NP-MRD: Showing NP-Card for 20alpha,22beta-Dihydroxycholesterol (NP0087625)

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Record Information

Version

2.0

Created at

2022-05-11 16:55:08 UTC

Updated at

2022-05-11 16:55:08 UTC

NP-MRD ID

NP0087625

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20alpha,22beta-Dihydroxycholesterol

Description

20A,22b-Dihydroxycholesterol, also known as not available, 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. 20A,22b-Dihydroxycholesterol is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, 20a,22b-dihydroxycholesterol participates in a number of enzymatic reactions. In particular, 20a,22b-dihydroxycholesterol can be converted into pregnenolone and 4-methylpentanal; which is catalyzed by the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In addition, 20a,22b-dihydroxycholesterol can be biosynthesized from 22b-hydroxycholesterol through the action of the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In humans, 20a,22b-dihydroxycholesterol is involved in the metabolic disorder called the apparent mineralocorticoid excess syndrome pathway.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220512D          

 34 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 02231220512D          

 34 37  0  0  1  0            999 V2000
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 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  6  0  0  0
 18 24  1  6  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  5 28  1  1  0  0  0
 12 29  1  1  0  0  0
  2 30  1  0  0  0  0
 10 31  1  6  0  0  0
 11 32  1  6  0  0  0
  9 33  1  1  0  0  0
 17 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0087625

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@]([H])([C@@](C)(O)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(O)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-IVMOZYHGSA-N

> <FORMULA>
C27H46O3

> <MOLECULAR_WEIGHT>
418.6523

> <EXACT_MASS>
418.344695338

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
51.503074676857274

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-2-[(1S,2R,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>
123.66009999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-[(1S,2R,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

> <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      28.560 -11.027   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.560 -12.567   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.894 -13.337   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.228 -12.567   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.228 -11.027   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.894 -10.257   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.561 -13.337   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.895 -12.567   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.895 -11.027   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.561 -10.257   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      35.229 -10.257   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.229  -8.717   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.895  -7.947   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.561  -8.717   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      36.693 -10.733   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.599  -9.487   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      36.693  -8.241   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      37.168  -6.782   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      36.141  -5.641   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      38.669  -6.463   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      39.696  -7.603   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      41.197  -7.284   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      39.143  -5.003   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      37.642  -5.322   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      42.224  -8.424   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      43.725  -8.105   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      41.749  -9.884   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      31.228  -9.493   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      35.389  -7.191   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      27.231 -13.334   0.000  0.00  0.00           O+0
HETATM   31  H   UNK     0      32.567 -11.575   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      35.389 -11.783   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      33.895  -9.493   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      38.209  -8.001   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   28                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   33                                             
CONECT   10    9    5   14   31                                             
CONECT   11    9   12   15   32                                             
CONECT   12   11   13   17   29                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18   34                                             
CONECT   18   17   19   20   24                                             
CONECT   19   18                                                            
CONECT   20   18   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   25                                                       
CONECT   23   20                                                            
CONECT   24   18                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28    5                                                            
CONECT   29   12                                                            
CONECT   30    2                                                            
CONECT   31   10                                                            
CONECT   32   11                                                            
CONECT   33    9                                                            
CONECT   34   17                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
20alpha,22beta-Dihydroxycholesterol	HMDB

Chemical Formula

C₂₇H₄₆O₃

Average Mass

418.6523 Da

Monoisotopic Mass

418.34470 Da

IUPAC Name

(2R,3R)-2-[(1S,2R,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

(2R,3R)-2-[(1S,2R,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

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@]([H])([C@@](C)(O)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(O)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-IVMOZYHGSA-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 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
Hydroxysteroid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	51.5 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

HMDB0006763

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB024066

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05501

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477897

PDB ID

Not Available

ChEBI ID

1294

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 20alpha,22beta-Dihydroxycholesterol (NP0087625)

MOL for NP0087625 (20alpha,22beta-Dihydroxycholesterol)

3D MOL for NP0087625 (20alpha,22beta-Dihydroxycholesterol)

3D SDF for NP0087625 (20alpha,22beta-Dihydroxycholesterol)

3D-SDF for NP0087625 (20alpha,22beta-Dihydroxycholesterol)

PDB for NP0087625 (20alpha,22beta-Dihydroxycholesterol)

3D PDB for NP0087625 (20alpha,22beta-Dihydroxycholesterol)

SMILES for NP0087625 (20alpha,22beta-Dihydroxycholesterol)

INCHI for NP0087625 (20alpha,22beta-Dihydroxycholesterol)

Structure for NP0087625 (20alpha,22beta-Dihydroxycholesterol)

3D Structure for NP0087625 (20alpha,22beta-Dihydroxycholesterol)