NP-MRD: Showing NP-Card for 22beta-Hydroxycholesterol (NP0087120)

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Record Information

Version

1.0

Created at

2022-05-11 16:40:40 UTC

Updated at

2022-05-11 16:40:40 UTC

NP-MRD ID

NP0087120

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22beta-Hydroxycholesterol

Description

22B-Hydroxycholesterol, also known as cholest-5-en-3b,22R-diol or 22(R)OH cholesterol, 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, 22b-hydroxycholesterol is considered to be a sterol lipid molecule. An oxysterol that is the 22R-hydroxy derivative of cholesterol. 22B-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 22B-Hydroxycholesterol exists in all eukaryotes, ranging from yeast to humans. Within humans, 22b-hydroxycholesterol participates in a number of enzymatic reactions. In particular, 22b-hydroxycholesterol can be converted into 20a,22b-dihydroxycholesterol; which is catalyzed by the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In addition, 22b-hydroxycholesterol can be biosynthesized from cholesterol; which is catalyzed by the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. 22beta-Hydroxycholesterol is found in Narthecium ossifragum and Ruscus aculeatus. It was first documented in 1992 (PMID: 1525048). In humans, 22b-hydroxycholesterol is involved in the metabolic disorder called the 11-beta-hydroxylase deficiency (cyp11b1) pathway (PMID: 14701824) (PMID: 12437582) (PMID: 16227152) (PMID: 10692116).

Structure

MOL 3D MOL SDF PDB SMILES InChI

HMDB04035.mol
  Mrv0541 02231219512D          

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M  END

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HMDB04035.mol
  Mrv0541 02231219512D          

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 10 24  1  6  0  0  0
 19 25  1  6  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 26 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0087120

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O2/c1-17(2)6-11-25(29)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+/m0/s1

> <INCHI_KEY>
RZPAXNJLEKLXNO-GFKLAVDKSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.6529

> <EXACT_MASS>
402.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
50.76953840343177

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15S)-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

> <ALOGPS_LOGP>
5.69

> <JCHEM_LOGP>
5.804124233666668

> <ALOGPS_LOGS>
-5.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.477856532809838

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7338943961064351

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
122.20899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.53e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
22R-hydroxycholesterol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB04035.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.277  -3.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.277  -4.902   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.943  -5.672   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.610  -4.902   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.610  -3.362   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.943  -2.592   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.276  -5.672   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.942  -4.902   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.942  -3.362   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.276  -2.592   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.391  -2.592   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.391  -1.052   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.942  -0.282   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.276  -1.052   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.856  -3.067   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.761  -1.822   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.856  -0.576   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.553   0.480   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.332   0.889   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      -0.942  -1.822   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0      -3.610  -1.822   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -7.611  -5.672   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       0.391  -4.132   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.276  -4.132   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       1.243   1.978   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.838   1.209   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.237   2.697   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.725   3.095   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.123   4.583   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.034   5.672   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.611   4.981   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.927   0.120   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   21                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   20                                             
CONECT   10    9    5   14   24                                             
CONECT   11    9   12   15   23                                             
CONECT   12   11   13   17   18                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   19                                                  
CONECT   18   12                                                            
CONECT   19   17   25   26                                                  
CONECT   20    9                                                            
CONECT   21    5                                                            
CONECT   22    2                                                            
CONECT   23   11                                                            
CONECT   24   10                                                            
CONECT   25   19                                                            
CONECT   26   19   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   26                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(3beta,22R)-Cholest-5-ene-3,22-diol	ChEBI
22beta-Hydroxycholesterol	ChEBI
22R-Hydroxycholesterol	ChEBI
Cholest-5-en-3beta,22R-diol	ChEBI
(22R)-22-Hydroxycholesterol	Kegg
(3b,22R)-Cholest-5-ene-3,22-diol	Generator
(3Β,22R)-cholest-5-ene-3,22-diol	Generator
22Β-hydroxycholesterol	Generator
Cholest-5-en-3b,22R-diol	Generator
Cholest-5-en-3β,22R-diol	Generator
22-Hydroxycholesterol, (3beta,20R,22R)-isomer	HMDB
22-Hydroxycholesterol, (3beta,20R,22S)-isomer	HMDB
Cholest-5-ene-3beta,22-diol	HMDB
22(R)-Hydroxycholesterol	HMDB
22-Hydroxycholesterol, (3beta,22S)-isomer	HMDB
22(R)OH Cholesterol	HMDB
22-Hydroxycholesterol	HMDB
22-Hydroxycholesterol, (3beta,22R)-isomer	HMDB
22S-Hydroxycholesterol	HMDB

