NP-MRD: Showing NP-Card for Cholest-5-ene (NP0086671)

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Record Information

Version

2.0

Created at

2022-05-11 16:27:43 UTC

Updated at

2022-05-11 16:27:44 UTC

NP-MRD ID

NP0086671

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cholest-5-ene

Description

Cholest-5-ene, also known as 5-cholestene, belongs to the class of organic compounds known as cholestane steroids. These are steroids with a structure containing the 27-carbon cholestane skeleton. Thus, cholest-5-ene is considered to be a sterol lipid molecule. Cholest-5-ene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In humans, cholest-5-ene is involved in the metabolic disorder called familial hypercholanemia (fhca). Cholest-5-ene is found in Apis cerana. Cholest-5-ene was first documented in 1974 (PMID: 4818028). Examples include fusidic acid, lanosterol, and stigmasterol (PMID: 7381336) (PMID: 11463788) (PMID: 6480716).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231218502D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02231218502D          

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M  END
> <DATABASE_ID>
NP0086671

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CCCC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H46/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h12,19-20,22-25H,6-11,13-18H2,1-5H3/t20-,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
DTGDZMYNKLTSKC-HKQCOZBKSA-N

> <FORMULA>
C27H46

> <MOLECULAR_WEIGHT>
370.6541

> <EXACT_MASS>
370.359951472

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
49.72856758456739

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene

> <ALOGPS_LOGP>
7.87

> <JCHEM_LOGP>
8.499607557666666

> <ALOGPS_LOGS>
-7.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
118.94699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.17e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cholest-5-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.189  -1.433   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.141  -0.662   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.525  -0.662   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.189  -2.988   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.141   0.887   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.606  -1.137   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.855  -1.433   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.525   0.887   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.525  -3.752   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.606   1.368   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.189   1.651   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.469   2.403   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.486   0.122   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.855  -2.988   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.191  -0.662   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.855   0.122   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.101   2.846   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.191  -3.752   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.521  -1.433   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.598   3.148   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.054   4.016   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.521  -2.988   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.607   1.998   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.091   2.281   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.080   1.105   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.547  -0.341   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.603   1.388   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      -1.189   0.122   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.141  -2.197   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.525  -2.217   0.000  0.00  0.00           H+0
CONECT    1    2    3    4   28                                             
CONECT    2    1    5    6   29                                             
CONECT    3    1    7    8   30                                             
CONECT    4    1    9                                                       
CONECT    5    2   10   11   12                                             
CONECT    6    2   13                                                       
CONECT    7    3   14   15   16                                             
CONECT    8    3   11                                                       
CONECT    9    4   14                                                       
CONECT   10    5   17   13                                                  
CONECT   11    5    8                                                       
CONECT   12    5                                                            
CONECT   13    6   10                                                       
CONECT   14    7   18    9                                                  
CONECT   15    7   19                                                       
CONECT   16    7                                                            
CONECT   17   10   20   21                                                  
CONECT   18   14   22                                                       
CONECT   19   15   22                                                       
CONECT   20   17   23                                                       
CONECT   21   17                                                            
CONECT   22   18   19                                                       
CONECT   23   20   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28    1                                                            
CONECT   29    2                                                            
CONECT   30    3                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
5-Cholestene	ChEBI
D5-Cholestene	HMDB
Cholest-5-ene	KEGG

Chemical Formula

C₂₇H₄₆

Average Mass

370.6541 Da

Monoisotopic Mass

370.35995 Da

IUPAC Name

(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene

Traditional Name

cholest-5-ene

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CCCC[C@]12C

InChI Identifier

InChI=1S/C27H46/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h12,19-20,22-25H,6-11,13-18H2,1-5H3/t20-,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

DTGDZMYNKLTSKC-HKQCOZBKSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Apis cerana	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholestane steroids. These are steroids with a structure containing the 27-carbon cholestane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholestane steroids

Alternative Parents

Substituents

Cholestane-skeleton
Delta-5-steroid
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cholestanoid (CHEBI:28810 )
Cholesterol and derivatives (LMST01010243 )

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	7.87	ALOGPS
logP	8.5	ChemAxon
logS	-7.5	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	118.95 m³·mol⁻¹	ChemAxon
Polarizability	49.73 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

HMDB0000941

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022329

KNApSAcK ID

Not Available

Chemspider ID

389543

KEGG Compound ID

C05416

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5889

PubChem Compound

440663

PDB ID

Not Available

ChEBI ID

28810

Good Scents ID

Not Available

References

General References

Waters JA: Photosensitized isomerization-hydration of 5-cholestene. Steroids. 1974 Feb;23(2):259-67. doi: 10.1016/0039-128x(74)90156-1. [PubMed:4818028 ]
Swell L, Gustafsson J, Schwartz CC, Halloran LG, Danielsson H, Vlahcevic ZR: An in vivo evaluation of the quantitative significance of several potential pathways to cholic and chenodeoxycholic acids from cholesterol in man. J Lipid Res. 1980 May;21(4):455-66. [PubMed:7381336 ]
Bjorkhem I, Andersson U, Ellis E, Alvelius G, Ellegard L, Diczfalusy U, Sjovall J, Einarsson C: From brain to bile. Evidence that conjugation and omega-hydroxylation are important for elimination of 24S-hydroxycholesterol (cerebrosterol) in humans. J Biol Chem. 2001 Oct 5;276(40):37004-10. doi: 10.1074/jbc.M103828200. Epub 2001 Jul 19. [PubMed:11463788 ]
Esfahani M, Scerbo L, Devlin TM: A requirement for cholesterol and its structural features for a human macrophage-like cell line. J Cell Biochem. 1984;25(2):87-97. doi: 10.1002/jcb.240250204. [PubMed:6480716 ]

Showing NP-Card for Cholest-5-ene (NP0086671)

MOL for NP0086671 (Cholest-5-ene)

3D MOL for NP0086671 (Cholest-5-ene)

3D SDF for NP0086671 (Cholest-5-ene)

3D-SDF for NP0086671 (Cholest-5-ene)

PDB for NP0086671 (Cholest-5-ene)

3D PDB for NP0086671 (Cholest-5-ene)

SMILES for NP0086671 (Cholest-5-ene)

INCHI for NP0086671 (Cholest-5-ene)

Structure for NP0086671 (Cholest-5-ene)

3D Structure for NP0086671 (Cholest-5-ene)