NP-MRD: Showing NP-Card for 5alpha-Cholestane (NP0049945)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 21:20:39 UTC

Updated at

2022-03-17 21:20:39 UTC

NP-MRD ID

NP0049945

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5alpha-Cholestane

Description

5Alpha-Cholestane, also known as α-cholestane, belongs to the class of organic compounds known as cholestane steroids. These are steroids with a structure containing the 27-carbon cholestane skeleton. The 5alpha-stereoisomer of cholestane. 5Alpha-Cholestane is possibly neutral. Outside of the human body, 5alpha-cholestane has been detected, but not quantified in, potato. This could make 5alpha-cholestane a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222492D          

 32 35  0  0  0  0            999 V2000
   -5.3036   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0180   -2.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0180   -3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3036   -4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5891   -3.7714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5891   -2.9464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8746   -2.5339    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8746   -4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1602   -3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1602   -2.9464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1602   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8746   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313   -1.2964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4457   -1.7089    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4457   -2.5339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0168   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0168   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5891   -2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313   -0.4714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0168   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3023   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1266   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8411   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1266   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5891   -4.5964    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1602   -2.1214    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8746   -3.3589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457   -3.3589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9344   -1.0829    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
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 15  1  0  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 15 16  1  0  0  0  0
 14 15  1  0  0  0  0
  6 18  1  1  0  0  0
 14 19  1  1  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  5 28  1  6  0  0  0
 10 29  1  1  0  0  0
  7 30  1  6  0  0  0
 15 31  1  6  0  0  0
 13 32  1  6  0  0  0
M  END


  Mrv0541 02241222492D          

 32 35  0  0  0  0            999 V2000
   -5.3036   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0180   -2.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0180   -3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3036   -4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5891   -3.7714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5891   -2.9464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8746   -2.5339    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8746   -4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1602   -3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1602   -2.9464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1602   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8746   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313   -1.2964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4457   -1.7089    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4457   -2.5339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0168   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0168   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5891   -2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313   -0.4714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0168   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3023   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1266   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8411   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1266   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5891   -4.5964    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1602   -2.1214    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8746   -3.3589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457   -3.3589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9344   -1.0829    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
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 15  1  0  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 15 16  1  0  0  0  0
 14 15  1  0  0  0  0
  6 18  1  1  0  0  0
 14 19  1  1  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  5 28  1  6  0  0  0
 10 29  1  1  0  0  0
  7 30  1  6  0  0  0
 15 31  1  6  0  0  0
 13 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0049945

> <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-XWLABEFZSA-N

> <FORMULA>
C27H48

> <MOLECULAR_WEIGHT>
372.67

> <EXACT_MASS>
372.375601536

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
50.24632188276611

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,7R,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>
118.09699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.61e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5α-cholestane

> <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      -9.900  -4.730   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.234  -5.500   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.234  -7.040   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.900  -7.810   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.566  -7.040   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.566  -5.500   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.233  -4.730   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.233  -7.810   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.899  -7.040   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.899  -5.500   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.899  -2.420   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.233  -3.190   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.232  -2.420   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.565  -3.190   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.565  -4.730   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.898  -4.730   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.898  -3.190   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.566  -3.960   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.565  -1.650   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.232  -0.880   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.898  -0.110   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.565  -0.110   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.564  -0.880   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.769  -0.110   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.103  -0.880   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.437  -0.110   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.103  -2.420   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      -8.566  -8.580   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      -5.899  -3.960   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      -7.233  -6.270   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.565  -6.270   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.744  -2.021   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8   28                                             
CONECT    6    1    7    5   18                                             
CONECT    7    6   10   12   30                                             
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   15    7   29                                             
CONECT   11   12   14                                                       
CONECT   12    7   11                                                       
CONECT   13   14   17   20   32                                             
CONECT   14   11   13   15   19                                             
CONECT   15   10   16   14   31                                             
CONECT   16   17   15                                                       
CONECT   17   16   13                                                       
CONECT   18    6                                                            
CONECT   19   14                                                            
CONECT   20   13   21   22                                                  
CONECT   21   20   23                                                       
CONECT   22   20                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28    5                                                            
CONECT   29   10                                                            
CONECT   30    7                                                            
CONECT   31   15                                                            
CONECT   32   13                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(5alpha)-Cholestane	ChEBI
alpha-Cholestane	ChEBI
(5a)-Cholestane	Generator
(5Α)-cholestane	Generator
a-Cholestane	Generator
Α-cholestane	Generator
5a-Cholestane	Generator
5Α-cholestane	Generator
28,29,30-Trinorlanostane	HMDB
5alpha-Cholestane (8ci)	HMDB
Cholestane	HMDB

Chemical Formula

C₂₇H₄₈

Average Mass

372.6700 Da

Monoisotopic Mass

372.37560 Da

IUPAC Name

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

Traditional Name

5α-cholestane

CAS Registry Number

481-21-0

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-XWLABEFZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholestane steroids

Alternative Parents

Substituents

Cholestane-skeleton
Polycyclic hydrocarbon
Saturated hydrocarbon
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cholestane (CHEBI:35515 )

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	7.66	ALOGPS
logP	8.91	ChemAxon
logS	-7.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	118.1 m³·mol⁻¹	ChemAxon
Polarizability	50.25 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

HMDB0041632

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021855

KNApSAcK ID

Not Available

Chemspider ID

2006076

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2723895

PDB ID

Not Available

ChEBI ID

35515

Good Scents ID

Not Available

References

General References

Showing NP-Card for 5alpha-Cholestane (NP0049945)

MOL for NP0049945 (5alpha-Cholestane)

3D MOL for NP0049945 (5alpha-Cholestane)

3D SDF for NP0049945 (5alpha-Cholestane)

3D-SDF for NP0049945 (5alpha-Cholestane)

PDB for NP0049945 (5alpha-Cholestane)

3D PDB for NP0049945 (5alpha-Cholestane)

SMILES for NP0049945 (5alpha-Cholestane)

INCHI for NP0049945 (5alpha-Cholestane)

Structure for NP0049945 (5alpha-Cholestane)

3D Structure for NP0049945 (5alpha-Cholestane)