NP-MRD: Showing NP-Card for 4a-Methyl-5a-cholesta-8,24-dien-3-one (NP0334670)

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Record Information

Version

2.0

Created at

2024-09-10 19:25:23 UTC

Updated at

2024-09-10 19:25:23 UTC

NP-MRD ID

NP0334670

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4a-Methyl-5a-cholesta-8,24-dien-3-one

Description

4A-Methyl-5a-cholesta-8,24-dien-3-one, also known as 3-keto-4alpha-methyl-zymosterol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 4a-methyl-5a-cholesta-8,24-dien-3-one is considered to be a sterol lipid molecule. 4A-Methyl-5a-cholesta-8,24-dien-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231218512D          

 32 35  0  0  1  0            999 V2000
    8.7678   -8.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7678   -9.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4822   -9.5644    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1967   -9.1519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1967   -8.3269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4822   -7.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9112   -9.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6256   -9.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6256   -8.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9112   -7.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3401   -7.9144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3401   -7.0894    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6256   -6.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9112   -7.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1248   -8.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6097   -7.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1248   -6.8344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0533   -9.5644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4264   -6.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3797   -6.0498    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8277   -5.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1867   -5.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4416   -5.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2486   -4.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1967   -7.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4264   -8.7348    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8465   -6.6826    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2164   -9.9964    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5035   -4.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4822  -10.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3105   -3.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9514   -3.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  2  0  0  0  0
 12 19  1  1  0  0  0
 17 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 25  1  1  0  0  0
 11 26  1  6  0  0  0
 17 27  1  6  0  0  0
  4 28  1  6  0  0  0
 29 24  2  0  0  0  0
  3 30  1  6  0  0  0
 31 29  1  0  0  0  0
 32 29  1  0  0  0  0
M  END


  Mrv0541 02231218512D          

 32 35  0  0  1  0            999 V2000
    8.7678   -8.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7678   -9.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4822   -9.5644    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1967   -9.1519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1967   -8.3269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4822   -7.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9112   -9.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6256   -9.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6256   -8.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9112   -7.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3401   -7.9144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3401   -7.0894    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6256   -6.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9112   -7.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1248   -8.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6097   -7.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1248   -6.8344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0533   -9.5644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4264   -6.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3797   -6.0498    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8277   -5.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1867   -5.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4416   -5.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2486   -4.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1967   -7.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4264   -8.7348    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8465   -6.6826    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2164   -9.9964    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5035   -4.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4822  -10.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3105   -3.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9514   -3.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  2  0  0  0  0
 12 19  1  1  0  0  0
 17 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 25  1  1  0  0  0
 11 26  1  6  0  0  0
 17 27  1  6  0  0  0
  4 28  1  6  0  0  0
 29 24  2  0  0  0  0
  3 30  1  6  0  0  0
 31 29  1  0  0  0  0
 32 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334670

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O/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/h8,19-20,22-24H,7,9-17H2,1-6H3/t19-,20+,22-,23+,24+,27-,28+/m1/s1

> <INCHI_KEY>
DBPZYKHQDWKORQ-SINUOACOSA-N

> <FORMULA>
C28H44O

> <MOLECULAR_WEIGHT>
396.6484

> <EXACT_MASS>
396.33921603

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
50.94387677450595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one

> <ALOGPS_LOGP>
7.22

> <JCHEM_LOGP>
7.414138804666666

> <ALOGPS_LOGS>
-5.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.826726067146463

