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

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Record Information

Version

2.0

Created at

2024-09-09 22:03:58 UTC

Updated at

2024-09-09 22:03:59 UTC

NP-MRD ID

NP0334073

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7a-Hydroxy-3-oxo-5b-cholanoic acid

Description

Glycine- 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

MOL SDF PDB SMILES InChI


  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


  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

$$$$

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

View in JSmol

Synonyms

Value	Source
7a-Hydroxy-3-oxo-5b-cholanoate	Generator

Chemical Formula

C₂₄H₃₈O₄

Average Mass

390.5640 Da

Monoisotopic Mass

390.27701 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 Number

Not 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 Key

KNVADAPHVNKTEP-PTBOWRHZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Vitamin D and derivatives

Direct Parent

Vitamin D and derivatives

Alternative Parents

Substituents

Polycyclic triterpenoid
Triterpenoid
Monohydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
3-oxo-5-beta-steroid
7-hydroxysteroid
7-alpha-hydroxysteroid
Oxosteroid
Hydroxysteroid
3-oxosteroid
Fatty acid
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.92	ChemAxon
pKa (Strongest Acidic)	4.6	ChemAxon
pKa (Strongest Basic)	-0.58	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.25 m³·mol⁻¹	ChemAxon
Polarizability	45.32 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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

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

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

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

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

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

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

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

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

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

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