Chemical Formula

C₂₇H₄₆O₂

Average Mass

402.6529 Da

Monoisotopic Mass

402.34978 Da

IUPAC Name

(1S,2R,5S,10S,11S,14R,15S)-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

Traditional Name

22R-hydroxycholesterol

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H]([C@H](C)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C27H46O2/c1-17(2)6-11-25(29)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+/m0/s1

InChI Key

RZPAXNJLEKLXNO-GFKLAVDKSA-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
Narthecium ossifragum	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Ruscus aculeatus	LOTUS Database	35616633
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

Cholesterol
Cholesterol-skeleton
Cholestane-skeleton
Dihydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
Hydroxysteroid
3-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
3-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

oxysterol (CHEBI:67237 )
22-hydroxy steroid (CHEBI:67237 )
Cholesterol and derivatives (C05502 )
Cholesterol and derivatives (LMST01010086 )

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	5.69	ALOGPS
logP	5.8	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-0.73	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	50.77 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

HMDB0004035

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023285

KNApSAcK ID

Not Available

Chemspider ID

146693

KEGG Compound ID

C05502

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7006

PubChem Compound

167685

PDB ID

Not Available

ChEBI ID

67237

Good Scents ID

Not Available

References

General References

Haidar B, Denis M, Marcil M, Krimbou L, Genest J Jr: Apolipoprotein A-I activates cellular cAMP signaling through the ABCA1 transporter. J Biol Chem. 2004 Mar 12;279(11):9963-9. doi: 10.1074/jbc.M313487200. Epub 2003 Dec 29. [PubMed:14701824 ]
Yao ZX, Brown RC, Teper G, Greeson J, Papadopoulos V: 22R-Hydroxycholesterol protects neuronal cells from beta-amyloid-induced cytotoxicity by binding to beta-amyloid peptide. J Neurochem. 2002 Dec;83(5):1110-9. doi: 10.1046/j.1471-4159.2002.01202.x. [PubMed:12437582 ]
Matsuzaki J, Tsuji T, Imazeki I, Ikeda H, Nishimura T: Immunosteroid as a regulator for Th1/Th2 balance: its possible role in autoimmune diseases. Autoimmunity. 2005 Aug;38(5):369-75. doi: 10.1080/08916930500124122. [PubMed:16227152 ]
Tuckey RC: Cholesterol side-chain cleavage by mitochondria from the human placenta. Studies using hydroxycholesterols as substrates. J Steroid Biochem Mol Biol. 1992 Sep;42(8):883-90. doi: 10.1016/0960-0760(92)90097-3. [PubMed:1525048 ]
Hanley K, Ng DC, He SS, Lau P, Min K, Elias PM, Bikle DD, Mangelsdorf DJ, Williams ML, Feingold KR: Oxysterols induce differentiation in human keratinocytes and increase Ap-1-dependent involucrin transcription. J Invest Dermatol. 2000 Mar;114(3):545-53. doi: 10.1046/j.1523-1747.2000.00895.x. [PubMed:10692116 ]

Showing NP-Card for 22beta-Hydroxycholesterol (NP0087120)

MOL for NP0087120 (22beta-Hydroxycholesterol)

3D MOL for NP0087120 (22beta-Hydroxycholesterol)

3D SDF for NP0087120 (22beta-Hydroxycholesterol)

3D-SDF for NP0087120 (22beta-Hydroxycholesterol)

PDB for NP0087120 (22beta-Hydroxycholesterol)

3D PDB for NP0087120 (22beta-Hydroxycholesterol)

SMILES for NP0087120 (22beta-Hydroxycholesterol)

INCHI for NP0087120 (22beta-Hydroxycholesterol)

Structure for NP0087120 (22beta-Hydroxycholesterol)

3D Structure for NP0087120 (22beta-Hydroxycholesterol)