NP-MRD: Showing NP-Card for 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid (NP0086586)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Show more...Show more...

Record Information

Version

2.0

Created at

2022-05-11 16:25:15 UTC

Updated at

2022-05-11 16:25:15 UTC

NP-MRD ID

NP0086586

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7a,12a-Dihydroxy-3-oxo-4-cholenoic acid

Description

7A,12a-Dihydroxy-3-oxo-4-cholenoic acid, also known as 7alpha,12alpha-dihydroxy-3-oxochol-4-enoate, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. 7A,12a-Dihydroxy-3-oxo-4-cholenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

7a,12a-Dihydroxy-3-oxo-4-cholenoic acid.mol
  Mrv0541 02231218322D          

 32 35  0  0  0  0            999 V2000
   -2.5040   -2.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5040   -1.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895   -1.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895   -2.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0750   -2.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3606   -2.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -2.5001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3539   -1.6751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0684   -1.2626    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8530   -1.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3379   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8530   -0.1826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1079    0.6020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5888    1.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8844    2.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6993    2.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9149    0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -0.4376    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0684    0.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -0.0251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3606   -0.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3606   -1.2626    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0750   -1.6751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0750   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9949    2.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2184    1.5012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184   -2.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    0.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -2.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3606   -2.0876    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -0.8501    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -2.0876    0.0000 H   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
  1  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 17  1  1  0  0  0
 12 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
 16 25  2  0  0  0  0
 16 26  1  0  0  0  0
  1 27  2  0  0  0  0
 20 28  1  6  0  0  0
  7 29  1  6  0  0  0
 22 30  1  6  0  0  0
  8 31  1  1  0  0  0
  9 32  1  6  0  0  0
M  END

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
    3.8546   -0.0472    1.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5438   -0.4568   -0.0095 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9546    0.5691   -1.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3306    1.1320   -0.8445 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4326    0.1870   -0.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -1.0136   -1.1506 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7216    0.6836   -0.7049 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1634   -0.9868   -0.2294 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9810   -2.2090    0.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650   -1.9411    1.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0502   -1.1356    0.3944 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3283   -0.4989    0.7900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9241    0.1210   -0.4430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9677    0.9308   -1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3888    0.3364   -1.3990 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2507   -0.8270   -2.1796 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032   -0.1143   -0.0873 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0499    0.9608    0.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1510    0.8649   -0.0246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9116    1.6917    1.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7123    1.7946   -1.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7663    1.2378   -1.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8174    0.6304   -1.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0085    0.9165   -1.2209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3377   -0.3193   -0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1130   -0.2066    0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6714   -1.1812    1.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2257   -1.5331    1.3654 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0322   -2.7305    0.6681 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0409   -0.1773    2.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7205   -0.6272    1.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2003    1.0175    1.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1887   -1.3475   -0.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2624    1.4295   -1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9407    0.1255   -2.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4761    1.8479   -1.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3904    1.8198    0.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9228    1.2796    0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1648   -1.3878   -1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8354   -3.1441    0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8138   -2.3707    1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8434   -1.4441    2.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1989   -2.9130    1.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2684   -1.8064   -0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1812    0.2922    1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2597   -0.7336   -1.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9493    2.0183   -0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3980    0.9712   -2.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0235    1.0274   -1.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1471   -0.5979   -3.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2097    1.6789    0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9510    1.5935    0.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7890    0.6168    1.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9691    1.0675    2.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0384    2.3370    1.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8050    2.3800    1.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9035    2.2023   -1.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1512    2.7203   -0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1585    2.0502   -2.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3237    0.4127   -2.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0170   -1.1056    0.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2607   -2.1182    1.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9257   -0.7492    2.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8750   -1.7365    2.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1992   -3.4847    1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  2  1  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  7  1  0
  5  6  2  0
  8 17  1  0
 17 18  1  1
 17 15  1  0
 15 16  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 28  1  0
 28 29  1  0
 28 27  1  0
 27 26  1  0
 26 25  2  0
 25 23  1  0
 23 24  2  0
 23 22  1  0
 22 21  1  0
 21 19  1  0
 19 20  1  1
 17 11  1  0
 19 13  1  0
 12 11  1  0
 19 26  1  0
 11 44  1  6
 10 42  1  0
 10 43  1  0
  9 40  1  0
  9 41  1  0
  8 39  1  6
  2 33  1  6
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 15 49  1  6
 16 50  1  0
 14 47  1  0
 14 48  1  0
 13 46  1  6
 12 45  1  1
 28 64  1  1
 29 65  1  0
 27 62  1  0
 27 63  1  0
 25 61  1  0
 22 59  1  0
 22 60  1  0
 21 57  1  0
 21 58  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
M  END

7a,12a-Dihydroxy-3-oxo-4-cholenoic acid.mol
  Mrv0541 02231218322D          

 32 35  0  0  0  0            999 V2000
   -2.5040   -2.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5040   -1.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895   -1.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895   -2.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0750   -2.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3606   -2.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -2.5001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3539   -1.6751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0684   -1.2626    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8530   -1.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3379   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8530   -0.1826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1079    0.6020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5888    1.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8844    2.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6993    2.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9149    0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -0.4376    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0684    0.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -0.0251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3606   -0.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3606   -1.2626    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0750   -1.6751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0750   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9949    2.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2184    1.5012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184   -2.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    0.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -2.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3606   -2.0876    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -0.8501    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -2.0876    0.0000 H   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
  1  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 17  1  1  0  0  0
 12 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
 16 25  2  0  0  0  0
 16 26  1  0  0  0  0
  1 27  2  0  0  0  0
 20 28  1  6  0  0  0
  7 29  1  6  0  0  0
 22 30  1  6  0  0  0
  8 31  1  1  0  0  0
  9 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0086586

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h10,13,16-20,22,26-27H,4-9,11-12H2,1-3H3,(H,28,29)/t13-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

> <INCHI_KEY>
ZZUMXQCSMJCDDC-DFQOQHGMSA-N

> <FORMULA>
C24H36O5

> <MOLECULAR_WEIGHT>
404.5396

> <EXACT_MASS>
404.256274262

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
45.67251982157674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoic acid

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.6441609233333345

> <ALOGPS_LOGS>
-4.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.137674241562625

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.475011880124207

> <JCHEM_PKA_STRONGEST_BASIC>
-0.182516353258798

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
110.58789999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid.mol       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.674  -4.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.674  -3.127   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.340  -2.357   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.340  -5.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.007  -4.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.673  -5.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.661  -4.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.661  -3.127   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.994  -2.357   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.459  -2.833   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.364  -1.587   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.459  -0.341   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.935   1.124   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.966   2.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.518   3.758   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.039   3.999   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.441   1.444   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.994  -0.817   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.994   0.723   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.661  -0.047   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.673  -0.817   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.673  -2.357   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.007  -3.127   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.007  -1.587   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.590   5.437   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.008   2.802   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -6.008  -5.437   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.661   1.493   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.994  -5.437   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      -0.673  -3.897   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.661  -1.587   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.994  -3.897   0.000  0.00  0.00           H+0
CONECT    1    2    4   27                                                  
CONECT    2    1    3                                                       
CONECT    3    2   23                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   29                                                  
CONECT    8    7    9   22   31                                             
CONECT    9    8   10   18   32                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   25   26                                                  
CONECT   17   13                                                            
CONECT   18   12    9   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21    8   23   30                                             
CONECT   23   22    3    5   24                                             
CONECT   24   23                                                            
CONECT   25   16                                                            
CONECT   26   16                                                            
CONECT   27    1                                                            
CONECT   28   20                                                            
CONECT   29    7                                                            
CONECT   30   22                                                            
CONECT   31    8                                                            
CONECT   32    9                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
7alpha,12alpha-Dihydroxy-3-oxochol-4-enoate	ChEBI
7alpha,12alpha-Dihydroxy-3-oxochol-4-enoic acid	ChEBI
7a,12a-Dihydroxy-3-oxochol-4-enoate	Generator
7a,12a-Dihydroxy-3-oxochol-4-enoic acid	Generator
7Α,12α-dihydroxy-3-oxochol-4-enoate	Generator
7Α,12α-dihydroxy-3-oxochol-4-enoic acid	Generator
7a,12a-Dihydroxy-3-oxo-4-cholenoate	Generator
7a,12a-Dihydroxy-3-oxo-chol-4-en-24-Oate	HMDB
7a,12a-Dihydroxy-3-oxo-chol-4-en-24-Oic acid	HMDB
(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-Dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoate	HMDB

Chemical Formula

C₂₄H₃₆O₅

Average Mass

404.5396 Da

Monoisotopic Mass

404.25627 Da

IUPAC Name

(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C24H36O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h10,13,16-20,22,26-27H,4-9,11-12H2,1-3H3,(H,28,29)/t13-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

InChI Key

ZZUMXQCSMJCDDC-DFQOQHGMSA-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

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Dihydroxy bile acid, alcohol, or derivatives
3-oxo-delta-4-steroid
3-oxosteroid
7-hydroxysteroid
Oxosteroid
12-hydroxysteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

7alpha-hydroxy steroid (CHEBI:49269 )
3-oxo Delta(4)-steroid (CHEBI:49269 )
12alpha-hydroxy steroid (CHEBI:49269 )
C24 bile acids, alcohols, and derivatives (LMST04010241 )

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	2.17	ALOGPS
logP	2.64	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.18	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.59 m³·mol⁻¹	ChemAxon
Polarizability	45.67 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