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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:08 UTC

HMDB ID

HMDB0001231

Secondary Accession Numbers

HMDB0006264
HMDB01231
HMDB06264

Metabolite Identification

Common Name

27-Deoxy-5b-cyprinol

Description

27-Deoxy-5b-cyprinol is an intermediate in Bile acid synthesis pathway, in a sequence of reactions catalyzed by sterol 27-hydroxylase (CYP27) in the oxidation of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,27-tetrol into 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acid (PMID: 8496170 ). 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol 3-glucuronide, a metabolite of 27-Deoxy-5b-cyprinol, is the major bile alcohol component in serum from cerebrotendinous xanthomatosis patients (PMID: 7920441 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv0541 02231219002D          

 36 39  0  0  1  0            999 V2000
    7.1116  -19.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1116  -20.5510    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8261  -20.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5406  -20.5510    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5406  -19.7260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8261  -19.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2551  -20.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9696  -20.5510    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9696  -19.7260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2551  -19.3135    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6841  -19.3135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6841  -18.4884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9696  -18.0760    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2551  -18.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4687  -19.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9537  -18.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4687  -18.2335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7228  -17.4515    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1726  -16.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5270  -17.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0772  -17.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8814  -17.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4316  -18.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2358  -18.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1775  -19.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7859  -18.7717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7700  -17.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9696  -17.2537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5406  -18.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3995  -20.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6816  -20.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2808  -18.1049    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5406  -21.3732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9696  -18.9038    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7700  -20.1312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2551  -20.1357    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
 24 26  1  0  0  0  0
 12 27  1  1  0  0  0
 13 28  1  6  0  0  0
  5 29  1  1  0  0  0
  2 30  1  6  0  0  0
  8 31  1  6  0  0  0
 17 32  1  6  0  0  0
  4 33  1  1  0  0  0
  9 34  1  1  0  0  0
 11 35  1  6  0  0  0
 10 36  1  6  0  0  0
M  END

HMDB0001231
     RDKit          3D
27-Deoxy-5b-cyprinol
 79 82  0  0  0  0  0  0  0  0999 V2000
   -4.9910    2.7387    2.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2969    3.9285    3.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852    3.7352    4.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3452    4.8926    5.0465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904    4.3704    2.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328    3.3231    2.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8867    3.8957    1.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2480    2.8982    1.2750 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8024    2.4810    2.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2365    1.7709    0.4253 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6490    2.3792   -0.9221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2309    1.3814   -1.9827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1088    0.1752   -1.1904 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9437   -0.8490   -1.8843 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3210   -1.8943   -0.8503 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1123   -1.2318    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1544   -0.2635    0.9549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0263   -1.0081    1.1509 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8434    0.8218   -0.0095 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0562    1.5739   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0232   -3.0850   -1.4592 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4772   -3.1582   -1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -4.3162   -1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552   -5.5164   -1.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3389   -5.4815   -3.0019 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7835   -6.2643   -4.0472 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6840   -4.1606   -3.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9957   -2.9896   -2.9479 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6106   -2.7494   -3.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124   -1.5293   -2.8979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1230   -1.9127   -2.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3366    1.9310    2.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6455    2.3155    3.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6848    3.1017    1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0290    4.7836    3.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375    2.8163    4.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9875    3.6445    5.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0426    5.6149    5.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7351    5.3159    2.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4347    4.6225    1.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4706    2.4888    1.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7167    2.8665    3.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2192    4.1801    0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130    4.8210    1.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    3.4475    0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6641    3.3626    3.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9008    2.3314    2.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588    1.6519    3.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0624    1.2210    0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466    3.3357   -1.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7618    2.4462   -0.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0255    1.2223   -2.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6929    1.7253   -2.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7949   -0.3174   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8082   -0.4046   -2.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390   -2.1940   -0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -0.6407   -0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4056   -1.9560    1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5927    0.0441    1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5327   -0.5655    1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7211    1.7948    0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6525    1.0513   -1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7306    2.5376   -0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6074   -3.2772    0.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9817   -2.2652   -1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995   -4.0753   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6478   -4.4940    0.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2239   -4.0314   -0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7809   -6.3719   -1.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247   -5.8521   -2.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3114   -6.0172   -2.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7911   -6.3071   -3.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4607   -4.0953   -4.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7955   -3.9542   -3.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955   -2.0758   -3.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7399   -2.5600   -4.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213   -3.6689   -3.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304   -0.7717   -3.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5348   -2.7344   -2.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  6
 15 21  1  0
 21 22  1  1
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 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 19 10  1  0
 28 21  1  0
 19 13  1  0
 30 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  6
  9 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  1
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  1
 14 55  1  6
 15 56  1  1
 16 57  1  0
 16 58  1  0
 17 59  1  1
 18 60  1  0
 20 61  1  0
 20 62  1  0
 20 63  1  0
 22 64  1  0
 22 65  1  0
 22 66  1  0
 23 67  1  0
 23 68  1  0
 24 69  1  0
 24 70  1  0
 25 71  1  1
 26 72  1  0
 27 73  1  0
 27 74  1  0
 28 75  1  1
 29 76  1  0
 29 77  1  0
 30 78  1  6
 31 79  1  0
M  END

