NP-MRD: Showing NP-Card for 7a-Hydroxy-cholestene-3-one (NP0086836)

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Record Information

Version

2.0

Created at

2022-05-11 16:32:22 UTC

Updated at

2022-05-11 16:32:22 UTC

NP-MRD ID

NP0086836

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7a-Hydroxy-cholestene-3-one

Description

7A-Hydroxy-cholestene-3-one, also known as cholest-4-en-7alpha-ol-3-one or 7 alpha-3ox-C, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7a-hydroxy-cholestene-3-one is considered to be a bile acid lipid molecule. Analysis of 7a-Hydroxycholestene-3-one (HCO) in serum may serve as a novel, simple, and sensitive method for the detection of bile acid malabsorption in patients with chronic diarrhea of unknown origin (PMID 9952217 ). 7A-Hydroxy-cholestene-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, 7a-hydroxy-cholestene-3-one participates in a number of enzymatic reactions. In particular, 7a-hydroxy-cholestene-3-one can be converted into 7a-hydroxy-5b-cholestan-3-one through the action of the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase. In addition, 7a-hydroxy-cholestene-3-one can be biosynthesized from 7a-hydroxycholesterol; which is catalyzed by the enzyme 3 beta-hydroxysteroid dehydrogenase type 7. 7a-Hydroxy-cholestene-3-one is found in Trypanosoma brucei. 7a-Hydroxy-cholestene-3-one was first documented in 1985 (PMID: 3919058). In humans, 7a-hydroxy-cholestene-3-one is involved in cerebrotendinous xanthomatosis (ctx) (PMID: 9425924) (PMID: 2060639) (PMID: 3865344) (PMID: 3367085).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 02231219182D          

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M  END

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  Mrv0541 02231219182D          

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 14 21  1  6  0  0  0
 24 17  1  0  0  0  0
 19 18  1  0  0  0  0
 22 18  1  0  0  0  0
 27 20  1  0  0  0  0
 23 22  1  0  0  0  0
 25 23  1  0  0  0  0
 26 23  1  0  0  0  0
 27 24  1  0  0  0  0
 11 32  1  6  0  0  0
 33 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086836

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O2/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/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1

> <INCHI_KEY>
IOIZWEJGGCZDOL-RQDYSCIWSA-N

> <FORMULA>
C27H44O2

> <MOLECULAR_WEIGHT>
400.6371

> <EXACT_MASS>
400.334130652

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
50.60210025081398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
5.46

> <JCHEM_LOGP>
6.371370181666665

> <ALOGPS_LOGS>
-6.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.946034043249984

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.14119467931331

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6353871697001251

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
121.15759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.69e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7α-hydroxy-4-cholesten-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

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      14.376 -10.659   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.376 -12.169   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.712 -12.169   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.074 -12.910   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.380 -12.910   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.842 -10.186   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.074  -9.875   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.712 -10.659   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.842 -12.643   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.715 -11.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.074 -14.464   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.380 -14.464   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.712 -15.234   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.842  -8.617   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.376  -9.076   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.380 -11.400   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.077 -12.169   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.521  -8.572   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.219  -7.803   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.077 -15.234   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.436  -7.921   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.853  -7.773   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.186  -8.484   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.715 -12.910   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.186 -10.023   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.518  -7.655   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.715 -14.464   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      11.712 -13.709   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      13.074 -11.370   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      14.376 -13.709   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      15.842 -11.725   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0      14.263 -15.246   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.492 -15.246   0.000  0.00  0.00           O+0
CONECT    1    2    6    7   15                                             
CONECT    2    1    4    9   30                                             
CONECT    3    8    5    4   28                                             
CONECT    4    2    3   11   29                                             
CONECT    5    3   12   16   17                                             
CONECT    6    1   10   14   31                                             
CONECT    7    1    8                                                       
CONECT    8    3    7                                                       
CONECT    9    2   10                                                       
CONECT   10    6    9                                                       
CONECT   11    4   13   32                                                  
CONECT   12    5   20   13                                                  
CONECT   13   11   12                                                       
CONECT   14    6   19   21                                                  
CONECT   15    1                                                            
CONECT   16    5                                                            
CONECT   17    5   24                                                       
CONECT   18   19   22                                                       
CONECT   19   14   18                                                       
CONECT   20   12   27                                                       
CONECT   21   14                                                            
CONECT   22   18   23                                                       
CONECT   23   22   25   26                                                  
CONECT   24   17   27                                                       
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   20   24   33                                                  
CONECT   28    3                                                            
CONECT   29    4                                                            
CONECT   30    2                                                            
CONECT   31    6                                                            
CONECT   32   11                                                            
CONECT   33   27                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
7alpha-Hydroxy-4-cholesten-3-one	ChEBI
Cholest-4-en-7alpha-ol-3-one	ChEBI
7a-Hydroxy-4-cholesten-3-one	Generator
7Α-hydroxy-4-cholesten-3-one	Generator
Cholest-4-en-7a-ol-3-one	Generator
Cholest-4-en-7α-ol-3-one	Generator
7 alpha-3Ox-C	HMDB
7 alpha-Hydroxy-4-cholesten-3-one	HMDB
7-a-Hydroxy-4-cholesten-3-one	HMDB
7-a-Hydroxycholest-4-en-3-one	HMDB
7-alpha-Hydroxy-4-cholesten-3-one	HMDB
7-alpha-Hydroxycholest-4-en-3-one	HMDB
7-Hydroxycholest-4-en-3-one	HMDB
7a-Hydroxy-4-cholesten-3-one-12alpha	HMDB
7alpha-Hydroxycholest-4-en-3-one	HMDB
HCO	HMDB
Cholest-4-en-7 alpha-ol-3-one	HMDB
7-Hydroxy-4-cholesten-3-one	HMDB

