NP-MRD: Showing NP-Card for 5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol (NP0136907)

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Record Information

Version

2.0

Created at

2022-05-12 15:26:46 UTC

Updated at

2022-05-12 15:26:46 UTC

NP-MRD ID

NP0136907

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol

Description

5Beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol, also known as cholestane-3,7,12,25-tetrol or 3α,7α,12α,25-tetrahydroxycoprostane, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 5beta-cholestane-3alpha,7alpha,12alpha,25-tetrol is considered to be a bile acid lipid molecule. 5Beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. The enhanced cholesterol 7 alpha-hydroxylase (CYP7A1) expression in CYP27 deficiency may be the result of a decreased flux of bile acids and bile alcohols into the liver, while production of FXR-activating 5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol is increased (PMID: 15145977 ). Bile acid synthesis from cholesterol is tightly regulated via a feedback mechanism mediated by the farnesoid X receptor (FXR), a nuclear receptor activated by bile acids. In cerebrotendinous xanthomatosis (CTX), a bile acid synthesis disorder caused by sterol 27-hydroxylase (CYP27) deficiency, early intermediates and cholestanol accumulate in a variety of tissues, and glucuronides of 25-hydroxylated bile alcohols are released in bile, blood, and urine (PMID: 11181760 ). 5β-Cholestane-3α,7α,12α,25-tetrol is an intermediate in the bile acid synthetic pathway, and is secreted into the bile and urine following glucuronidation. Synthesis via the classic pathway is initiated by a series of cholesterol ring modifications and followed by the side chain cleavage. It does not undergo enterohepatic circulation.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304202022182D          

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M  END

     RDKit          3D

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M  END

  Mrv1652304202022182D          

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10004.338310002.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.037210001.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.212210001.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.050410002.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479710001.3024    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.264910001.8724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11  3  1  6  0  0  0
 16  1  1  6  0  0  0
  9 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14  4  1  1  0  0  0
 13  5  1  1  0  0  0
 19 13  1  0  0  0  0
 16 20  1  0  0  0  0
 19  6  1  6  0  0  0
 20  8  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 35  1  6  0  0  0
 26 27  1  0  0  0  0
 26 34  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 17 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21  2  1  1  0  0  0
 22  7  1  6  0  0  0
 17 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0136907

> <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])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C27H48O4/c1-16(7-6-11-25(2,3)31)19-8-9-20-24-21(15-23(30)27(19,20)5)26(4)12-10-18(28)13-17(26)14-22(24)29/h16-24,28-31H,6-15H2,1-5H3/t16-,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1

> <INCHI_KEY>
NTIXPPFPXLYJCT-RNUSRIHUSA-N

> <FORMULA>
C27H48O4

> <MOLECULAR_WEIGHT>
436.677

> <EXACT_MASS>
436.355260026

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
53.15902255791773

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
3.5077779629999988

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.530768466611097

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.2963399055959

> <JCHEM_PKA_STRONGEST_BASIC>
-0.12586972084882098

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
124.71059999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  O   UNK     0    8666.6268663.211   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8666.6228669.399   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.6418663.211   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8662.6358662.444   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0    8662.6358667.071   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0    8663.9648664.769   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8666.6228664.769   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0    8665.2938667.071   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0    8661.3058666.298   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8659.9718665.528   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8659.9718663.988   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.3058663.218   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.6328665.528   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.6328663.988   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.9658663.218   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.2998663.988   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.2948668.622   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.9618667.852   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8663.9618666.312   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8665.2948665.542   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.6288667.852   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.6288666.312   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.0938665.836   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.9988667.082   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.0938668.328   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8668.0938669.868   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8669.4298670.638   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8670.7618669.868   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8672.0978670.638   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8673.4338669.868   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8674.7658670.638   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8674.2038668.536   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0    8672.6638668.536   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0    8666.7618670.638   0.000  0.00  0.00           C+0
HETATM   35  H   UNK     0    8669.4298669.098   0.000  0.00  0.00           H+0
HETATM   36  O   UNK     0    8665.2948670.162   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   21                                                            
CONECT    3   11                                                            
CONECT    4   14                                                            
CONECT    5   13                                                            
CONECT    6   19                                                            
CONECT    7   22                                                            
CONECT    8   20                                                            
CONECT    9   10   13                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    3                                                  
CONECT   12   11   14                                                       
CONECT   13   14    9    5   19                                             
CONECT   14   13   15   12    4                                             
CONECT   15   14   16                                                       
CONECT   16   15    1   20                                                  
CONECT   17   18   21   36                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   13    6                                             
CONECT   20   19   16    8   22                                             
CONECT   21   22   25   17    2                                             
CONECT   22   21   23   20    7                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   26   35   21   24                                             
CONECT   26   25   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
CONECT   34   26                                                            
CONECT   35   25                                                            
CONECT   36   17                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
5b-Cholestane-3a,7a,12a,25-tetrol	Generator
5Β-cholestane-3α,7α,12α,25-tetrol	Generator
5 beta Cholestane-3 alpha,7 alpha,12 alpha,25-tetrol	HMDB
5 beta-Cholestane-3 beta,7 alpha,12 alpha,25-tetrol	HMDB
Cholestane-3,7,12,25-tetrol	HMDB
(3Α,5β,7α,12α)-cholestane-3,7,12,25-tetrol	HMDB
3Α,7α,12α,25-tetrahydroxycoprostane	HMDB
(3alpha,5beta,7alpha,12alpha)-Cholestane-3,7,12,25-tetrol	HMDB
3alpha,7alpha,12alpha,25-Tetrahydroxycoprostane	HMDB
5b-Cholestan-3a,7a,12a,25-tetrol	HMDB
5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol	Generator

Chemical Formula

C₂₇H₄₈O₄

Average Mass

436.6770 Da

Monoisotopic Mass

436.35526 Da

IUPAC Name

(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol

Traditional Name

(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol

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])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)(C)O

InChI Identifier

InChI=1S/C27H48O4/c1-16(7-6-11-25(2,3)31)19-8-9-20-24-21(15-23(30)27(19,20)5)26(4)12-10-18(28)13-17(26)14-22(24)29/h16-24,28-31H,6-15H2,1-5H3/t16-,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1

InChI Key

NTIXPPFPXLYJCT-RNUSRIHUSA-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

Not Available

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

Substituents

Cholesterol
Cholesterol-skeleton
25-hydroxysteroid
3-hydroxysteroid
12-hydroxysteroid
7-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Polyol
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C27 bile acids, alcohols, and derivatives (LMST04030037 )

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	3.64	ALOGPS
logP	3.51	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-0.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	124.71 m³·mol⁻¹	ChemAxon
Polarizability	53.16 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

HMDB0000524

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022092

KNApSAcK ID

Not Available

Chemspider ID

146751

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5509

PubChem Compound

167758

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol (NP0136907)

MOL for NP0136907 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

3D MOL for NP0136907 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

3D SDF for NP0136907 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

3D-SDF for NP0136907 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

PDB for NP0136907 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

3D PDB for NP0136907 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

SMILES for NP0136907 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

INCHI for NP0136907 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

Structure for NP0136907 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)

3D Structure for NP0136907 (5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol)