NP-MRD: Showing NP-Card for 5b-Cholestane-3a,7a,12a,25,26-pentol (NP0086897)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-11 16:34:04 UTC

Updated at

2022-05-11 16:34:04 UTC

NP-MRD ID

NP0086897

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5b-Cholestane-3a,7a,12a,25,26-pentol

Description

DG(18:1(11Z)/18:1(11Z)/0:0) Belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. DG(18:1(11Z)/18:1(11Z)/0:0) Is an extremely weak basic (essentially neutral) compound (based on its pKa). Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. CDP-ethanolamine and DG(18:1(11Z)/18:1(11Z)/0:0) Can be converted into cytidine monophosphate and PE(18:1(11Z)/18:1(11Z)); which is mediated by the enzyme choline/ethanolaminephosphotransferase. In humans, DG(18:1(11Z)/18:1(11Z)/0:0) Is involved in phosphatidylethanolamine biosynthesis. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. DG(18:1(11Z)/18:1(11Z)/0:0) Is a diglyceride, or a diacylglycerol (DAG). Phosphatidic acid is then de-phosphorylated to form diacylglycerol. DG(18:1(11Z)/18:1(11Z)/0:0), In particular, consists of two chains of vaccenic acid at the C-1 and C-2 positions. It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. The vaccenic acid moieties are derived from butter fat and animal fat.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231219242D          

 37 40  0  0  1  0            999 V2000
   11.0519  -11.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0519  -12.0736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7663  -12.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4808  -12.0736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4808  -11.2486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7663  -10.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1953  -12.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9097  -12.0736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9097  -11.2486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1953  -10.8361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6242  -10.8361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6242  -10.0111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9097   -9.5986    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1953  -10.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4088  -11.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8938  -10.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4088   -9.7561    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.6638   -8.9715    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1118   -8.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4708   -8.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0228   -9.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8298   -9.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3818   -9.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1888   -9.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1269  -10.6392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6368   -9.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7409  -10.2962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7105   -9.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9097   -8.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2237   -9.6270    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7105  -11.6565    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6242  -12.4861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4808  -12.8986    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3374  -12.4861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1953  -11.6611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4808  -10.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9097  -10.4236    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
  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  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  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
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 24 27  1  0  0  0  0
 12 28  1  1  0  0  0
 13 29  1  6  0  0  0
 17 30  1  6  0  0  0
 11 31  1  6  0  0  0
  8 32  1  6  0  0  0
  4 33  1  1  0  0  0
  2 34  1  6  0  0  0
 10 35  1  6  0  0  0
  5 36  1  1  0  0  0
  9 37  1  1  0  0  0
M  END

