trigonella foenum-graecum	LOTUS Database	35616633
Ulva rigida	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 ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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
logP	7.4	ChemAxon
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	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	5	ChemAxon
Refractivity	125.17 m³·mol⁻¹	ChemAxon
Polarizability	52.25 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

19953328

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12358784

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zidan SAH, Abdelhamid RA, Alian A, Fouad MA, Matsunami K, Orabi MAA: Diterpenes and sterols from the Red Sea soft coral Sarcophyton trocheliophorum and their cytotoxicity and anti-leishmanial activities. J Asian Nat Prod Res. 2021 Sep 29:1-9. doi: 10.1080/10286020.2021.1979522. [PubMed:34585632 ]
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 ]
Tsukagoshi Y, Suzuki H, Seki H, Muranaka T, Ohyama K, Fujimoto Y: Ajuga Delta24-Sterol Reductase Catalyzes the Direct Reductive Conversion of 24-Methylenecholesterol to Campesterol. J Biol Chem. 2016 Apr 8;291(15):8189-98. doi: 10.1074/jbc.M115.703470. Epub 2016 Feb 12. [PubMed:26872973 ]
Arnqvist L, Persson M, Jonsson L, Dutta PC, Sitbon F: Overexpression of CYP710A1 and CYP710A4 in transgenic Arabidopsis plants increases the level of stigmasterol at the expense of sitosterol. Planta. 2008 Jan;227(2):309-17. doi: 10.1007/s00425-007-0618-8. Epub 2007 Oct 2. [PubMed:17909855 ]
LOTUS database [Link]

Showing NP-Card for 24-α-methylcholesterol (NP0214880)

MOL for NP0214880 (24-α-methylcholesterol)

3D MOL for NP0214880 (24-α-methylcholesterol)

3D SDF for NP0214880 (24-α-methylcholesterol)

3D-SDF for NP0214880 (24-α-methylcholesterol)

PDB for NP0214880 (24-α-methylcholesterol)

3D PDB for NP0214880 (24-α-methylcholesterol)

SMILES for NP0214880 (24-α-methylcholesterol)

INCHI for NP0214880 (24-α-methylcholesterol)

Structure for NP0214880 (24-α-methylcholesterol)

3D Structure for NP0214880 (24-α-methylcholesterol)