> <JCHEM_PKA_STRONGEST_BASIC>
-7.412274411747466

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
124.74629999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.64e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-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      16.367 -15.544   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.367 -17.084   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.700 -17.854   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.034 -17.084   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.034 -15.544   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.700 -14.774   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.368 -17.854   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.701 -17.084   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.701 -15.544   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.368 -14.774   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.035 -14.774   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.035 -13.234   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.701 -12.464   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.368 -13.234   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.500 -15.249   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.405 -14.004   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.500 -12.758   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      15.033 -17.854   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      23.196 -11.702   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.975 -11.293   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.945 -10.149   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.482 -10.973   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.958  -9.508   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      28.464  -9.188   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.034 -14.004   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      23.196 -16.305   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      25.847 -12.474   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      19.071 -18.660   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0      28.940  -7.723   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.700 -19.394   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      30.446  -7.403   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      27.909  -6.579   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4   30                                                  
CONECT    4    3    5    7   28                                             
CONECT    5    4    6   10   25                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    5   14                                                  
CONECT   11    9   12   15   26                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   20   27                                             
CONECT   18    2                                                            
CONECT   19   12                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   29                                                       
CONECT   25    5                                                            
CONECT   26   11                                                            
CONECT   27   17                                                            
CONECT   28    4                                                            
CONECT   29   24   31   32                                                  
CONECT   30    3                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(4alpha,5alpha)-4-Methylcholesta-8,24-dien-3-one	ChEBI
3-Keto-4alpha-methyl-zymosterol	ChEBI
3-Keto-4alpha-methylzymosterol	ChEBI
4alpha-Methyl-(5alpha)-cholesta-8,24-dien-3-one	ChEBI
(4a,5a)-4-Methylcholesta-8,24-dien-3-one	Generator
(4Α,5α)-4-methylcholesta-8,24-dien-3-one	Generator
3-Keto-4a-methyl-zymosterol	Generator
3-Keto-4α-methyl-zymosterol	Generator
3-Keto-4a-methylzymosterol	Generator
3-Keto-4α-methylzymosterol	Generator
4a-Methyl-(5a)-cholesta-8,24-dien-3-one	Generator
4Α-methyl-(5α)-cholesta-8,24-dien-3-one	Generator
4alpha-Methyl-5alpha-cholesta-8,24-dien-3-one	HMDB

Chemical Formula

C₂₈H₄₄O

Average Mass

396.6484 Da

Monoisotopic Mass

396.33922 Da

IUPAC Name

(2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one

Traditional Name

(2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C

InChI Identifier

InChI=1S/C28H44O/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/h8,19-20,22-24H,7,9-17H2,1-6H3/t19-,20+,22-,23+,24+,27-,28+/m1/s1

InChI Key

DBPZYKHQDWKORQ-SINUOACOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Cholesterol and derivatives (LMST01010237 )

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	7.22	ALOGPS
logP	7.41	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	19.83	ChemAxon
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	4	ChemAxon
Refractivity	124.75 m³·mol⁻¹	ChemAxon
Polarizability	50.94 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

HMDB0000981

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022350

KNApSAcK ID

Not Available

Chemspider ID

20059529

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5918

PubChem Compound

22298939

PDB ID

Not Available

ChEBI ID

136486

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4a-Methyl-5a-cholesta-8,24-dien-3-one (NP0334670)

MOL for NP0334670 (4a-Methyl-5a-cholesta-8,24-dien-3-one)

3D MOL for NP0334670 (4a-Methyl-5a-cholesta-8,24-dien-3-one)

3D SDF for NP0334670 (4a-Methyl-5a-cholesta-8,24-dien-3-one)

3D-SDF for NP0334670 (4a-Methyl-5a-cholesta-8,24-dien-3-one)

PDB for NP0334670 (4a-Methyl-5a-cholesta-8,24-dien-3-one)

3D PDB for NP0334670 (4a-Methyl-5a-cholesta-8,24-dien-3-one)

SMILES for NP0334670 (4a-Methyl-5a-cholesta-8,24-dien-3-one)

INCHI for NP0334670 (4a-Methyl-5a-cholesta-8,24-dien-3-one)

Structure for NP0334670 (4a-Methyl-5a-cholesta-8,24-dien-3-one)

3D Structure for NP0334670 (4a-Methyl-5a-cholesta-8,24-dien-3-one)