NP-MRD: Showing NP-Card for 27-Hydroxycholesterol (NP0086872)

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Record Information

Version

2.0

Created at

2022-05-11 16:33:22 UTC

Updated at

2022-05-11 16:33:22 UTC

NP-MRD ID

NP0086872

Secondary Accession Numbers

None

Natural Product Identification

Common Name

27-Hydroxycholesterol

Description

27-Hydroxycholesterol, also known as cholest-5-ene-3b,27-diol, 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, 27-hydroxycholesterol is considered to be a sterol lipid molecule. 27-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, 27-hydroxycholesterol participates in a number of enzymatic reactions. In particular, 27-hydroxycholesterol can be biosynthesized from cholesterol through the action of the enzyme 25-hydroxycholesterol 7-alpha-hydroxylase. In addition, 27-hydroxycholesterol can be converted into 7-a,27-dihydroxycholesterol through the action of the enzyme cholesterol 7-alpha-monooxygenase. In humans, 27-hydroxycholesterol is involved in the metabolic disorder called familial hypercholanemia (fhca). 27-Hydroxycholesterol is a potentially toxic compound. 27-Hydroxycholesterol was first documented in 1986 (PMID: 3795956). A 27-Hydroxycholesterol in which the 25-position has R-configuration (PMID: 14729854) (PMID: 11504730) (PMID: 10832098) (PMID: 12719428).

Structure

MOL 3D MOL SDF PDB SMILES InChI

            
  Mrv1652306041823012D          

 33 36  0  0  0  0            999 V2000
 9999.658210001.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5210 9999.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3797 9997.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2333 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9458 9999.9734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6582 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2333 9999.5594    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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 9999.730710001.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.160510001.0576    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
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 20  6  1  6  0  0  0
 19  1  1  1  0  0  0
 12 20  1  0  0  0  0
M  END

     RDKit          3D

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M  END

            
  Mrv1652306041823012D          

 33 36  0  0  0  0            999 V2000
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 23 22  1  0  0  0  0
 13 19  1  0  0  0  0
 20  6  1  6  0  0  0
 19  1  1  1  0  0  0
 12 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086872

> <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)CCC[C@@H](C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
FYHRJWMENCALJY-YSQMORBQSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.6529

> <EXACT_MASS>
402.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.56438165391161

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

> <ALOGPS_LOGP>
6.21

> <JCHEM_LOGP>
5.754164144

> <ALOGPS_LOGS>
-6.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.20428950550382

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.41832287471465

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2349407421574696

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
122.46819999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.11e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JUN-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-18         0                                  
HETATM    1  C   UNK     0    8666.0298668.943   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.0398666.617   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.0428662.754   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8663.3698664.313   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8664.6998666.617   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8666.0298664.313   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8663.3698665.844   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.0358665.074   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.0358663.534   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.3698662.764   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.7038663.534   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.7038665.074   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.6998668.169   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.3658667.398   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.7078665.841   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8659.3738665.071   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8659.3738663.531   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8660.7078662.761   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.0338667.398   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.0338665.859   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8667.4978665.383   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.4028666.629   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.4978667.875   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8667.4978669.415   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.8338670.181   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8670.1658669.415   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8671.4978670.181   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8672.8338669.415   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8674.1658670.181   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0    8675.5058669.415   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0    8672.8338667.875   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8666.1648670.181   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0    8668.8338668.641   0.000  0.00  0.00           H+0
CONECT    1   19                                                            
CONECT    2    8                                                            
CONECT    3   17                                                            
CONECT    4    7                                                            
CONECT    5   12                                                            
CONECT    6   20                                                            
CONECT    7    8   12   14    4                                             
CONECT    8    7    9   15    2                                             
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    7   11    5   20                                             
CONECT   13   14   19                                                       
CONECT   14   13    7                                                       
CONECT   15   16    8                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18    3                                                  
CONECT   18   17    9                                                       
CONECT   19   20   23   13    1                                             
CONECT   20   19   21    6   12                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   24   33   19   22                                             
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28                                                            
CONECT   32   24                                                            
CONECT   33   23                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(25R)-26-Hydroxycholesterol	ChEBI
5-Cholestene-3beta,27-diol	ChEBI
Cholest-5-ene-3beta,27-diol	ChEBI
5-Cholestene-3b,27-diol	Generator
5-Cholestene-3β,27-diol	Generator
Cholest-5-ene-3b,27-diol	Generator
Cholest-5-ene-3β,27-diol	Generator
(25R)-Cholest-5-ene-3b,26-diol	HMDB
(25R)-Cholest-5-ene-3beta,26-diol	HMDB
(3-beta)-Cholest-5-ene-3,26-diol	HMDB
(3b,25R)-Cholest-5-ene-3,26-diol	HMDB
(3beta,25R)-Cholest-5-ene-3,26,diol	HMDB
26-Hydroxycholesterol(25R)	HMDB
Cholest-(25R)-5-en-3beta,26-diol	HMDB
Cholest-5-ene-3-b,27-diol	HMDB
Cholest-5-ene-3-beta,26-diol	HMDB
Cholest-5-ene-3-beta,27-diol	HMDB
Cholest-5-ene-3beta,26-diol	HMDB
Cholest-5-ene-3 beta,27-diol	HMDB
5-Cholestene-3 beta,27-diol	HMDB
(25R)-Cholest-5-ene-3β,26-diol	HMDB
(3Β,25R)-cholest-5-ene-3,26-diol	HMDB
(3beta,25R)-Cholest-5-ene-3,26-diol	HMDB
Cholest-5-ene-3β,26-diol	HMDB
(3Β)-cholest-5-ene-3,26-diol	HMDB
(3beta)-Cholest-5-ene-3,26-diol	HMDB
26-Hydroxycholesterol	HMDB
(3 beta,25R)-Cholest-5-ene-3,26-diol	HMDB
26-Hydroxycholesterol, (25R)	HMDB
(25R)-Cholest-5-ene-3 beta,26-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,6R)-7-hydroxy-6-methylheptan-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,6R)-7-hydroxy-6-methylheptan-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

