NP-MRD: Showing NP-Card for 26-hydroxycholesterol (NP0286761)

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Record Information

Version

2.0

Created at

2022-09-09 15:29:26 UTC

Updated at

2022-09-09 15:29:27 UTC

NP-MRD ID

NP0286761

Secondary Accession Numbers

None

Natural Product Identification

Common Name

26-hydroxycholesterol

Description

26-Hydroxycholesterol, also known as cholest-5-ene-3b,26-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, 26-hydroxycholesterol is considered to be a sterol lipid molecule. An oxysterol that is cholesterol substituted at position 26 by a hydroxy group. 26-hydroxycholesterol is found in Homo sapiens. 26-hydroxycholesterol was first documented in 2010 (PMID: 19761868). 26-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306041822072D          

 33 36  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652306041822072D          

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M  END
> <DATABASE_ID>
NP0286761

> <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)CCCC(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-CCDZVGGQSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.663

> <EXACT_MASS>
402.349780721

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.61099063734379

> <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)-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>
122.46819999999997

> <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)-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    NULL                                                        
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    8663.3658667.399   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    8666.0338667.399   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
27-Hydroxycholesterol	ChEBI
Cholest-5-ene-3beta,26-diol	ChEBI
Cholest-5-ene-3beta,27-diol	ChEBI
Cholest-5-ene-3b,26-diol	Generator
Cholest-5-ene-3β,26-diol	Generator
Cholest-5-ene-3b,27-diol	Generator
Cholest-5-ene-3β,27-diol	Generator
(25R)-Cholest-5-ene-3 beta,26-diol	MeSH
5-Cholestene-3 beta,27-diol	MeSH
(3 beta,25R)-Cholest-5-ene-3,26-diol	MeSH
26-Hydroxycholesterol, (25R)	MeSH
(25R)-26-Hydroxycholesterol	MeSH
Cholest-5-ene-3 beta,27-diol	MeSH

Chemical Formula

C₂₇H₄₆O₂

Average Mass

402.6630 Da

Monoisotopic Mass

402.34978 Da

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-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)-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)CCCC(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-CCDZVGGQSA-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
Homo sapiens	LOTUS Database	35616633

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-hydroxy steroid (CHEBI:17703 )
oxysterol (CHEBI:17703 )
Cholesterol and derivatives (C15610 )
Cholesterol and derivatives (LMST01010057 )

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	51.61 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

HMDB0062328

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C15610

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

99470

PDB ID

Not Available

ChEBI ID

17703

Good Scents ID

Not Available

References

General References

Crow JA, Herring KL, Xie S, Borazjani A, Potter PM, Ross MK: Inhibition of carboxylesterase activity of THP1 monocytes/macrophages and recombinant human carboxylesterase 1 by oxysterols and fatty acids. Biochim Biophys Acta. 2010 Jan;1801(1):31-41. doi: 10.1016/j.bbalip.2009.09.002. Epub 2009 Sep 15. [PubMed:19761868 ]
LOTUS database [Link]

Showing NP-Card for 26-hydroxycholesterol (NP0286761)

MOL for NP0286761 (26-hydroxycholesterol)

3D MOL for NP0286761 (26-hydroxycholesterol)

3D SDF for NP0286761 (26-hydroxycholesterol)

3D-SDF for NP0286761 (26-hydroxycholesterol)

PDB for NP0286761 (26-hydroxycholesterol)

3D PDB for NP0286761 (26-hydroxycholesterol)

SMILES for NP0286761 (26-hydroxycholesterol)

INCHI for NP0286761 (26-hydroxycholesterol)

Structure for NP0286761 (26-hydroxycholesterol)

3D Structure for NP0286761 (26-hydroxycholesterol)