NP-MRD: Showing NP-Card for 20,22-dihydroxycholesterol (NP0142115)

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Record Information

Version

2.0

Created at

2022-09-01 20:34:55 UTC

Updated at

2022-09-01 20:34:55 UTC

NP-MRD ID

NP0142115

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20,22-dihydroxycholesterol

Description

(20R,22R)-20,22-dihydroxycholesterol, also known as 20alpha,22beta-dihydroxycholesterol or (20R,22R)-cholest-5-ene-3beta,20,22-triol, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. 20,22-dihydroxycholesterol is found in Mus musculus. Thus, (20R,22R)-20,22-dihydroxycholesterol is considered to be a sterol lipid molecule (20R,22R)-20,22-dihydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05031420582D          

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M  END

     RDKit          3D

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 22 13  1  0  0  0  0
 22 20  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  1  0  0  0  0
 25  3  1  6  0  0  0
 25 14  1  0  0  0  0
 25 18  1  0  0  0  0
 25 22  1  0  0  0  0
 26  4  1  6  0  0  0
 26 15  1  0  0  0  0
 26 21  1  0  0  0  0
 26 23  1  0  0  0  0
 27  5  1  6  0  0  0
 23 27  1  6  0  0  0
 27 24  1  0  0  0  0
 19 28  1  6  0  0  0
 24 29  1  6  0  0  0
 27 30  1  6  0  0  0
 19 31  1  1  0  0  0
 20 32  1  6  0  0  0
 21 33  1  1  0  0  0
 22 34  1  1  0  0  0
 23 35  1  1  0  0  0
 24 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0142115

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O3/c1-17(2)6-11-24(29)27(5,30)23-10-9-21-20-8-7-18-16-19(28)12-14-25(18,3)22(20)13-15-26(21,23)4/h7,17,19-24,28-30H,6,8-16H2,1-5H3/t19-,20-,21-,22-,23-,24+,25-,26-,27+/m0/s1

> <INCHI_KEY>
ISBSSBGEYIBVTO-TYKWNDPBSA-N

> <FORMULA>
C27H46O3

> <MOLECULAR_WEIGHT>
418.6523

> <EXACT_MASS>
418.344695338

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
51.975445302966435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.08

> <JCHEM_LOGP>
4.722778198666667

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.010299638705806

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.605227516123659

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972437702926297

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
123.66009999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20,22-dihydroxycholesterol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   31  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   17                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6   11   17                                                       
CONECT    7    8   18                                                       
CONECT    8    7   20                                                       
CONECT    9   10   21                                                       
CONECT   10    9   23                                                       
CONECT   11    6   24                                                       
CONECT   12   14   19                                                       
CONECT   13   15   22                                                       
CONECT   14   12   25                                                       
CONECT   15   13   26                                                       
CONECT   16   18   19                                                       
CONECT   17    1    2    6                                                  
CONECT   18    7   16   25                                                  
CONECT   19   12   16   28   31                                             
CONECT   20    8   21   22   32                                             
CONECT   21    9   20   26   33                                             
CONECT   22   13   20   25   34                                             
CONECT   23   10   26   27   35                                             
CONECT   24   11   27   29   36                                             
CONECT   25    3   14   18   22                                             
CONECT   26    4   15   21   23                                             
CONECT   27    5   23   24   30                                             
CONECT   28   19                                                            
CONECT   29   24                                                            
CONECT   30   27                                                            
CONECT   31   19                                                            
CONECT   32   20                                                            
CONECT   33   21                                                            
CONECT   34   22                                                            
CONECT   35   23                                                            
CONECT   36   24                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
(22R)-20alpha,22-Dihydroxycholesterol	ChEBI
20,22-Dihydroxycholesterol	ChEBI
20alpha,22beta-Dihydroxycholesterol	ChEBI
20alpha,22R-Dihydroxycholesterol	ChEBI
(22R)-20a,22-Dihydroxycholesterol	Generator
(22R)-20Α,22-dihydroxycholesterol	Generator
20a,22b-Dihydroxycholesterol	Generator
20Α,22β-dihydroxycholesterol	Generator
20a,22R-Dihydroxycholesterol	Generator
20Α,22R-dihydroxycholesterol	Generator
20,22-Dihydroxycholesterol, (3beta)-isomer	MeSH
(20R,22R)-Cholest-5-ene-3beta,20,22-triol	MeSH
20,22-Dihydroxycholesterol, (3beta,20S,20R)-isomer	MeSH
20,22-Dihydroxycholesterol, (3beta,22S)-isomer	MeSH
20 alpha,22R-Dihydroxycholesterol	MeSH

Chemical Formula

C₂₇H₄₆O₃

Average Mass

418.6523 Da

Monoisotopic Mass

418.34470 Da

IUPAC Name

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

Traditional Name

20,22-dihydroxycholesterol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H46O3/c1-17(2)6-11-24(29)27(5,30)23-10-9-21-20-8-7-18-16-19(28)12-14-25(18,3)22(20)13-15-26(21,23)4/h7,17,19-24,28-30H,6,8-16H2,1-5H3/t19-,20-,21-,22-,23-,24+,25-,26-,27+/m0/s1

InChI Key

ISBSSBGEYIBVTO-TYKWNDPBSA-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
Mus musculus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl 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

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cholestanoid (CHEBI:1294 )
3beta-sterol (CHEBI:1294 )
oxysterol (CHEBI:1294 )
20-hydroxy steroid (CHEBI:1294 )
22-hydroxy steroid (CHEBI:1294 )
Cholesterol and derivatives (C05501 )
Cholesterol and derivatives (LMST01010200 )

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	5.08	ALOGPS
logP	4.72	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	123.66 m³·mol⁻¹	ChemAxon
Polarizability	51.98 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

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

C05501

BioCyc ID

20A-20B-DIHYDROXY-CHOLESTEROL

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6453841

PDB ID

Not Available

ChEBI ID

1294

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 20,22-dihydroxycholesterol (NP0142115)

MOL for NP0142115 (20,22-dihydroxycholesterol)

3D MOL for NP0142115 (20,22-dihydroxycholesterol)

3D SDF for NP0142115 (20,22-dihydroxycholesterol)

3D-SDF for NP0142115 (20,22-dihydroxycholesterol)

PDB for NP0142115 (20,22-dihydroxycholesterol)

3D PDB for NP0142115 (20,22-dihydroxycholesterol)

SMILES for NP0142115 (20,22-dihydroxycholesterol)

INCHI for NP0142115 (20,22-dihydroxycholesterol)

Structure for NP0142115 (20,22-dihydroxycholesterol)

3D Structure for NP0142115 (20,22-dihydroxycholesterol)