Chemical Formula

C₂₇H₄₄O₂

Average Mass

400.6371 Da

Monoisotopic Mass

400.33413 Da

IUPAC Name

(1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

7α-hydroxy-4-cholesten-3-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C27H44O2/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/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1

InChI Key

IOIZWEJGGCZDOL-RQDYSCIWSA-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
Trypanosoma brucei	LOTUS Database	35616633

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-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
7-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:17899 )
7alpha-hydroxy steroid (CHEBI:17899 )
cholestanoid (CHEBI:17899 )
Cholesterol and derivatives (C05455 )
C27 bile acids, alcohols, and derivatives (LMST04030123 )

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	5.46	ALOGPS
logP	6.37	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	17.14	ChemAxon
pKa (Strongest Basic)	-0.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.16 m³·mol⁻¹	ChemAxon
Polarizability	50.6 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001993

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022786

KNApSAcK ID

Not Available

Chemspider ID

110306

KEGG Compound ID

C05455

BioCyc ID

Not Available

BiGG ID

45848

Wikipedia Link

Not Available

METLIN ID

6419

PubChem Compound

123743

PDB ID

Not Available

ChEBI ID

17899

Good Scents ID

Not Available

References

General References

Skrede S, Bjorkhem I, Buchmann MS, Hopen G, Fausa O: A novel pathway for biosynthesis of cholestanol with 7 alpha-hydroxylated C27-steroids as intermediates, and its importance for the accumulation of cholestanol in cerebrotendinous xanthomatosis. J Clin Invest. 1985 Feb;75(2):448-55. [PubMed:3919058 ]
Lin RC, Fillenwarth MJ, Du X: Cytotoxic effect of 7alpha-hydroxy-4-cholesten-3-one on HepG2 cells: hypothetical role of acetaldehyde-modified delta4-3-ketosteroid-5beta-reductase (the 37-kd-liver protein) in the pathogenesis of alcoholic liver injury in the rat. Hepatology. 1998 Jan;27(1):100-7. doi: 10.1002/hep.510270117. [PubMed:9425924 ]
Axelson M, Bjorkhem I, Reihner E, Einarsson K: The plasma level of 7 alpha-hydroxy-4-cholesten-3-one reflects the activity of hepatic cholesterol 7 alpha-hydroxylase in man. FEBS Lett. 1991 Jun 24;284(2):216-8. doi: 10.1016/0014-5793(91)80688-y. [PubMed:2060639 ]
Skrede S, Bjorkhem I: A novel route for the biosynthesis of cholestanol, and its significance for the pathogenesis of cerebrotendinous xanthomatosis. Scand J Clin Lab Invest Suppl. 1985;177:15-21. [PubMed:3865344 ]
Skrede S, Buchmann MS, Bjorkhem I: Hepatic 7 alpha-dehydroxylation of bile acid intermediates, and its significance for the pathogenesis of cerebrotendinous xanthomatosis. J Lipid Res. 1988 Feb;29(2):157-64. [PubMed:3367085 ]

Showing NP-Card for 7a-Hydroxy-cholestene-3-one (NP0086836)

MOL for NP0086836 (7a-Hydroxy-cholestene-3-one)

3D MOL for NP0086836 (7a-Hydroxy-cholestene-3-one)

3D SDF for NP0086836 (7a-Hydroxy-cholestene-3-one)

3D-SDF for NP0086836 (7a-Hydroxy-cholestene-3-one)

PDB for NP0086836 (7a-Hydroxy-cholestene-3-one)

3D PDB for NP0086836 (7a-Hydroxy-cholestene-3-one)

SMILES for NP0086836 (7a-Hydroxy-cholestene-3-one)

INCHI for NP0086836 (7a-Hydroxy-cholestene-3-one)

Structure for NP0086836 (7a-Hydroxy-cholestene-3-one)

3D Structure for NP0086836 (7a-Hydroxy-cholestene-3-one)