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Showing NP-Card for 4b-Hydroxycholesterol (NP0339378)

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Record Information
Version2.0
Created at2024-09-11 21:32:16 UTC
Updated at2024-09-11 21:32:16 UTC
NP-MRD IDNP0339378
Secondary Accession NumbersNone
Natural Product Identification
Common Name4b-Hydroxycholesterol
Description4B-Hydroxycholesterol, also known as cholest-5-en-3b,4b-diol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 4b-hydroxycholesterol is considered to be a sterol lipid molecule. 4B-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339378 (4b-Hydroxycholesterol)


  Mrv0541 02271200292D          

 33 36  0  0  1  0            999 V2000
    9.0246   -6.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0246   -7.1238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7390   -7.5363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4535   -7.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4535   -6.2988    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7390   -5.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1679   -7.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8824   -7.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8824   -6.2988    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1679   -5.8863    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5969   -5.8863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5969   -5.0613    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8824   -4.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1679   -5.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3815   -6.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8665   -5.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3815   -4.8063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3101   -7.5363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6832   -4.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6365   -4.0217    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1679   -6.7113    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4535   -5.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8824   -5.4738    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6832   -6.7068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4434   -3.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6983   -3.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5053   -2.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1442   -4.6269    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0844   -3.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0573   -3.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8024   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8643   -3.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7390   -8.3613    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
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  2  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  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  1  0  0  0
 12 19  1  1  0  0  0
 17 20  1  0  0  0  0
 10 21  1  6  0  0  0
  5 22  1  1  0  0  0
  9 23  1  1  0  0  0
 11 24  1  6  0  0  0
 25 20  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 17 28  1  6  0  0  0
 20 29  1  6  0  0  0
 30 27  1  0  0  0  0
 31 30  1  0  0  0  0
 32 30  1  0  0  0  0
  3 33  1  1  0  0  0
M  END
Download

3D MOL for NP0339378 (4b-Hydroxycholesterol)

Download
3D SDF for NP0339378 (4b-Hydroxycholesterol)

  Mrv0541 02271200292D          

 33 36  0  0  1  0            999 V2000
    9.0246   -6.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0246   -7.1238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7390   -7.5363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4535   -7.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4535   -6.2988    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7390   -5.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1679   -7.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8824   -7.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8824   -6.2988    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1679   -5.8863    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5969   -5.8863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5969   -5.0613    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8824   -4.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1679   -5.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3815   -6.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8665   -5.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3815   -4.8063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3101   -7.5363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6832   -4.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6365   -4.0217    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1679   -6.7113    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4535   -5.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8824   -5.4738    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6832   -6.7068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4434   -3.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6983   -3.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5053   -2.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1442   -4.6269    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0844   -3.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0573   -3.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8024   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8643   -3.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7390   -8.3613    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
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  2  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  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  1  0  0  0
 12 19  1  1  0  0  0
 17 20  1  0  0  0  0
 10 21  1  6  0  0  0
  5 22  1  1  0  0  0
  9 23  1  1  0  0  0
 11 24  1  6  0  0  0
 25 20  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 17 28  1  6  0  0  0
 20 29  1  6  0  0  0
 30 27  1  0  0  0  0
 31 30  1  0  0  0  0
 32 30  1  0  0  0  0
  3 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0339378

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4[C@@H](O)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(29)24(28)14-16-27(23,5)22(19)13-15-26(20,21)4/h10,17-22,24-25,28-29H,6-9,11-16H2,1-5H3/t18-,19+,20-,21+,22+,24+,25-,26-,27-/m1/s1

> <INCHI_KEY>
CZDKQKOAHAICSF-JSAMMMMSSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.6529

> <EXACT_MASS>
402.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
51.39428933671995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,6R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,6-diol

> <ALOGPS_LOGP>
6.16

> <JCHEM_LOGP>
6.193892883666665

> <ALOGPS_LOGS>
-6.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.09152849411048

