NP-MRD: Showing NP-Card for 3a,7a-Dihydroxy-5b-cholestane (NP0087670)

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Record Information

Version

2.0

Created at

2022-05-11 16:56:26 UTC

Updated at

2022-05-11 16:56:26 UTC

NP-MRD ID

NP0087670

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a,7a-Dihydroxy-5b-cholestane

Description

3A,7a-Dihydroxy-5b-cholestane, also known as dihydroxycoprostane or 5b-cholestane-3a,7a-diol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 3a,7a-dihydroxy-5b-cholestane is considered to be a bile acid lipid molecule. 3A,7a-Dihydroxy-5b-cholestane is an intermediate in bile acid synthesis. 3A,7a-Dihydroxy-5b-cholestane is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, 3a,7a-dihydroxy-5b-cholestane participates in a number of enzymatic reactions. In particular, 3a,7a-dihydroxy-5b-cholestane can be biosynthesized from 7a-hydroxy-5b-cholestan-3-one through the action of the enzyme aldo-keto reductase family 1 member C4. In addition, 3a,7a-dihydroxy-5b-cholestane can be converted into 3 alpha,7 alpha,26-trihydroxy-5beta-cholestane; which is catalyzed by the enzyme sterol 26-hydroxylase, mitochondrial. In humans, 3a,7a-dihydroxy-5b-cholestane is involved in cerebrotendinous xanthomatosis (ctx). 3A,7a-Dihydroxy-5b-cholestane is a potentially toxic compound. Bile acids have potent toxic properties (e.G., Membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis.

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv0541 02231220552D          
 
 34 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END

 
  Mrv0541 02231220552D          
 
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  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  1  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  1  0  0  0  0
 11 15  1  0  0  0  0
 11 16  1  0  0  0  0
 11 17  1  1  0  0  0
 14 18  1  0  0  0  0
 14 19  1  6  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 18 22  1  0  0  0  0
 20 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
 13 15  1  0  0  0  0
 21 23  1  0  0  0  0
  1 29  1  6  0  0  0
  2 30  1  1  0  0  0
  5 31  1  6  0  0  0
  7 32  1  6  0  0  0
 15 33  1  1  0  0  0
  1  2  1  0  0  0  0
  6 34  1  6  0  0  0
  1  3  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087670

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H48O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h17-25,28-29H,6-16H2,1-5H3/t18-,19+,20-,21-,22+,23+,24-,25+,26+,27-/m1/s1

> <INCHI_KEY>
APYVEUGLZHAHDJ-TVRYRFOISA-N

> <FORMULA>
C27H48O2

> <MOLECULAR_WEIGHT>
404.6688

> <EXACT_MASS>
404.36543078

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
51.58902382934349

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5R,7S,9R,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9-diol

> <ALOGPS_LOGP>
5.88

> <JCHEM_LOGP>
6.209703715000002

> <ALOGPS_LOGS>
-6.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.296339908541825

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5356602821376611

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
121.35899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.14e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5β-cholestane-3α,7α-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      21.444 -15.019   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.110 -15.788   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.444 -13.479   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.111 -15.019   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.783 -15.019   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.103 -17.328   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.791 -12.709   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.110 -12.709   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.437 -12.099   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.111 -13.479   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.436 -15.788   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.783 -13.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.783 -18.098   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.791 -11.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.436 -17.328   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.109 -15.019   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.422 -14.249   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.151 -10.387   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.060  -9.744   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.109 -18.098   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.775 -15.788   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.512 -11.176   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.775 -17.328   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.872 -10.387   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.428 -18.098   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      28.239 -11.176   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      29.599 -10.393   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      28.232 -12.749   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      21.517 -16.591   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      20.097 -14.249   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      18.769 -16.558   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      24.476 -11.793   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      17.427 -18.916   0.000  0.00  0.00           H+0
HETATM   34  O   UNK     0      21.478 -18.122   0.000  0.00  0.00           O+0
CONECT    1    4   29    2    3                                             
CONECT    2    5    6   30    1                                             
CONECT    3    7    8    9    1                                             
CONECT    4    1   10                                                       
CONECT    5    2   11   12   31                                             
CONECT    6    2   13   34                                                  
CONECT    7    3   14   10   32                                             
CONECT    8    3   12                                                       
CONECT    9    3                                                            
CONECT   10    4    7                                                       
CONECT   11    5   15   16   17                                             
CONECT   12    5    8                                                       
CONECT   13    6   15                                                       
CONECT   14    7   18   19                                                  
CONECT   15   11   20   13   33                                             
CONECT   16   11   21                                                       
CONECT   17   11                                                            
CONECT   18   14   22                                                       
CONECT   19   14                                                            
CONECT   20   15   23                                                       
CONECT   21   16   23                                                       
CONECT   22   18   24                                                       
CONECT   23   20   25   21                                                  
CONECT   24   22   26                                                       
CONECT   25   23                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    1                                                            
CONECT   30    2                                                            
CONECT   31    5                                                            
CONECT   32    7                                                            
CONECT   33   15                                                            
CONECT   34    6                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
3alpha,7alpha-Dihydroxy-5beta-cholestane	ChEBI
Dihydroxycoprostane	ChEBI
5beta-Cholestane-3alpha,7alpha-diol	Kegg
3Α,7α-dihydroxy-5β-cholestane	Generator
5b-Cholestane-3a,7a-diol	Generator
5Β-cholestane-3α,7α-diol	Generator
3,7-Dihydroxy-5-cholestane	HMDB
3,7-Dihydroxycholestane	HMDB
5alpha-Cholestane-3beta,7beta-diol	HMDB
Dihydroxycoprostane, (3alpha,5alpha,7alpha)-isomer	HMDB
Dihydroxycoprostane, (3beta,5alpha,7alpha)-isomer	HMDB

Chemical Formula

C₂₇H₄₈O₂

Average Mass

404.6688 Da

Monoisotopic Mass

404.36543 Da

IUPAC Name

(1S,2S,5R,7S,9R,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9-diol

Traditional Name

5β-cholestane-3α,7α-diol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H48O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h17-25,28-29H,6-16H2,1-5H3/t18-,19+,20-,21-,22+,23+,24-,25+,26+,27-/m1/s1

InChI Key

APYVEUGLZHAHDJ-TVRYRFOISA-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 cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Not Available

Substituents

Not Available

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	5.88	ALOGPS
logP	6.21	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-0.54	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	121.36 m³·mol⁻¹	ChemAxon
Polarizability	51.59 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