NP-MRD: Showing NP-Card for 4-alpha-Methyl-5-alpha-cholest-7-en-3-one (NP0091514)

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Record Information

Version

2.0

Created at

2022-05-11 18:40:13 UTC

Updated at

2022-05-11 18:40:13 UTC

NP-MRD ID

NP0091514

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-alpha-Methyl-5-alpha-cholest-7-en-3-one

Description

4-Alpha-Methyl-5-alpha-cholest-7-en-3-one, also known as (4alpha,5alpha)-4-methylcholest-7-en-3-one, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 4-alpha-methyl-5-alpha-cholest-7-en-3-one is considered to be a sterol lipid molecule. 4-Alpha-Methyl-5-alpha-cholest-7-en-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Alpha-Methyl-5-alpha-cholest-7-en-3-one exists in all eukaryotes, ranging from yeast to humans. This enzyme is responsible for the reduction of the keto group on the C-3 of sterols.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 02241201472D          

 33 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END

  Mrv0541 02241201472D          

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 18 15  1  0  0  0  0
 17 16  1  0  0  0  0
 24 19  1  0  0  0  0
 21 20  1  0  0  0  0
 20 25  2  0  0  0  0
 28 24  1  0  0  0  0
 29 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0091514

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])[C@H](C)C(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h10,18-20,22-25H,7-9,11-17H2,1-6H3/t19-,20+,22-,23+,24+,25+,27-,28+/m1/s1

> <INCHI_KEY>
OWKGVPXWOHLTSL-LIUJFMQASA-N

> <FORMULA>
C28H46O

> <MOLECULAR_WEIGHT>
398.6642

> <EXACT_MASS>
398.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
51.341004476348076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-one

> <ALOGPS_LOGP>
7.41

> <JCHEM_LOGP>
7.863376110666668

> <ALOGPS_LOGS>
-7.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.412075660595985

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
124.16289999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.84e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      19.584 -17.916   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.579 -15.599   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.910 -17.149   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.579 -17.149   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.584 -19.450   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.236 -17.916   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.905 -14.832   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.231 -12.515   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.557 -13.298   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.236 -14.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.258 -20.216   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.905 -13.298   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.258 -17.149   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.910 -15.599   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.231 -17.149   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.910 -20.216   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.236 -19.450   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.231 -15.599   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.883 -12.515   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.916 -19.450   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.916 -17.916   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.584 -16.366   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.579 -14.065   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      30.225 -13.298   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      15.574 -20.232   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      18.258 -21.766   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.579 -12.515   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      31.552 -12.515   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      30.225 -14.832   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0      19.600 -21.047   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      24.905 -16.318   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      20.910 -18.698   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      23.579 -18.698   0.000  0.00  0.00           H+0
CONECT    1    3    5   13   22                                             
CONECT    2   10    7   23    4                                             
CONECT    3    1    6   14   32                                             
CONECT    4    2    6   15   33                                             
CONECT    5    1   11   16   30                                             
CONECT    6    3    4   17                                                  
CONECT    7    2   12   31   18                                             
CONECT    8   12    9                                                       
CONECT    9    8   19                                                       
CONECT   10    2   14                                                       
CONECT   11    5   26   20                                                  
CONECT   12    7    8   27                                                  
CONECT   13    1   21                                                       
CONECT   14    3   10                                                       
CONECT   15    4   18                                                       
CONECT   16    5   17                                                       
CONECT   17    6   16                                                       
CONECT   18    7   15                                                       
CONECT   19    9   24                                                       
CONECT   20   11   21   25                                                  
CONECT   21   13   20                                                       
CONECT   22    1                                                            
CONECT   23    2                                                            
CONECT   24   19   28   29                                                  
CONECT   25   20                                                            
CONECT   26   11                                                            
CONECT   27   12                                                            
CONECT   28   24                                                            
CONECT   29   24                                                            
CONECT   30    5                                                            
CONECT   31    7                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(4alpha,5alpha)-4-Methylcholest-7-en-3-one	ChEBI
4alpha-Methyl-5alpha-cholest-7-en-3-one	ChEBI
(4a,5a)-4-Methylcholest-7-en-3-one	Generator
(4Α,5α)-4-methylcholest-7-en-3-one	Generator
4a-Methyl-5a-cholest-7-en-3-one	Generator
4Α-methyl-5α-cholest-7-en-3-one	Generator
4-a-Methyl-5-a-cholest-7-en-3-one	Generator
4-Α-methyl-5-α-cholest-7-en-3-one	Generator

Chemical Formula

C₂₈H₄₆O

Average Mass

398.6642 Da

Monoisotopic Mass

398.35487 Da

IUPAC Name

(1R,2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-one

Traditional Name

(1R,2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])[C@H](C)C(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C28H46O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h10,18-20,22-25H,7-9,11-17H2,1-6H3/t19-,20+,22-,23+,24+,25+,27-,28+/m1/s1

InChI Key

OWKGVPXWOHLTSL-LIUJFMQASA-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

Substituents

Cholesterol-skeleton
3-oxo-5-alpha-steroid
Oxosteroid
3-oxosteroid
3-oxo-delta-7-steroid
Delta-7-steroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo Delta(7)-steroid (CHEBI:16495 )
Cholesterol and derivatives (C04453 )
Cholesterol and derivatives (LMST01010208 )

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	7.41	ALOGPS
logP	7.86	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	124.16 m³·mol⁻¹	ChemAxon
Polarizability	51.34 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