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Showing NP-Card for 7a-Hydroxy-3-oxo-5b-cholanoic acid (NP0334073)

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Record Information
Version2.0
Created at2024-09-09 22:03:58 UTC
Updated at2024-09-09 22:03:59 UTC
NP-MRD IDNP0334073
Secondary Accession NumbersNone
Natural Product Identification
Common Name7a-Hydroxy-3-oxo-5b-cholanoic acid
DescriptionGlycine- and taurine-conjugated 7 alpha-hydroxy-3-oxo-5 beta-cholanoic acid has been identified in normal human serum (PMID 1939467 ) and as a cholesterol metabolite in bile acids produced in HepG2 cells -a well-differentiated human hepatoblastoma cell line. (PMID 1655725 ) [HMDB]
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334073 (7a-Hydroxy-3-oxo-5b-cholanoic acid)


  Mrv2104 05252300362D          

 35 38  0  0  1  0            999 V2000
    2.0850   -0.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611    0.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7451    0.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9568    0.5575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0511    1.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7340    2.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4505   -0.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8853    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4489    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0732    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6368    0.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6338    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2898    2.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7741    0.4446    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8217    2.2807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1656    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2804    1.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3853    1.8451    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7292    1.3596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4777    2.7662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3668    0.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974    1.9903    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5414    1.5048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1050    1.0691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9777    1.9404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9459    3.3969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8731   -0.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6776    0.7832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677   -0.2067    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1020    3.0566    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4702    1.2514    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9171    1.2144    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0095    2.1355    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580    3.5421    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6656    2.6210    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 14  1  1  0  0  0  0
 23  2  1  6  0  0  0
 24  3  1  6  0  0  0
  4  7  1  0  0  0  0
 14  4  1  0  0  0  0
  5  6  1  0  0  0  0
  5 17  1  0  0  0  0
 18  6  1  0  0  0  0
  7 21  1  0  0  0  0
  8 10  1  0  0  0  0
  8 16  1  0  0  0  0
  9 11  1  0  0  0  0
 19  9  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  1  0  0  0  0
 15 12  1  0  0  0  0
 12 16  1  0  0  0  0
 15 13  1  0  0  0  0
 20 13  1  0  0  0  0
 14 29  1  1  0  0  0
 14 17  1  0  0  0  0
 15 30  1  1  0  0  0
 23 15  1  0  0  0  0
 16 25  2  0  0  0  0
 17 31  1  0  0  0  0
 24 17  1  0  0  0  0
 18 32  1  6  0  0  0
 22 18  1  0  0  0  0
 18 24  1  0  0  0  0
 19 33  1  6  0  0  0
 22 19  1  0  0  0  0
 19 23  1  0  0  0  0
 20 34  1  1  0  0  0
 22 20  1  0  0  0  0
 20 26  1  0  0  0  0
 21 27  2  0  0  0  0
 21 28  1  0  0  0  0
 22 35  1  1  0  0  0
M  END
Download

3D MOL for NP0334073 (7a-Hydroxy-3-oxo-5b-cholanoic acid)

Download
3D SDF for NP0334073 (7a-Hydroxy-3-oxo-5b-cholanoic acid)

  Mrv2104 05252300362D          

 35 38  0  0  1  0            999 V2000
    2.0850   -0.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611    0.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7451    0.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9568    0.5575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0511    1.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7340    2.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4505   -0.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8853    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4489    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0732    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6368    0.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6338    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2898    2.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7741    0.4446    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8217    2.2807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1656    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2804    1.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3853    1.8451    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7292    1.3596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4777    2.7662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3668    0.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974    1.9903    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5414    1.5048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1050    1.0691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9777    1.9404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9459    3.3969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8731   -0.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6776    0.7832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677   -0.2067    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1020    3.0566    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4702    1.2514    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9171    1.2144    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0095    2.1355    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580    3.5421    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6656    2.6210    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 14  1  1  0  0  0  0
 23  2  1  6  0  0  0
 24  3  1  6  0  0  0
  4  7  1  0  0  0  0
 14  4  1  0  0  0  0
  5  6  1  0  0  0  0
  5 17  1  0  0  0  0
 18  6  1  0  0  0  0
  7 21  1  0  0  0  0
  8 10  1  0  0  0  0
  8 16  1  0  0  0  0
  9 11  1  0  0  0  0
 19  9  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  1  0  0  0  0
 15 12  1  0  0  0  0
 12 16  1  0  0  0  0
 15 13  1  0  0  0  0
 20 13  1  0  0  0  0
 14 29  1  1  0  0  0
 14 17  1  0  0  0  0
 15 30  1  1  0  0  0
 23 15  1  0  0  0  0
 16 25  2  0  0  0  0
 17 31  1  0  0  0  0
 24 17  1  0  0  0  0
 18 32  1  6  0  0  0
 22 18  1  0  0  0  0
 18 24  1  0  0  0  0
 19 33  1  6  0  0  0
 22 19  1  0  0  0  0
 19 23  1  0  0  0  0
 20 34  1  1  0  0  0
 22 20  1  0  0  0  0
 20 26  1  0  0  0  0
 21 27  2  0  0  0  0
 21 28  1  0  0  0  0
 22 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0334073

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](C)(CCC(O)=O)C1([H])CC[C@@]2([H])[C@]3([H])[C@]([H])(O)C[C@]4([H])CC(=O)CC[C@@]4(C)[C@@]3([H])CC[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-15,17-20,22,26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,17?,18+,19+,20-,22+,23-,24+/m1/s1