  Mrv0541 02231219002D          

 36 39  0  0  1  0            999 V2000
    7.1116  -19.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1116  -20.5510    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8261  -20.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5406  -20.5510    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5406  -19.7260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8261  -19.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2551  -20.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9696  -20.5510    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9696  -19.7260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2551  -19.3135    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6841  -19.3135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6841  -18.4884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    9.2551  -18.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4687  -19.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9537  -18.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4687  -18.2335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7228  -17.4515    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1726  -16.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5270  -17.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0772  -17.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8814  -17.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4316  -18.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2358  -18.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1775  -19.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7859  -18.7717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7700  -17.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9696  -17.2537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5406  -18.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3995  -20.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6816  -20.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2808  -18.1049    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5406  -21.3732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9696  -18.9038    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7700  -20.1312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2551  -20.1357    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
 24 26  1  0  0  0  0
 12 27  1  1  0  0  0
 13 28  1  6  0  0  0
  5 29  1  1  0  0  0
  2 30  1  6  0  0  0
  8 31  1  6  0  0  0
 17 32  1  6  0  0  0
  4 33  1  1  0  0  0
  9 34  1  1  0  0  0
 11 35  1  6  0  0  0
 10 36  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0001231

> <DATABASE_NAME>
hmdb

> <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)CO

> <INCHI_IDENTIFIER>
InChI=1S/C27H48O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h16-25,28-31H,5-15H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
XJZGNVBLVFOSKJ-XZULNKEGSA-N

> <FORMULA>
C27H48O4

> <MOLECULAR_WEIGHT>
436.6676

> <EXACT_MASS>
436.355260024

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
53.375276321490546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.77

> <JCHEM_LOGP>
3.620167761333334

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.2963399055959

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.41832287471465

> <JCHEM_PKA_STRONGEST_BASIC>
-0.1481999506883772

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
124.72619999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-cttl

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001231
     RDKit          3D
27-Deoxy-5b-cyprinol
 79 82  0  0  0  0  0  0  0  0999 V2000
   -4.9910    2.7387    2.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2969    3.9285    3.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852    3.7352    4.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3452    4.8926    5.0465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904    4.3704    2.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328    3.3231    2.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8867    3.8957    1.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2480    2.8982    1.2750 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8024    2.4810    2.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2365    1.7709    0.4253 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6490    2.3792   -0.9221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2309    1.3814   -1.9827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1088    0.1752   -1.1904 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9437   -0.8490   -1.8843 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3210   -1.8943   -0.8503 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1123   -1.2318    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1544   -0.2635    0.9549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0263   -1.0081    1.1509 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8434    0.8218   -0.0095 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0562    1.5739   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0232   -3.0850   -1.4592 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4772   -3.1582   -1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -4.3162   -1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552   -5.5164   -1.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3389   -5.4815   -3.0019 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7835   -6.2643   -4.0472 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6840   -4.1606   -3.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9957   -2.9896   -2.9479 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6106   -2.7494   -3.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124   -1.5293   -2.8979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1230   -1.9127   -2.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3366    1.9310    2.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6455    2.3155    3.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6848    3.1017    1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0290    4.7836    3.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375    2.8163    4.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9875    3.6445    5.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0426    5.6149    5.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7351    5.3159    2.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4347    4.6225    1.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4706    2.4888    1.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7167    2.8665    3.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2192    4.1801    0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130    4.8210    1.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    3.4475    0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6641    3.3626    3.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9008    2.3314    2.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588    1.6519    3.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0624    1.2210    0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466    3.3357   -1.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7618    2.4462   -0.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0255    1.2223   -2.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6929    1.7253   -2.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7949   -0.3174   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8082   -0.4046   -2.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390   -2.1940   -0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -0.6407   -0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4056   -1.9560    1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5927    0.0441    1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5327   -0.5655    1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7211    1.7948    0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6525    1.0513   -1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7306    2.5376   -0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6074   -3.2772    0.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9817   -2.2652   -1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995   -4.0753   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6478   -4.4940    0.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2239   -4.0314   -0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7809   -6.3719   -1.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247   -5.8521   -2.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3114   -6.0172   -2.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7911   -6.3071   -3.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4607   -4.0953   -4.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7955   -3.9542   -3.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955   -2.0758   -3.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7399   -2.5600   -4.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213   -3.6689   -3.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304   -0.7717   -3.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5348   -2.7344   -2.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  6
 15 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 19 10  1  0
 28 21  1  0
 19 13  1  0
 30 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  6
  9 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  1
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  1
 14 55  1  6
 15 56  1  1
 16 57  1  0
 16 58  1  0
 17 59  1  1
 18 60  1  0
 20 61  1  0
 20 62  1  0
 20 63  1  0
 22 64  1  0
 22 65  1  0
 22 66  1  0
 23 67  1  0
 23 68  1  0
 24 69  1  0
 24 70  1  0
 25 71  1  1
 26 72  1  0
 27 73  1  0
 27 74  1  0
 28 75  1  1
 29 76  1  0
 29 77  1  0
 30 78  1  6
 31 79  1  0
M  END