[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)CCC[C@@H](C)CO

InChI Identifier

InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

FYHRJWMENCALJY-YSQMORBQSA-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
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

26-hydroxysteroid
Dihydroxy bile acid, alcohol, or derivatives
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
Delta-5-steroid
Fatty alcohol
Fatty acyl
Cyclic alcohol
Secondary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

26-hydroxycholesterol (CHEBI:76591 )
Cholesterol and derivatives (LMST01010088 )

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	6.21	ALOGPS
logP	5.75	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	17.42	ChemAxon
pKa (Strongest Basic)	-1.2	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	6	ChemAxon
Refractivity	122.47 m³·mol⁻¹	ChemAxon
Polarizability	51.56 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0002103

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022846

KNApSAcK ID

Not Available

Chemspider ID

110495

KEGG Compound ID

C06340

BioCyc ID

Not Available

BiGG ID

48021

Wikipedia Link

27-Hydroxycholesterol

METLIN ID

6487

PubChem Compound

123976

PDB ID

Not Available

ChEBI ID

76591

Good Scents ID

Not Available

References

General References

Burkard I, Rentsch KM, von Eckardstein A: Determination of 24S- and 27-hydroxycholesterol in plasma by high-performance liquid chromatography-mass spectrometry. J Lipid Res. 2004 Apr;45(4):776-81. doi: 10.1194/jlr.D300036-JLR200. Epub 2004 Jan 16. [PubMed:14729854 ]
Fu X, Menke JG, Chen Y, Zhou G, MacNaul KL, Wright SD, Sparrow CP, Lund EG: 27-hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells. J Biol Chem. 2001 Oct 19;276(42):38378-87. doi: 10.1074/jbc.M105805200. Epub 2001 Aug 14. [PubMed:11504730 ]
Rajagopalon I, Kok E, Cohen BI, Javitt NB: 26-Hydroxycholesterol disulfate: metabolism and excretion in the normal neonate. J Steroid Biochem. 1986 Dec;25(6):991-4. doi: 10.1016/0022-4731(86)90334-1. [PubMed:3795956 ]
Li S, Pang J, Jackson EM, Wilson WK, Mott GE, Schroepfer GJ Jr: Kinetics and plasma concentrations of 26-hydroxycholesterol in baboons. Biochim Biophys Acta. 2000 May 31;1485(2-3):173-84. doi: 10.1016/s1388-1981(00)00058-5. [PubMed:10832098 ]
Frolov A, Zielinski SE, Crowley JR, Dudley-Rucker N, Schaffer JE, Ory DS: NPC1 and NPC2 regulate cellular cholesterol homeostasis through generation of low density lipoprotein cholesterol-derived oxysterols. J Biol Chem. 2003 Jul 11;278(28):25517-25. doi: 10.1074/jbc.M302588200. Epub 2003 Apr 28. [PubMed:12719428 ]

Showing NP-Card for 27-Hydroxycholesterol (NP0086872)

MOL for NP0086872 (27-Hydroxycholesterol)

3D MOL for NP0086872 (27-Hydroxycholesterol)

3D SDF for NP0086872 (27-Hydroxycholesterol)

3D-SDF for NP0086872 (27-Hydroxycholesterol)

PDB for NP0086872 (27-Hydroxycholesterol)

3D PDB for NP0086872 (27-Hydroxycholesterol)

SMILES for NP0086872 (27-Hydroxycholesterol)

INCHI for NP0086872 (27-Hydroxycholesterol)

Structure for NP0086872 (27-Hydroxycholesterol)

3D Structure for NP0086872 (27-Hydroxycholesterol)