> <INCHI_KEY>
KNVADAPHVNKTEP-PTBOWRHZSA-N

> <FORMULA>
C24H38O4

> <MOLECULAR_WEIGHT>
390.564

> <EXACT_MASS>
390.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
45.320780699484864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(3aS,3bR,4R,5aR,9aR,9bS,11aS)-4-hydroxy-9a,11a-dimethyl-7-oxo-hexadecahydrocyclopenta[a]phenanthren-1-yl]pentanoic acid

> <JCHEM_LOGP>
3.920806325333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.595945445459593

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5821739475897946

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
108.24569999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(3aS,3bR,4R,5aR,9aR,9bS,11aS)-4-hydroxy-9a,11a-dimethyl-7-oxo-tetradecahydrocyclopenta[a]phenanthren-1-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0334073 (7a-Hydroxy-3-oxo-5b-cholanoic acid)
Download
PDB for NP0334073 (7a-Hydroxy-3-oxo-5b-cholanoic acid)
HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0       3.892  -0.597   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.821   1.361   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.124   0.610   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.786   1.041   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.829   3.525   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.103   4.389   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.841  -0.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.853   1.903   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.305   1.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.337   1.632   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.789   0.818   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.383   4.528   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.874   5.435   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.312   0.830   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.867   4.257   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.376   3.351   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.257   2.046   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.319   3.444   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.828   2.538   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.358   5.164   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.685   0.035   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.835   3.715   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.344   2.809   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.796   1.996   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.892   3.622   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.366   6.341   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.630  -1.180   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.265   1.462   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0       2.366  -0.386   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      11.390   5.706   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.744   2.336   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       7.312   2.267   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       9.351   3.986   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       8.882   6.612   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       6.842   4.893   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4    7   14                                                       
CONECT    5    6   17                                                       
CONECT    6    5   18                                                       
CONECT    7    4   21                                                       
CONECT    8   10   16                                                       
CONECT    9   11   19                                                       
CONECT   10    8   23                                                       
CONECT   11    9   24                                                       
CONECT   12   15   16                                                       
CONECT   13   15   20                                                       
CONECT   14    1    4   29   17                                             
CONECT   15   12   13   30   23                                             
CONECT   16    8   12   25                                                  
CONECT   17    5   14   31   24                                             
CONECT   18    6   32   22   24                                             
CONECT   19    9   33   22   23                                             
CONECT   20   13   34   22   26                                             
CONECT   21    7   27   28                                                  
CONECT   22   18   19   20   35                                             
CONECT   23    2   10   15   19                                             
CONECT   24    3   11   17   18                                             
CONECT   25   16                                                            
CONECT   26   20                                                            
CONECT   27   21                                                            
CONECT   28   21                                                            
CONECT   29   14                                                            
CONECT   30   15                                                            
CONECT   31   17                                                            
CONECT   32   18                                                            
CONECT   33   19                                                            
CONECT   34   20                                                            
CONECT   35   22                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

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3D PDB for NP0334073 (7a-Hydroxy-3-oxo-5b-cholanoic acid)
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SMILES for NP0334073 (7a-Hydroxy-3-oxo-5b-cholanoic acid)
[H][C@@](C)(CCC(O)=O)C1([H])CC[C@@]2([H])[C@]3([H])[C@]([H])(O)C[C@]4([H])CC(=O)CC[C@@]4(C)[C@@]3([H])CC[C@@]12C
Download
INCHI for NP0334073 (7a-Hydroxy-3-oxo-5b-cholanoic acid)
InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-15,17-20,22,26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,17?,18+,19+,20-,22+,23-,24+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC24H38O4
Average Mass390.5640 Da
Monoisotopic Mass390.27701 Da
IUPAC Name(4R)-4-[(3aS,3bR,4R,5aR,9aR,9bS,11aS)-4-hydroxy-9a,11a-dimethyl-7-oxo-hexadecahydrocyclopenta[a]phenanthren-1-yl]pentanoic acid
Traditional Name(4R)-4-[(3aS,3bR,4R,5aR,9aR,9bS,11aS)-4-hydroxy-9a,11a-dimethyl-7-oxo-tetradecahydrocyclopenta[a]phenanthren-1-yl]pentanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](C)(CCC(O)=O)C1([H])CC[C@@]2([H])[C@]3([H])[C@]([H])(O)C[C@]4([H])CC(=O)CC[C@@]4(C)[C@@]3([H])CC[C@@]12C
InChI Identifier
InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-15,17-20,22,26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,17?,18+,19+,20-,22+,23-,24+/m1/s1
InChI KeyKNVADAPHVNKTEP-PTBOWRHZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
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
logP3.92ChemAxon
pKa (Strongest Acidic)4.6ChemAxon
pKa (Strongest Basic)-0.58ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity108.25 m³·mol⁻¹ChemAxon
Polarizability45.32 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External LinksNot Available
References
General References
  1. Goto J, Saisho Y, Nambara T: Studies on steroids. CCLII. Separation and characterization of 3-oxobile acids in serum by high-performance liquid chromatography with fluorescence detection. J Chromatogr. 1991 Jul 5;567(2):343-9. [PubMed:1939467  ] 
  2. Axelson M, Mork B, Everson GT: Bile acid synthesis in cultured human hepatoblastoma cells. J Biol Chem. 1991 Sep 25;266(27):17770-7. [PubMed:1655725  ]