     RDKit          3D

 80 83  0  0  0  0  0  0  0  0999 V2000
    2.5903    0.8792   -1.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5521   -0.3932   -0.2392 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7073   -1.2391   -0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0190   -0.6871   -0.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5118    0.6116   -0.6368 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9298    0.7615    0.0138 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8328    0.7199    1.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7088   -0.2809   -0.4376 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5316    2.0578   -0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8221    2.2056    0.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2092   -1.0341   -0.5594 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1213   -2.3831    0.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3318   -2.6864    0.3705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0224   -1.4583   -0.0442 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2682   -1.1173    0.7037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7487    0.1807    0.0904 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7583    1.2752    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4908    0.8802   -0.5308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9052    0.8508   -1.8429 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -0.3662    0.0566 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3738   -0.0590    1.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1478    0.5392    0.4997 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3240    0.6711    1.9729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4609    1.8843   -0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9522    2.1507   -0.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7087    1.1580   -0.9880 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2163    1.6948   -2.1677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7640    0.0406   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0705   -0.4940   -0.1254 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2990   -1.7321   -0.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3381   -2.1733    0.4967 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8401   -3.4183    0.1990 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5916    1.7681   -0.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4262    0.7911   -1.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7101    0.9511   -1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469   -0.0703    0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6538   -2.2658   -0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7060   -1.5041   -1.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8649   -1.4316   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0991   -0.7501    0.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7377    0.6706   -1.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9366    1.5156   -0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9927   -0.3346    1.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8135    1.0098    1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5617    1.4227    1.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9339   -0.9467    0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9444    2.9397   -0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5478    2.0623   -1.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1250    1.4389    0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0689   -1.2026   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6353   -2.4291    1.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -3.1083   -0.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5655   -3.0406    1.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5739   -3.5437   -0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2881   -1.5353   -1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1503   -1.0330    1.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7948   -0.0180   -1.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5049    1.4946    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407    2.1693   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1809    1.7369   -0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674    0.0332   -2.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8368    0.9733    1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1213   -0.7056    1.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4761    0.0132    2.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5695   -0.2454    2.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0825    1.4399    2.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3582    1.0568    2.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0203    1.9897   -1.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0298    2.6542    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3505    2.2608    0.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0740    3.1470   -0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5518    0.7447   -0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3667    2.6678   -2.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0180    0.4125   -2.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3006   -0.8106   -1.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8462   -0.7770    0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0807   -2.5414   -0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8790   -1.6495   -1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9616   -2.3025    1.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3961   -4.1567    0.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 31  1  0
 31 32  1  0
 31 30  1  0
 30 29  1  0
 29 28  1  0
 28 26  1  0
 26 27  1  0
 26 25  1  0
 25 24  1  0
 24 22  1  0
 22 23  1  1
 22 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  1
 11  2  1  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  6
  6  9  1  0
  9 10  1  0
 20 11  1  0
 20 14  1  0
 16 15  1  0
 22 29  1  0
 11 50  1  6
 12 51  1  0
 12 52  1  0
 13 53  1  0
 13 54  1  0
 14 55  1  6
 15 56  1  1
 31 79  1  1
 32 80  1  0
 30 77  1  0
 30 78  1  0
 29 76  1  1
 28 74  1  0
 28 75  1  0
 26 72  1  1
 27 73  1  0
 25 70  1  0
 25 71  1  0
 24 68  1  0
 24 69  1  0
 23 65  1  0
 23 66  1  0
 23 67  1  0
 16 57  1  6
 17 58  1  0
 17 59  1  0
 18 60  1  6
 19 61  1  0
 21 62  1  0
 21 63  1  0
 21 64  1  0
  2 36  1  1
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  7 43  1  0
  7 44  1  0
  7 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
M  END


  Mrv0541 02231219242D          

 37 40  0  0  1  0            999 V2000
   11.0519  -11.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0519  -12.0736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7663  -12.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4808  -12.0736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4808  -11.2486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7663  -10.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1953  -12.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9097  -12.0736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9097  -11.2486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1953  -10.8361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6242  -10.8361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6242  -10.0111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9097   -9.5986    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1953  -10.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4088  -11.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8938  -10.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4088   -9.7561    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.6638   -8.9715    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1118   -8.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4708   -8.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0228   -9.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8298   -9.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3818   -9.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1888   -9.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1269  -10.6392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6368   -9.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7409  -10.2962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7105   -9.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9097   -8.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2237   -9.6270    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7105  -11.6565    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6242  -12.4861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4808  -12.8986    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3374  -12.4861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1953  -11.6611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4808  -10.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9097  -10.4236    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
  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  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  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
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 24 27  1  0  0  0  0
 12 28  1  1  0  0  0
 13 29  1  6  0  0  0
 17 30  1  6  0  0  0
 11 31  1  6  0  0  0
  8 32  1  6  0  0  0
  4 33  1  1  0  0  0
  2 34  1  6  0  0  0
 10 35  1  6  0  0  0
  5 36  1  1  0  0  0
  9 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0086897

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H48O5/c1-16(6-5-10-25(2,32)15-28)19-7-8-20-24-21(14-23(31)27(19,20)4)26(3)11-9-18(29)12-17(26)13-22(24)30/h16-24,28-32H,5-15H2,1-4H3/t16-,17+,18-,19-,20+,21+,22-,23+,24+,25?,26+,27-/m1/s1

> <INCHI_KEY>
XZDHXPDYLPEFQI-FIMPYCPFSA-N

> <FORMULA>
C27H48O5

> <MOLECULAR_WEIGHT>
452.667

> <EXACT_MASS>
452.350174646

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
54.11944453976116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-6,7-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
2.4608679963333326

