NP-MRD: Showing NP-Card for 24-Hydroxycholesterol (NP0086776)

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Record Information

Version

2.0

Created at

2022-05-11 16:30:40 UTC

Updated at

2022-05-11 16:30:40 UTC

NP-MRD ID

NP0086776

Secondary Accession Numbers

None

Natural Product Identification

Common Name

24-Hydroxycholesterol

Description

24-Hydroxycholesterol, also known as cholest-5-ene-3,24-diol or cerebrosterol, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Thus, 24-hydroxycholesterol is considered to be a sterol lipid molecule. 24-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, 24-hydroxycholesterol participates in a number of enzymatic reactions. In particular, 24-hydroxycholesterol can be biosynthesized from cholesterol; which is mediated by the enzyme cholesterol 24-hydroxylase. In addition, 24-hydroxycholesterol can be converted into (24R)-cholest-5-ene-3-β,7-α,24-triol through the action of the enzyme 24-hydroxycholesterol 7-alpha-hydroxylase. In humans, 24-hydroxycholesterol is involved in bile acid biosynthesis. 24-Hydroxycholesterol, with regard to humans, has been found to be associated with several diseases such as mild cognitive impairment, neuroborreliosis, subarachnoid hemorrhage, and meningitis; 24-hydroxycholesterol has also been linked to the inborn metabolic disorder hypercholesterolemia. 24-Hydroxycholesterol is found in Homo sapiens. 24-Hydroxycholesterol was first documented in 2003 (PMID: 14574622). A 24-hydroxycholesterol that has S configuration at position 24 (PMID: 15061359).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 02231219072D          

 33 36  0  0  1  0            999 V2000
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   12.8516  -12.8095    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5660  -13.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2805  -12.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2805  -11.9845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5660  -11.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 20 30  1  6  0  0  0
 31 27  1  0  0  0  0
 32 31  1  0  0  0  0
 33 31  1  0  0  0  0
M  END

     RDKit          3D

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M  END

  Mrv0541 02231219072D          

 33 36  0  0  1  0            999 V2000
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 12 19  1  1  0  0  0
 17 20  1  0  0  0  0
 10 21  1  6  0  0  0
  5 22  1  1  0  0  0
  9 23  1  1  0  0  0
 11 24  1  6  0  0  0
 25 20  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 27 28  1  6  0  0  0
 17 29  1  6  0  0  0
 20 30  1  6  0  0  0
 31 27  1  0  0  0  0
 32 31  1  0  0  0  0
 33 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086776

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
IOWMKBFJCNLRTC-XWXSNNQWSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.6529

> <EXACT_MASS>
402.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
51.13561923234171

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

> <ALOGPS_LOGP>
5.70

> <JCHEM_LOGP>
5.804124233666668

> <ALOGPS_LOGS>
-6.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.7789746459014

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9525922058984736

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
122.20899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.03e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
24(S)-hydroxycholesterol

> <JCHEM_VEBER_RULE>
0

$$$$

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      23.990 -22.371   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.990 -23.911   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.323 -24.681   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.657 -23.911   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.657 -22.371   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.323 -21.601   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.991 -24.681   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.324 -23.911   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.324 -22.371   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.991 -21.601   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.658 -21.601   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      30.658 -20.061   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.324 -19.291   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.991 -20.061   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.123 -22.077   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      33.028 -20.831   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      32.123 -19.585   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      22.656 -24.681   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      30.819 -18.529   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.599 -18.120   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      27.991 -23.141   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      26.657 -20.831   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      29.324 -20.831   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      30.819 -23.132   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0      34.105 -17.800   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      34.581 -16.336   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      36.087 -16.015   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      36.563 -14.551   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0      33.546 -19.250   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0      31.568 -16.976   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      37.118 -17.160   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      36.642 -18.624   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      38.624 -16.840   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   22                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   23                                             
CONECT   10    9    5   14   21                                             
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   20   29                                             
CONECT   18    2                                                            
CONECT   19   12                                                            
CONECT   20   17   25   30                                                  
CONECT   21   10                                                            
CONECT   22    5                                                            
CONECT   23    9                                                            
CONECT   24   11                                                            
CONECT   25   20   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27                                                            
CONECT   29   17                                                            
CONECT   30   20                                                            
CONECT   31   27   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(24S)-Hydroxycholesterol	ChEBI
24S-Hydroxy-cholesterol	ChEBI
Cerebrosterol	ChEBI
Cholest-5-en-3beta,24S-diol	ChEBI
Cholest-5-ene-3,24-diol	ChEBI
(24S)-24-Hydroxycholesterol	Kegg
(24S)-Cholest-5-ene-3beta,24-diol	Kegg
Cholest-5-en-3b,24S-diol	Generator
Cholest-5-en-3β,24S-diol	Generator
(24S)-Cholest-5-ene-3b,24-diol	Generator
(24S)-Cholest-5-ene-3β,24-diol	Generator
24(S)-Hydroxycholesterol	HMDB
24S-Cholest-5-ene-3b,24-diol	HMDB
24S-Hydroxycholesterol	HMDB
Cerebrosterin	HMDB
Cholest-5-ene-3b,24b-diol	HMDB

Chemical Formula

C₂₇H₄₆O₂

Average Mass

402.6529 Da

Monoisotopic Mass

402.34978 Da

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

Traditional Name

24(S)-hydroxycholesterol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1

InChI Key

IOWMKBFJCNLRTC-XWXSNNQWSA-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
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
Homo sapiens	LOTUS Database	35616633
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 dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

24-hydroxysteroid
Dihydroxy bile acid, alcohol, or derivatives
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

oxysterol (CHEBI:34310 )
24-hydroxycholesterol (CHEBI:34310 )
Cholesterol and derivatives (LMST01010019 )

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	5.7	ALOGPS
logP	5.8	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-0.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.21 m³·mol⁻¹	ChemAxon
Polarizability	51.14 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001419

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022611

KNApSAcK ID

Not Available

Chemspider ID

108790

KEGG Compound ID

C13550

BioCyc ID

Not Available

BiGG ID

2197434

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

121948

PDB ID

Not Available

ChEBI ID

34310

Good Scents ID

Not Available

References

General References

Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. doi: 10.1515/CCLM.2004.034. [PubMed:15061359 ]
Lutjohann D, von Bergmann K: 24S-hydroxycholesterol: a marker of brain cholesterol metabolism. Pharmacopsychiatry. 2003 Sep;36 Suppl 2:S102-6. doi: 10.1055/s-2003-43053. [PubMed:14574622 ]

Showing NP-Card for 24-Hydroxycholesterol (NP0086776)

MOL for NP0086776 (24-Hydroxycholesterol)

3D MOL for NP0086776 (24-Hydroxycholesterol)

3D SDF for NP0086776 (24-Hydroxycholesterol)

3D-SDF for NP0086776 (24-Hydroxycholesterol)

PDB for NP0086776 (24-Hydroxycholesterol)

3D PDB for NP0086776 (24-Hydroxycholesterol)

SMILES for NP0086776 (24-Hydroxycholesterol)

INCHI for NP0086776 (24-Hydroxycholesterol)

Structure for NP0086776 (24-Hydroxycholesterol)

3D Structure for NP0086776 (24-Hydroxycholesterol)