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Showing NP-Card for 5beta-Cholestane (NP0049946)

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Record Information
Version2.0
Created at2022-03-17 21:20:40 UTC
Updated at2022-03-17 21:20:40 UTC
NP-MRD IDNP0049946
Secondary Accession NumbersNone
Natural Product Identification
Common Name5beta-Cholestane
Description5Beta-Cholestane, also known as β-cholestane or coprostane, belongs to the class of organic compounds known as cholestane steroids. These are steroids with a structure containing the 27-carbon cholestane skeleton. Thus, 5beta-cholestane is considered to be a sterol lipid molecule. 5Beta-Cholestane is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049946 (5beta-Cholestane)


  Mrv0541 02241222492D          

 32 35  0  0  1  0            999 V2000
   -1.5817    2.3820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2962    1.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0107    2.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0107    3.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962    3.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5817    3.2070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5817    4.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8672    3.6195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8672    4.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528    4.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    4.4445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6479    5.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463    4.6994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8312    4.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463    3.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    3.6195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1528    3.2070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1528    2.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8672    1.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463    5.5244    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0608    5.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7753    5.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4897    5.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042    5.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9187    5.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042    4.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6319    5.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5817    1.5570    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528    4.0320    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8672    2.7945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    2.7945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432    4.9129    0.0000 H   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
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 20 27  1  6  0  0  0
  1 28  1  1  0  0  0
 17 29  1  1  0  0  0
  8 30  1  6  0  0  0
 16 31  1  6  0  0  0
 13 32  1  6  0  0  0
M  END
Download

3D MOL for NP0049946 (5beta-Cholestane)

Download
3D SDF for NP0049946 (5beta-Cholestane)

  Mrv0541 02241222492D          

 32 35  0  0  1  0            999 V2000
   -1.5817    2.3820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2962    1.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0107    2.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0107    3.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962    3.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5817    3.2070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5817    4.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8672    3.6195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8672    4.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528    4.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    4.4445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6479    5.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463    4.6994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8312    4.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463    3.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    3.6195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1528    3.2070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1528    2.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8672    1.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463    5.5244    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0608    5.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7753    5.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4897    5.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042    5.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9187    5.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042    4.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6319    5.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5817    1.5570    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528    4.0320    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8672    2.7945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    2.7945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432    4.9129    0.0000 H   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
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 20 27  1  6  0  0  0
  1 28  1  1  0  0  0
 17 29  1  1  0  0  0
  8 30  1  6  0  0  0
 16 31  1  6  0  0  0
 13 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0049946

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H48/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h19-25H,6-18H2,1-5H3/t20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
XIIAYQZJNBULGD-CJPSHIORSA-N

> <FORMULA>
C27H48

> <MOLECULAR_WEIGHT>
372.67

> <EXACT_MASS>
372.375601536

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
49.92472035495692

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
7.66

> <JCHEM_LOGP>
8.905187039000003

> <ALOGPS_LOGS>
-7.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
118.09699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.61e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5β-cholestane

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0049946 (5beta-Cholestane)
Download
PDB for NP0049946 (5beta-Cholestane)
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      -2.953   4.446   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.286   3.676   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.620   4.446   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.620   5.986   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.286   6.756   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.953   5.986   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.953   7.526   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.619   6.756   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.619   8.296   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.285   9.066   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.049   8.296   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.209   9.828   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.513   8.772   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.418   7.526   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.513   6.280   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.049   6.756   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.285   5.986   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.285   4.446   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.619   3.676   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.513  10.312   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.847  11.082   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.181  10.312   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.514  11.082   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.848  10.312   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.182  11.082   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.848   8.772   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.180  11.082   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      -2.953   2.906   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.285   7.526   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.619   5.216   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.049   5.216   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.001   9.171   0.000  0.00  0.00           H+0
CONECT    1    2    6   19   28                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6    9   17   30                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   16                                             
CONECT   12   11                                                            
CONECT   13   11   14   20   32                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17   31                                             
CONECT   17   16    8   18   29                                             
CONECT   18   17   19                                                       
CONECT   19   18    1                                                       
CONECT   20   13   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   20                                                            
CONECT   28    1                                                            
CONECT   29   17                                                            
CONECT   30    8                                                            
CONECT   31   16                                                            
CONECT   32   13                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

Download
3D PDB for NP0049946 (5beta-Cholestane)
Download
SMILES for NP0049946 (5beta-Cholestane)
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CCCC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
Download
INCHI for NP0049946 (5beta-Cholestane)
InChI=1S/C27H48/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h19-25H,6-18H2,1-5H3/t20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
Download
View in JSmol
Synonyms
ValueSource
(5beta)-CholestaneChEBI
beta-CholestaneChEBI
CoprostaneChEBI
PseudocholestaneChEBI
(5b)-CholestaneGenerator
(5Β)-cholestaneGenerator
b-CholestaneGenerator
Β-cholestaneGenerator
5b-CholestaneGenerator
5Β-cholestaneGenerator
Chemical FormulaC27H48
Average Mass372.6700 Da
Monoisotopic Mass372.37560 Da
IUPAC Name(1S,2S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane
Traditional Name5β-cholestane
CAS Registry Number481-20-9
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CCCC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C27H48/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h19-25H,6-18H2,1-5H3/t20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyXIIAYQZJNBULGD-CJPSHIORSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Oryza sativaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholestane steroids. These are steroids with a structure containing the 27-carbon cholestane skeleton.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassCholestane steroids  
Direct ParentCholestane steroids  
Alternative Parents
Substituents
  • Cholestane-skeleton
    • 

  • Polycyclic hydrocarbon
    • 

  • Saturated hydrocarbon
    • 

  • Hydrocarbon
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.66ALOGPS
logP8.91ChemAxon
logS-7.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity118.1 m³·mol⁻¹ChemAxon
Polarizability49.92 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021856  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCoprostane  
METLIN IDNot Available
PubChem Compound5283630  
PDB IDNot Available
ChEBI ID35517  
Good Scents IDNot Available
References
General ReferencesNot Available