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Showing NP-Card for 23-Dehydrocholesterol (NP0046736)

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Record Information
Version2.0
Created at2022-03-17 20:28:39 UTC
Updated at2022-03-17 20:28:39 UTC
NP-MRD IDNP0046736
Secondary Accession NumbersNone
Natural Product Identification
Common Name23-Dehydrocholesterol
Description23-Dehydrocholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. 23-Dehydrocholesterol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046736 (23-Dehydrocholesterol)


  Mrv0541 02241212322D          

 28 31  0  0  0  0            999 V2000
   -3.3111   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0256   -1.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0256   -2.4239    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3111   -2.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5967   -2.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5967   -1.5989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8822   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8822   -2.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1677   -2.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1677   -1.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1677    0.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8822   -0.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2612    0.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533   -0.3614    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4533   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756   -0.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7401   -2.8364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5967   -0.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533    0.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9757    1.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2612    0.8761    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6901    0.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4046    1.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191    0.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8335    1.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191    0.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533    1.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  1  1  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  2  0  0  0  0
  7  6  1  0  0  0  0
  6 19  1  1  0  0  0
 12  7  1  0  0  0  0
  7 10  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
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 22 13  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 28  1  6  0  0  0
 23 24  2  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
M  END
Download

3D MOL for NP0046736 (23-Dehydrocholesterol)

Download
3D SDF for NP0046736 (23-Dehydrocholesterol)

  Mrv0541 02241212322D          

 28 31  0  0  0  0            999 V2000
   -3.3111   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0256   -1.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0256   -2.4239    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3111   -2.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5967   -2.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5967   -1.5989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8822   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8822   -2.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1677   -2.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1677   -1.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1677    0.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8822   -0.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2612    0.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533   -0.3614    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4533   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756   -1.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756   -0.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7401   -2.8364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5967   -0.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533    0.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9757    1.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2612    0.8761    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6901    0.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4046    1.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191    0.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8335    1.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191    0.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533    1.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  1  1  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  2  0  0  0  0
  7  6  1  0  0  0  0
  6 19  1  1  0  0  0
 12  7  1  0  0  0  0
  7 10  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
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 22 13  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 28  1  6  0  0  0
 23 24  2  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
M  END
> <DATABASE_ID>
NP0046736

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)\C=C\C[C@@H](C)C1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h6-7,9,18-19,21-25,28H,8,10-17H2,1-5H3/b7-6+/t19-,21+,22?,23?,24?,25?,26+,27-/m1/s1

> <INCHI_KEY>
QWRSWWMDQCPOTC-IUYVAJSCSA-N

> <FORMULA>
C27H44O

> <MOLECULAR_WEIGHT>
384.6377

> <EXACT_MASS>
384.33921603

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
49.375176134684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5S,15R)-2,15-dimethyl-14-[(2R,4E)-6-methylhept-4-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

> <ALOGPS_LOGP>
6.85

> <JCHEM_LOGP>
6.750967374

> <ALOGPS_LOGS>
-6.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <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>
121.73309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.46e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5S,15R)-2,15-dimethyl-14-[(2R,4E)-6-methylhept-4-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0046736 (23-Dehydrocholesterol)
Download
PDB for NP0046736 (23-Dehydrocholesterol)
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      -6.181  -2.215   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.514  -2.985   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.514  -4.525   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.181  -5.295   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.847  -4.525   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.847  -2.985   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.513  -2.215   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.513  -5.295   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.180  -4.525   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.180  -2.985   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.180   0.095   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.513  -0.675   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.488   0.095   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.846  -0.675   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.846  -2.215   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.821  -2.215   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.821  -0.675   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -8.848  -5.295   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.847  -1.445   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.846   0.865   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.821   2.405   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.488   1.635   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.155   1.635   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.489   2.405   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.822   1.635   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.156   2.405   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.822   0.095   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.846   2.405   0.000  0.00  0.00           C+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    5    7   19                                             
CONECT    7    6   12   10                                                  
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    7    9   15                                                  
CONECT   11   12   14                                                       
CONECT   12    7   11                                                       
CONECT   13   14   22   17                                                  
CONECT   14   11   13   15   20                                             
CONECT   15   10   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   13   16                                                       
CONECT   18    3                                                            
CONECT   19    6                                                            
CONECT   20   14                                                            
CONECT   21   22   23                                                       
CONECT   22   13   21   28                                                  
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

Download
3D PDB for NP0046736 (23-Dehydrocholesterol)
Download
SMILES for NP0046736 (23-Dehydrocholesterol)
CC(C)\C=C\C[C@@H](C)C1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
Download
INCHI for NP0046736 (23-Dehydrocholesterol)
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h6-7,9,18-19,21-25,28H,8,10-17H2,1-5H3/b7-6+/t19-,21+,22?,23?,24?,25?,26+,27-/m1/s1
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC27H44O
Average Mass384.6377 Da
Monoisotopic Mass384.33922 Da
IUPAC Name(2R,5S,15R)-2,15-dimethyl-14-[(2R,4E)-6-methylhept-4-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
Traditional Name(2R,5S,15R)-2,15-dimethyl-14-[(2R,4E)-6-methylhept-4-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
CAS Registry NumberNot Available
SMILES
CC(C)\C=C\C[C@@H](C)C1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h6-7,9,18-19,21-25,28H,8,10-17H2,1-5H3/b7-6+/t19-,21+,22?,23?,24?,25?,26+,27-/m1/s1
InChI KeyQWRSWWMDQCPOTC-IUYVAJSCSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Helianthus annuus L.FooDB
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassCholestane steroids  
Direct ParentCholesterols and derivatives  
Alternative Parents
Substituents
  • Cholesterol-skeleton
    • 

  • Cholesterol
    • 

  • 3-beta-hydroxysteroid
    • 

  • 3-beta-hydroxy-delta-5-steroid
    • 

  • 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
logP6.85ALOGPS
logP6.75ChemAxon
logS-6.9ALOGPS
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 Count4ChemAxon
Refractivity121.73 m³·mol⁻¹ChemAxon
Polarizability49.38 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 IDFDB005686  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available