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Showing NP-Card for Sterols (NP0046224)

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Record Information
Version2.0
Created at2022-03-17 19:50:30 UTC
Updated at2022-03-17 19:50:30 UTC
NP-MRD IDNP0046224
Secondary Accession NumbersNone
Natural Product Identification
Common NameSterols
DescriptionSterol belongs to the class of organic compounds known as 3-hydroxysteroids. These are steroids carrying a hydroxyl group at the 3-position of the steroid backbone. Sterol is an extremely weak basic (essentially neutral) compound (based on its pKa). Sterol exists in all living organisms, ranging from bacteria to humans. Sterols and related compounds play essential roles in the physiology of eukaryotic organisms. In humans, sterol is involved in the metabolic disorder called the child syndrome pathway. Outside of the human body, Sterol is found, on average, in the highest concentration within sesames and burdocks. Sterol has also been detected, but not quantified in, soft-necked garlics. This could make sterol a potential biomarker for the consumption of these foods. Preliminary research has shown that phytosterols may have anticancer effects. The most important zoosterol is cholesterol; notable phytosterols include campesterol, sitosterol, and stigmasterol. The most familiar type of animal sterol is cholesterol, which is vital to cell membrane structure, and functions as a precursor to fat-soluble vitamins and steroid hormones. They are amphipathic lipids synthesized from acetyl-coenzyme A via the HMG-CoA reductase pathway. They are currently approved by the U.S. Sterols was first documented in 2010 (PMID: 20044567). Food and Drug Administration for use as a food supplement; however, there is some concern that they may block absorption not only of cholesterol, but of other important nutrients as well.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0046224 (Sterols)

 
  Mrv0541 02241221412D          

 18 21  0  0  0  0            999 V2000
   -3.0643    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7788    1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7788    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0643   -0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3498    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3498    1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6354    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6354   -0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9209    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9209    1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9209    2.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6354    2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5080    2.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064    2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2225    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2225    2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4932   -0.2357    0.0000 O   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
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
  7 10  1  0  0  0  0
 12  7  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
  3 18  1  0  0  0  0
M  END
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3D MOL for NP0046224 (Sterols)

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3D SDF for NP0046224 (Sterols)
 
  Mrv0541 02241221412D          

 18 21  0  0  0  0            999 V2000
   -3.0643    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7788    1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7788    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0643   -0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3498    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3498    1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6354    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6354   -0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9209    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9209    1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9209    2.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6354    2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5080    2.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064    2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2225    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2225    2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4932   -0.2357    0.0000 O   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
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
  7 10  1  0  0  0  0
 12  7  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
  3 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046224

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CCC2C(CCC3C4CCCC4CCC23)C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H28O/c18-13-6-9-15-12(10-13)5-8-16-14-3-1-2-11(14)4-7-17(15)16/h11-18H,1-10H2

> <INCHI_KEY>
FPXSXMFOYWRHDX-UHFFFAOYSA-N

> <FORMULA>
C17H28O

> <MOLECULAR_WEIGHT>
248.4036

> <EXACT_MASS>
248.214015518

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
31.23893132452884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol

> <ALOGPS_LOGP>
4.57

> <JCHEM_LOGP>
3.8344736580000003

> <ALOGPS_LOGS>
-5.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.30946884965182

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3512383251622921

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
74.16550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.93e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sterol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0046224 (Sterols)
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PDB for NP0046224 (Sterols)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.720   2.640   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.054   1.870   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.054   0.330   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.720  -0.440   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.386   0.330   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.386   1.870   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.053   2.640   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.053  -0.440   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.719   0.330   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.719   1.870   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.719   4.950   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.053   4.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.948   4.950   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.385   4.180   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.385   2.640   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.282   2.640   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.282   4.180   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -8.387  -0.440   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10   12                                                  
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   15    7                                                  
CONECT   11   12   14                                                       
CONECT   12    7   11                                                       
CONECT   13   14   17                                                       
CONECT   14   11   13   15                                                  
CONECT   15   10   16   14                                                  
CONECT   16   17   15                                                       
CONECT   17   16   13                                                       
CONECT   18    3                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

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3D PDB for NP0046224 (Sterols)
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SMILES for NP0046224 (Sterols)
OC1CCC2C(CCC3C4CCCC4CCC23)C1
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INCHI for NP0046224 (Sterols)
InChI=1S/C17H28O/c18-13-6-9-15-12(10-13)5-8-16-14-3-1-2-11(14)4-7-17(15)16/h11-18H,1-10H2
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SynonymsNot Available
Chemical FormulaC17H28O
Average Mass248.4036 Da
Monoisotopic Mass248.21402 Da
IUPAC Nametetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol
Traditional Namesterol
CAS Registry Number68555-08-8
SMILES
OC1CCC2C(CCC3C4CCCC4CCC23)C1
InChI Identifier
InChI=1S/C17H28O/c18-13-6-9-15-12(10-13)5-8-16-14-3-1-2-11(14)4-7-17(15)16/h11-18H,1-10H2
InChI KeyFPXSXMFOYWRHDX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium sativumFooDB
Arctium lappaFooDB
Sesamum indicumFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-hydroxysteroids. These are steroids carrying a hydroxyl group at the 3-position of the steroid backbone.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassHydroxysteroids  
Direct Parent3-hydroxysteroids  
Alternative Parents
Substituents
  • 3-hydroxysteroid
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • 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
logP4.57ALOGPS
logP3.83ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)18.31ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity74.17 m³·mol⁻¹ChemAxon
Polarizability31.24 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0060512  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003714  
KNApSAcK IDNot Available
Chemspider ID1076  
KEGG Compound IDC00370  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSterol  
METLIN IDNot Available
PubChem Compound1107  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567  ]