NP-MRD: Showing NP-Card for 7alpha,27-Dihydroxycholesterol (NP0087482)

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Record Information

Version

2.0

Created at

2022-05-11 16:50:53 UTC

Updated at

2022-05-11 16:50:53 UTC

NP-MRD ID

NP0087482

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7alpha,27-Dihydroxycholesterol

Description

7-A,27-Dihydroxycholesterol, also known as cholest-5-ene-3b,7a,26-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. Thus, 7-a,27-dihydroxycholesterol is considered to be a bile acid lipid molecule. 7-A,27-Dihydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, 7-a,27-dihydroxycholesterol participates in a number of enzymatic reactions. In particular, 7-a,27-dihydroxycholesterol can be biosynthesized from 27-hydroxycholesterol; which is mediated by the enzyme cholesterol 7-alpha-monooxygenase. In addition, 7-a,27-dihydroxycholesterol can be biosynthesized from 27-hydroxycholesterol through the action of the enzyme 25-hydroxycholesterol 7-alpha-hydroxylase. In humans, 7-a,27-dihydroxycholesterol is involved in cerebrotendinous xanthomatosis (ctx).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220362D          

 34 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 02231220362D          

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 18 27  1  0  0  0  0
 19 20  1  0  0  0  0
 19 31  1  0  0  0  0
 21 24  1  0  0  0  0
 22 29  1  0  0  0  0
 23 32  1  1  0  0  0
 24 30  1  0  0  0  0
 25 28  1  0  0  0  0
 25 30  1  0  0  0  0
 28 26  1  0  0  0  0
 26 29  1  0  0  0  0
 27 28  1  0  0  0  0
 27 33  1  6  0  0  0
 28  3  1  1  0  0  0
 26  2  1  6  0  0  0
 25  1  1  6  0  0  0
 24 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0087482

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h15,17-18,20-25,28-30H,5-14,16H2,1-4H3/t17?,18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1

> <INCHI_KEY>
RXMHNAKZMGJANZ-DTTSCKGMSA-N

> <FORMULA>
C27H46O3

> <MOLECULAR_WEIGHT>
418.6523

> <EXACT_MASS>
418.344695338

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
52.19183647090848

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol

> <ALOGPS_LOGP>
4.67

> <JCHEM_LOGP>
4.601306807

> <ALOGPS_LOGS>
-4.92

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.204233421519334

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.41832287471465

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7769845688142142

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
123.90669999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.07e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7α,27-dihydroxycholesterol

> <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  H   UNK     0      23.193 -22.209   0.000  0.00  0.00           H+0
HETATM    2  H   UNK     0      20.410 -22.321   0.000  0.00  0.00           H+0
HETATM    3  H   UNK     0      21.801 -20.187   0.000  0.00  0.00           H+0
HETATM    4  C   UNK     0      30.492 -13.509   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.991 -16.255   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.080 -20.110   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.350 -17.823   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.004 -15.614   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.510 -15.294   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.528 -17.079   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.451 -20.110   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.545 -21.356   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.412 -21.650   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.413 -19.340   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.746 -20.880   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.747 -18.570   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.746 -23.960   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.413 -23.960   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.955 -12.685   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.986 -13.830   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.021 -17.399   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.080 -23.190   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.412 -23.190   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      24.545 -18.864   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.081 -20.880   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.413 -20.880   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.747 -23.190   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.747 -21.650   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      19.080 -21.650   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.081 -19.340   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      26.449 -13.005   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      15.079 -23.960   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      23.081 -23.960   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0      25.809 -18.907   0.000  0.00  0.00           H+0
CONECT    1   25                                                            
CONECT    2   26                                                            
CONECT    3   28                                                            
CONECT    4   20                                                            
CONECT    5   21                                                            
CONECT    6   29                                                            
CONECT    7   30                                                            
CONECT    8    9   10                                                       
CONECT    9    8   20                                                       
CONECT   10    8   21                                                       
CONECT   11   24   12                                                       
CONECT   12   11   25                                                       
CONECT   13   15   23                                                       
CONECT   14   26   16                                                       
CONECT   15   13   29                                                       
CONECT   16   14   30                                                       
CONECT   17   23   22                                                       
CONECT   18   22   27                                                       
CONECT   19   20   31                                                       
CONECT   20    4    9   19                                                  
CONECT   21    5   10   24                                                  
CONECT   22   17   18   29                                                  
CONECT   23   13   17   32                                                  
CONECT   24   11   21   30   34                                             
CONECT   25   12   28   30    1                                             
CONECT   26   14   28   29    2                                             
CONECT   27   18   28   33                                                  
CONECT   28   25   26   27    3                                             
CONECT   29    6   15   22   26                                             
CONECT   30    7   16   24   25                                             
CONECT   31   19                                                            
CONECT   32   23                                                            
CONECT   33   27                                                            
CONECT   34   24                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
5-Cholestene-3beta,7alpha,26-triol	ChEBI
7-alpha,27-Dihydroxycholesterol	ChEBI
Cholest-5-ene-3beta,7alpha,26-triol	ChEBI
Cholest-5-ene-3beta,7alpha,27-triol	ChEBI
5-Cholestene-3b,7a,26-triol	Generator
5-Cholestene-3β,7α,26-triol	Generator
7-Α,27-dihydroxycholesterol	Generator
Cholest-5-ene-3b,7a,26-triol	Generator
Cholest-5-ene-3β,7α,26-triol	Generator
Cholest-5-ene-3b,7a,27-triol	Generator
Cholest-5-ene-3β,7α,27-triol	Generator
7alpha,26-Dihydroxycholesterol	HMDB
7alpha,27-Dihydroxycholesterol	HMDB
Cholest-5-ene-3,7,27-triol	HMDB
Cholest-5-ene-3- b,7-a,27-triol	HMDB
Cholest-5-ene-3-b,7-a,27-triol	HMDB
Cholest-5-ene-3-beta,7-alpha,27-triol	HMDB

Chemical Formula

C₂₇H₄₆O₃

Average Mass

418.6523 Da

Monoisotopic Mass

418.34470 Da

IUPAC Name

(1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol

Traditional Name

7α,27-dihydroxycholesterol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H46O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h15,17-18,20-25,28-30H,5-14,16H2,1-4H3/t17?,18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1

InChI Key

RXMHNAKZMGJANZ-DTTSCKGMSA-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

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

triol (CHEBI:18431 )
7alpha-hydroxy steroid (CHEBI:18431 )
26-hydroxy steroid (CHEBI:18431 )
oxysterol (CHEBI:18431 )
Cholesterol and derivatives (C06341 )
C27 bile acids, alcohols, and derivatives (LMST04030081 )

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	4.67	ALOGPS
logP	4.6	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	17.42	ChemAxon
pKa (Strongest Basic)	-0.78	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	6	ChemAxon
Refractivity	123.91 m³·mol⁻¹	ChemAxon
Polarizability	52.19 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	Yes	ChemAxon