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.500174362553981

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1747438366026017

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
121.82399999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.74e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4β-hydroxy-cholesterol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339378 (4b-Hydroxycholesterol)
Download
PDB for NP0339378 (4b-Hydroxycholesterol)
HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      16.846 -11.758   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.846 -13.298   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.179 -14.068   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.513 -13.298   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.513 -11.758   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.179 -10.988   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.847 -14.068   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.180 -13.298   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.180 -11.758   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.847 -10.988   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.514 -10.988   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.514  -9.448   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.180  -8.678   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.847  -9.448   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.979 -11.464   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.884 -10.218   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.979  -8.972   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      15.512 -14.068   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      23.675  -7.916   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.455  -7.507   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      20.847 -12.528   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      19.513 -10.218   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      22.180 -10.218   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      23.675 -12.519   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0      26.961  -7.187   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      27.437  -5.722   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      28.943  -5.402   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      26.403  -8.637   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0      24.424  -6.363   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      29.974  -6.547   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      29.498  -8.011   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      31.480  -6.226   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      18.179 -15.608   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4   33                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   22                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   23                                             
CONECT   10    9    5   14   21                                             
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   20   28                                             
CONECT   18    2                                                            
CONECT   19   12                                                            
CONECT   20   17   25   29                                                  
CONECT   21   10                                                            
CONECT   22    5                                                            
CONECT   23    9                                                            
CONECT   24   11                                                            
CONECT   25   20   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   30                                                       
CONECT   28   17                                                            
CONECT   29   20                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    3                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

Download
3D PDB for NP0339378 (4b-Hydroxycholesterol)
Download
SMILES for NP0339378 (4b-Hydroxycholesterol)
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4[C@@H](O)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
Download
INCHI for NP0339378 (4b-Hydroxycholesterol)
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(29)24(28)14-16-27(23,5)22(19)13-15-26(20,21)4/h10,17-22,24-25,28-29H,6-9,11-16H2,1-5H3/t18-,19+,20-,21+,22+,24+,25-,26-,27-/m1/s1
Download
View in JSmol
Synonyms
ValueSource
(3beta,4beta)-Cholest-5-ene-3,4-diolChEBI
Cholest-5-en-3beta,4beta-diolChEBI
(3b,4b)-Cholest-5-ene-3,4-diolGenerator
(3Β,4β)-cholest-5-ene-3,4-diolGenerator
Cholest-5-en-3b,4b-diolGenerator
Cholest-5-en-3β,4β-diolGenerator
(4b)-Cholest-5-ene-3b,4-diolHMDB
(4b)-4-HydroxycholesterolHMDB
(4b)-Cholest-5-ene-3beta,4-diolHMDB
4-HydroxycholesterolHMDB
4b-Cholest-5-ene-3b,4-diolHMDB
4beta-HydroxycholesterolHMDB
Cholest-5-en-3beta,4b-diolHMDB
Cholest-5-ene-3,4-diolHMDB
Cholest-5-ene-3b,4b-diolHMDB
(3beta,4alpha)-Isomer OF cholest-5-ene-3,4-diolHMDB
Cholest-5-ene-3beta,4beta-diolHMDB
4b-Hydroxy-cholesterolGenerator
4Β-hydroxy-cholesterolGenerator
Chemical FormulaC27H46O2
Average Mass402.6529 Da
Monoisotopic Mass402.34978 Da
IUPAC Name(1S,2R,5S,6R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,6-diol
Traditional Name4β-hydroxy-cholesterol
CAS Registry NumberNot Available
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4[C@@H](O)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(29)24(28)14-16-27(23,5)22(19)13-15-26(20,21)4/h10,17-22,24-25,28-29H,6-9,11-16H2,1-5H3/t18-,19+,20-,21+,22+,24+,25-,26-,27-/m1/s1
InChI KeyCZDKQKOAHAICSF-JSAMMMMSSA-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 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 ParentsNot Available
SubstituentsNot Available
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
logP6.16ALOGPS
logP6.19ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)13.5ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.82 m³·mol⁻¹ChemAxon
Polarizability51.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013643  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029614  
KNApSAcK IDNot Available
Chemspider ID2497521  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3247060  
PDB IDNot Available
ChEBI ID85778  
Good Scents IDNot Available
References
General References