NP-MRD: Showing NP-Card for 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid (NP0136233)

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Record Information

Version

2.0

Created at

2022-05-12 15:09:13 UTC

Updated at

2022-05-12 15:09:14 UTC

NP-MRD ID

NP0136233

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid

Description

7Alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid, also known as 3-dehydrochenodeoxycholic acid or (5b,7a)-7-hydroxy-3-oxocholan-24-Oate, belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid was first documented in 1985 (PMID: 2864922). 7Alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 18583509).

Structure

MOL 3D MOL SDF PDB SMILES InChI

      
  Mrv1652304062012582D          

 33 36  0  0  0  0            999 V2000
10000.340010001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9999.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3421 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0597 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9142 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6270 9999.7850    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.3400 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4883 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4883 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2001 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2001 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9147 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6292 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.627510000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.913010000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9130 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6275 9998.9658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.6116 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.342010000.2032    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3420 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1266 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.126610000.4581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.126610001.2832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.842310001.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.555910001.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.271610001.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.985110001.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.271610002.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.412910001.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.842310000.8707    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
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 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
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 21 24  1  0  0  0  0
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 23 24  1  0  0  0  0
 11  4  2  0  0  0  0
 16  3  1  6  0  0  0
  9 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14  5  1  1  0  0  0
 13  2  1  1  0  0  0
 19 13  1  0  0  0  0
 16 20  1  0  0  0  0
 19  6  1  6  0  0  0
 20  7  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
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 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 21 25  1  0  0  0  0
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 25 33  1  6  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23  8  1  6  0  0  0
 22  1  1  1  0  0  0
M  END

     RDKit          3D

 66 69  0  0  0  0  0  0  0  0999 V2000
    4.0707   -0.8678    0.9938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7108    0.2176    0.0223 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.7906    0.3003   -0.1002 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9766    1.4039    0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4411    1.4364    0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1381    0.1099    0.0776 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0790   -0.4624    1.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1131    0.0907    0.5800 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8546   -0.5616    1.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7446    1.4434    0.9270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2032    1.2556    1.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8555    0.8478   -0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9807    1.1586   -0.2627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0740    0.0600   -0.9865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9780   -0.7561   -0.2864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2896   -1.5303   -1.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8772   -1.8990   -1.1250 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2722   -1.8873   -2.4056 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1141   -1.2716    0.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0768   -0.5455    2.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4222   -1.7594    0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572    0.1011   -0.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2282    1.7659    1.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8896    2.3945   -0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3382    2.6612    1.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4473    0.9267    2.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5086    0.9427    0.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3639    0.8494   -1.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2313   -1.9413   -1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5544   -1.1266   -2.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1944   -2.6322   -0.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854   -2.5410   -1.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0966   -0.2166   -1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9412   -1.5559    0.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0171    0.6255   -1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448    2.3668    0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0781    1.4772    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9665    2.2321    0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259    1.7757   -1.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7730    0.0007    2.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640   -0.1924    1.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1015   -1.5703    1.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896   -1.6260    1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1729    0.0444    2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8127   -0.5745    2.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6737    2.1321    0.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2537    1.8276    1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4339    0.4765    1.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6330    2.1992    1.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5116    0.7745   -1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6498   -0.6179   -1.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5506   -1.4452    0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7921   -2.5850   -2.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
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  5  6  2  0
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 17 50  1  0
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  4 35  1  0
  4 36  1  0
  7 37  1  0
M  END

      
  Mrv1652304062012582D          

 33 36  0  0  0  0            999 V2000
10000.340010001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9999.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3421 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0597 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9142 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6270 9999.7850    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.3400 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4883 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4883 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2001 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2001 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9147 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6292 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.627510000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.913010000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9130 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6275 9998.9658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.6116 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.342010000.2032    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3420 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1266 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.126610000.4581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.126610001.2832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.842310001.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.555910001.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.271610001.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.985110001.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.271610002.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.412910001.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.842310000.8707    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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 29 31  2  0  0  0  0
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 22  1  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0136233

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(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)[C@H](C)CCC(O)=O

> <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-CIGXQKLNSA-N

> <FORMULA>
C24H38O4

> <MOLECULAR_WEIGHT>
390.564

> <EXACT_MASS>
390.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
45.49401187526238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
3.920806325333333

