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Showing NP-Card for alpha-Sitosterol (NP0336530)

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Record Information
Version2.0
Created at2024-09-11 06:43:35 UTC
Updated at2024-09-11 06:43:35 UTC
NP-MRD IDNP0336530
Secondary Accession NumbersNone
Natural Product Identification
Common Namealpha-Sitosterol
DescriptionAlpha-Sitosterol, also known as α-sitosterol, belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Alpha-Sitosterol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336530 (alpha-Sitosterol)


  Mrv0541 02241212592D          

 31 34  0  0  1  0            999 V2000
   -0.7079    1.4619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0065    1.8744    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7210    1.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4355    1.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1500    1.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    1.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    2.6994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1500    3.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1500    3.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    4.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5789    3.9369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5789    3.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3635    2.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8484    3.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3635    4.1919    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6185    4.9765    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6651    4.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4355    2.6994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4355    3.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7210    3.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0065    2.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0664    5.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4254    5.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9775    4.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7844    4.7065    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3365    4.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    3.5244    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0394    5.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8463    5.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1434    4.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0815    3.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  0  0  0  0
  7  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  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  1  0  0  0
 11 17  1  1  0  0  0
  8 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
 16 22  1  6  0  0  0
 16 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
  7 27  1  1  0  0  0
 25 28  1  1  0  0  0
 28 29  1  0  0  0  0
 26 30  1  0  0  0  0
 26 31  1  0  0  0  0
M  END
Download

3D MOL for NP0336530 (alpha-Sitosterol)

Download
3D SDF for NP0336530 (alpha-Sitosterol)

  Mrv0541 02241212592D          

 31 34  0  0  1  0            999 V2000
   -0.7079    1.4619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0065    1.8744    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7210    1.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4355    1.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1500    1.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    1.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    2.6994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1500    3.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1500    3.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    4.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5789    3.9369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5789    3.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3635    2.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8484    3.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3635    4.1919    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6185    4.9765    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6651    4.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4355    2.6994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4355    3.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7210    3.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0065    2.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0664    5.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4254    5.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9775    4.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7844    4.7065    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3365    4.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    3.5244    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0394    5.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8463    5.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1434    4.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0815    3.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  0  0  0  0
  7  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  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  1  0  0  0
 11 17  1  1  0  0  0
  8 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
 16 22  1  6  0  0  0
 16 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
  7 27  1  1  0  0  0
 25 28  1  1  0  0  0
 28 29  1  0  0  0  0
 26 30  1  0  0  0  0
 26 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336530

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC=C3C[C@H](O)CC[C@]3(C)C1CC[C@]1(C)[C@H](CCC21)[C@H](C)CC[C@@H](CC)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23-,24+,25-,26?,27?,28+,29-/m1/s1

> <INCHI_KEY>
KZJWDPNRJALLNS-GGRCZSEBSA-N

> <FORMULA>
C29H50O

> <MOLECULAR_WEIGHT>
414.7067

> <EXACT_MASS>
414.386166222

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
52.75485048932029

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5R,10S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

> <ALOGPS_LOGP>
7.27

> <JCHEM_LOGP>
7.844476792000004

> <ALOGPS_LOGS>
-7.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972437702926293

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
129.7661

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.84e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5R,10S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0336530 (alpha-Sitosterol)
Download
PDB for NP0336530 (alpha-Sitosterol)
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  O   UNK     0      -1.321   2.729   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.012   3.499   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.346   2.729   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.680   3.499   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.013   2.729   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.347   3.499   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.347   5.039   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.013   5.809   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.013   7.349   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.347   8.119   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.681   7.349   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.681   5.809   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.145   5.333   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.050   6.579   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.145   7.825   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.621   9.289   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.842   8.880   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.680   5.039   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.680   6.579   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.346   5.809   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.012   5.039   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.591  10.434   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.127   9.610   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.158   8.465   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.664   8.785   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.695   7.641   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       5.347   6.579   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0      13.140  10.250   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.646  10.570   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.201   7.961   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.219   6.176   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12   27                                             
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15   17                                             
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11   16                                                  
CONECT   16   15   22   23                                                  
CONECT   17   11                                                            
CONECT   18    8    4   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20    2                                                       
CONECT   22   16                                                            
CONECT   23   16   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   30   31                                                  
CONECT   27    7                                                            
CONECT   28   25   29                                                       
CONECT   29   28                                                            
CONECT   30   26                                                            
CONECT   31   26                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

Download
3D PDB for NP0336530 (alpha-Sitosterol)
Download
SMILES for NP0336530 (alpha-Sitosterol)
[H][C@@]12CC=C3C[C@H](O)CC[C@]3(C)C1CC[C@]1(C)[C@H](CCC21)[C@H](C)CC[C@@H](CC)C(C)C
Download
INCHI for NP0336530 (alpha-Sitosterol)
InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23-,24+,25-,26?,27?,28+,29-/m1/s1
Download
View in JSmol
Synonyms
ValueSource
a-SitosterolGenerator
Α-sitosterolGenerator
Chemical FormulaC29H50O
Average Mass414.7067 Da
Monoisotopic Mass414.38617 Da
IUPAC Name(2R,5R,10S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
Traditional Name(2R,5R,10S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC=C3C[C@H](O)CC[C@]3(C)C1CC[C@]1(C)[C@H](CCC21)[C@H](C)CC[C@@H](CC)C(C)C
InChI Identifier
InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23-,24+,25-,26?,27?,28+,29-/m1/s1
InChI KeyKZJWDPNRJALLNS-GGRCZSEBSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassStigmastanes and derivatives  
Direct ParentStigmastanes and derivatives  
Alternative Parents
Substituents
  • Triterpenoid
    • 

  • Stigmastane-skeleton
    • 

  • C24-propyl-sterol-skeleton
    • 

  • 3-alpha-hydroxysteroid
    • 

  • Hydroxysteroid
    • 

  • 3-hydroxysteroid
    • 

  • 3-hydroxy-delta-5-steroid
    • 

  • Delta-5-steroid
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP7.27ALOGPS
logP7.84ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity129.77 m³·mol⁻¹ChemAxon
Polarizability52.75 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007299  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound135299228  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available