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.485651631237129

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.038375924904422

> <JCHEM_PKA_STRONGEST_BASIC>
-0.15943471484150906

> <JCHEM_POLAR_SURFACE_AREA>
101.15

> <JCHEM_REFRACTIVITY>
126.25429999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-6,7-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      20.630 -20.997   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.630 -22.537   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.964 -23.307   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.297 -22.537   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.297 -20.997   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.964 -20.227   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.631 -23.307   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.965 -22.537   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.965 -20.997   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.631 -20.227   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      27.299 -20.227   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.299 -18.687   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.965 -17.917   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.631 -18.687   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.763 -20.703   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.668 -19.457   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.763 -18.211   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.239 -16.747   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.209 -15.602   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.745 -16.426   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.776 -17.571   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      33.282 -17.251   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      34.313 -18.395   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      35.819 -18.075   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      33.837 -19.860   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      34.789 -16.931   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      36.850 -19.220   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      27.460 -17.156   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      25.965 -16.377   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      30.284 -17.970   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      27.460 -21.759   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0      27.299 -23.307   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0      23.297 -24.077   0.000  0.00  0.00           H+0
HETATM   34  O   UNK     0      19.296 -23.307   0.000  0.00  0.00           O+0
HETATM   35  H   UNK     0      24.631 -21.767   0.000  0.00  0.00           H+0
HETATM   36  C   UNK     0      23.297 -19.457   0.000  0.00  0.00           C+0
HETATM   37  H   UNK     0      25.965 -19.457   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   33                                             
CONECT    5    4    6   10   36                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   32                                                  
CONECT    9    8   10   11   37                                             
CONECT   10    9    5   14   35                                             
CONECT   11    9   12   15   31                                             
CONECT   12   11   13   17   28                                             
CONECT   13   12   14   29                                                  
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18   30                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23   27                                                       
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   24                                                            
CONECT   28   12                                                            
CONECT   29   13                                                            
CONECT   30   17                                                            
CONECT   31   11                                                            
CONECT   32    8                                                            
CONECT   33    4                                                            
CONECT   34    2                                                            
CONECT   35   10                                                            
CONECT   36    5                                                            
CONECT   37    9                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
3alpha,7alpha,12alpha,25,27-Pentahydroxy-5beta-cholestane	HMDB
5beta-Cholestane-3alpha,7alpha,12alpha,25,26-pentol	HMDB
5β-cholestane-3α,7α,12α,25,26-pentol	HMDB
5 beta-Bufol	MeSH, HMDB
Cholestane-3,7,12,25,26-pentol	MeSH, HMDB

Chemical Formula

C₂₇H₄₈O₅

Average Mass

452.6670 Da

Monoisotopic Mass

452.35017 Da

IUPAC Name

(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-6,7-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol

Traditional Name

(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-6,7-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)(O)CO

InChI Identifier

InChI=1S/C27H48O5/c1-16(6-5-10-25(2,32)15-28)19-7-8-20-24-21(14-23(31)27(19,20)4)26(3)11-9-18(29)12-17(26)13-22(24)30/h16-24,28-32H,5-15H2,1-4H3/t16-,17+,18-,19-,20+,21+,22-,23+,24+,25?,26+,27-/m1/s1

InChI Key

XZDHXPDYLPEFQI-FIMPYCPFSA-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 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Diradylglycerols

Direct Parent

1,2-diacylglycerols

Alternative Parents

Substituents

1,2-acyl-sn-glycerol
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	2.57	ALOGPS
logP	2.46	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	14.04	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	101.15 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	126.25 m³·mol⁻¹	ChemAxon
Polarizability	54.12 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB024382

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

Not Available

Showing NP-Card for 5b-Cholestane-3a,7a,12a,25,26-pentol (NP0086897)

MOL for NP0086897 (5b-Cholestane-3a,7a,12a,25,26-pentol)

3D MOL for NP0086897 (5b-Cholestane-3a,7a,12a,25,26-pentol)

3D SDF for NP0086897 (5b-Cholestane-3a,7a,12a,25,26-pentol)

3D-SDF for NP0086897 (5b-Cholestane-3a,7a,12a,25,26-pentol)

PDB for NP0086897 (5b-Cholestane-3a,7a,12a,25,26-pentol)

3D PDB for NP0086897 (5b-Cholestane-3a,7a,12a,25,26-pentol)

SMILES for NP0086897 (5b-Cholestane-3a,7a,12a,25,26-pentol)

INCHI for NP0086897 (5b-Cholestane-3a,7a,12a,25,26-pentol)

Structure for NP0086897 (5b-Cholestane-3a,7a,12a,25,26-pentol)

3D Structure for NP0086897 (5b-Cholestane-3a,7a,12a,25,26-pentol)