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.9878464561783

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.595945445459592

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5821739475897946

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
108.24569999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    8667.3018668.598   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.3108666.265   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8667.3058662.405   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8659.3118662.405   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8663.3108661.633   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8664.6408663.961   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8665.9708666.265   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0    8667.3018663.961   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0    8661.9788665.489   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8660.6448664.719   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8660.6448663.179   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.9788662.409   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8663.3078664.719   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.3078663.179   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.6418662.409   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.9758663.179   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.9718667.816   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8664.6388667.046   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.6388665.506   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8665.9718664.736   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.6758666.276   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8667.3058667.046   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.3058665.506   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.7708665.030   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.7708667.522   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8668.7708669.062   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8670.1068669.832   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8671.4388669.062   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8672.7748669.832   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0    8674.1068669.062   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0    8672.7748671.372   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0    8667.4378669.832   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0    8670.1068668.292   0.000  0.00  0.00           H+0
CONECT    1   22                                                            
CONECT    2   13                                                            
CONECT    3   16                                                            
CONECT    4   11                                                            
CONECT    5   14                                                            
CONECT    6   19                                                            
CONECT    7   20                                                            
CONECT    8   23                                                            
CONECT    9   10   13                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    4                                                  
CONECT   12   11   14                                                       
CONECT   13   14    9    2   19                                             
CONECT   14   13   15   12    5                                             
CONECT   15   14   16                                                       
CONECT   16   15    3   20                                                  
CONECT   17   18   22                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   13    6                                             
CONECT   20   19   16    7   23                                             
CONECT   21   24   25                                                       
CONECT   22   23   25   17    1                                             
CONECT   23   22   24   20    8                                             
CONECT   24   21   23                                                       
CONECT   25   26   21   22   33                                             
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   26                                                            
CONECT   33   25                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(5beta,7alpha)-7-Hydroxy-3-oxocholan-24-Oic acid	ChEBI
3-Dehydrochenodeoxycholic acid	ChEBI
3-Oxochenodeoxycholic acid	ChEBI
Dehydrochenodeoxycholic acid	ChEBI
(5b,7a)-7-Hydroxy-3-oxocholan-24-Oate	Generator
(5b,7a)-7-Hydroxy-3-oxocholan-24-Oic acid	Generator
(5beta,7alpha)-7-Hydroxy-3-oxocholan-24-Oate	Generator
(5Β,7α)-7-hydroxy-3-oxocholan-24-Oate	Generator
(5Β,7α)-7-hydroxy-3-oxocholan-24-Oic acid	Generator
3-Dehydrochenodeoxycholate	Generator
3-Oxochenodeoxycholate	Generator
Dehydrochenodeoxycholate	Generator
7a-Hydroxy-3-oxo-5b-cholan-24-Oate	Generator
7a-Hydroxy-3-oxo-5b-cholan-24-Oic acid	Generator
7alpha-Hydroxy-3-oxo-5beta-cholan-24-Oate	Generator
7Α-hydroxy-3-oxo-5β-cholan-24-Oate	Generator
7Α-hydroxy-3-oxo-5β-cholan-24-Oic acid	Generator
7α-Hydroxy-3-oxo-5β-cholanic acid	HMDB
3-Oxo-7α-hydroxy-5β-cholanic acid	HMDB
3-Oxo-7α-hydroxycholan-24-oic acid	HMDB
3-keto-7α-Hydroxy-5β-cholanic acid	HMDB
7α-Hydroxy-3-oxo-5β-cholanoic acid	HMDB
7a-Hydroxy-3-oxo-5b-cholanoic acid	HMDB
7alpha-Hydroxy-3-oxo-5beta-cholanoic acid	HMDB
(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-Hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	Generator, HMDB

Chemical Formula

C₂₄H₃₈O₄

Average Mass

390.5640 Da

Monoisotopic Mass

390.27701 Da

IUPAC Name

(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(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)[C@H](C)CCC(O)=O

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-CIGXQKLNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Monohydroxy bile acid, alcohol, or derivatives
3-oxosteroid
Hydroxysteroid
Oxosteroid
7-hydroxysteroid
3-oxo-5-beta-steroid
Cyclic alcohol
Secondary alcohol
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C24 bile acids, alcohols, and derivatives (LMST04010161 )

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	3.11	ALOGPS
logP	3.92	ChemAxon
logS	-4.4	ALOGPS
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	45.49 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

HMDB0062796

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

5283932

PDB ID

Not Available

ChEBI ID

88097

Good Scents ID

Not Available

References

General References

Deo AK, Bandiera SM: Identification of human hepatic cytochrome p450 enzymes involved in the biotransformation of cholic and chenodeoxycholic acid. Drug Metab Dispos. 2008 Oct;36(10):1983-91. doi: 10.1124/dmd.108.022194. Epub 2008 Jun 26. [PubMed:18583509 ]
Aragozzini F, Canzi E, Ferrari A, Maconi E, Sidjimov A: A study on the mechanism of the epimerization at C-3 of chenodeoxycholic acid by Clostridium perfringens. Biochem J. 1985 Sep 1;230(2):451-5. doi: 10.1042/bj2300451. [PubMed:2864922 ]

Showing NP-Card for 7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid (NP0136233)

MOL for NP0136233 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

3D MOL for NP0136233 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

3D SDF for NP0136233 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

3D-SDF for NP0136233 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

PDB for NP0136233 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

3D PDB for NP0136233 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

SMILES for NP0136233 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

INCHI for NP0136233 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

Structure for NP0136233 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)

3D Structure for NP0136233 (7alpha-Hydroxy-3-oxo-5beta-cholan-24-oic acid)