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      13.275 -36.822   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.275 -38.362   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.609 -39.132   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.942 -38.362   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.942 -36.822   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.609 -36.052   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.276 -39.132   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.610 -38.362   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.610 -36.822   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.276 -36.052   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.944 -36.052   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.944 -34.512   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.610 -33.742   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.276 -34.512   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.408 -36.528   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.314 -35.282   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.408 -34.036   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.883 -32.576   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.856 -31.436   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.384 -32.257   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.411 -33.398   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.912 -33.079   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.939 -34.219   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      28.440 -33.900   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      26.465 -35.679   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      29.467 -35.041   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      20.104 -32.985   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.610 -32.207   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      15.942 -35.287   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.946 -39.129   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      19.939 -39.129   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0      22.924 -33.796   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      15.942 -39.897   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      18.610 -35.287   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      20.104 -37.578   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      17.276 -37.587   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   33                                             
CONECT    5    4    6   10   29                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10   11   34                                             
CONECT   10    9    5   14   36                                             
CONECT   11    9   12   15   35                                             
CONECT   12   11   13   17   27                                             
CONECT   13   12   14   28                                                  
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18   32                                             
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                                                  
CONECT   24   23   26                                                       
CONECT   25   23                                                            
CONECT   26   24                                                            
CONECT   27   12                                                            
CONECT   28   13                                                            
CONECT   29    5                                                            
CONECT   30    2                                                            
CONECT   31    8                                                            
CONECT   32   17                                                            
CONECT   33    4                                                            
CONECT   34    9                                                            
CONECT   35   11                                                            
CONECT   36   10                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

COMPND    HMDB0001231
HETATM    1  C1  UNL     1      -4.991   2.739   2.556  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.297   3.929   3.141  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.985   3.735   4.607  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.345   4.893   5.046  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.090   4.370   2.358  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.033   3.323   2.248  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.887   3.896   1.443  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.248   2.898   1.275  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.802   2.481   2.602  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.236   1.771   0.425  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.649   2.379  -0.922  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.231   1.381  -1.983  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.109   0.175  -1.190  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.944  -0.849  -1.884  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.321  -1.894  -0.850  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.112  -1.232   0.240  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.154  -0.263   0.955  1.00  0.00           C  
HETATM   18  O2  UNL     1      -0.026  -1.008   1.151  1.00  0.00           O  
HETATM   19  C17 UNL     1       0.843   0.822  -0.009  1.00  0.00           C  
HETATM   20  C18 UNL     1       2.056   1.574  -0.489  1.00  0.00           C  
HETATM   21  C19 UNL     1       2.023  -3.085  -1.459  1.00  0.00           C  
HETATM   22  C20 UNL     1       3.477  -3.158  -1.043  1.00  0.00           C  
HETATM   23  C21 UNL     1       1.312  -4.316  -1.003  1.00  0.00           C  
HETATM   24  C22 UNL     1       1.455  -5.516  -1.836  1.00  0.00           C  
HETATM   25  C23 UNL     1       2.339  -5.481  -3.002  1.00  0.00           C  
HETATM   26  O3  UNL     1       1.783  -6.264  -4.047  1.00  0.00           O  
HETATM   27  C24 UNL     1       2.684  -4.161  -3.577  1.00  0.00           C  
HETATM   28  C25 UNL     1       1.996  -2.990  -2.948  1.00  0.00           C  
HETATM   29  C26 UNL     1       0.611  -2.749  -3.500  1.00  0.00           C  
HETATM   30  C27 UNL     1       0.012  -1.529  -2.898  1.00  0.00           C  
HETATM   31  O4  UNL     1      -1.123  -1.913  -2.154  1.00  0.00           O  
HETATM   32  H1  UNL     1      -4.337   1.931   2.231  1.00  0.00           H  
HETATM   33  H2  UNL     1      -5.646   2.315   3.372  1.00  0.00           H  
HETATM   34  H3  UNL     1      -5.685   3.102   1.742  1.00  0.00           H  
HETATM   35  H4  UNL     1      -5.029   4.784   3.095  1.00  0.00           H  
HETATM   36  H5  UNL     1      -3.437   2.816   4.826  1.00  0.00           H  
HETATM   37  H6  UNL     1      -4.987   3.645   5.120  1.00  0.00           H  
HETATM   38  H7  UNL     1      -4.043   5.615   5.102  1.00  0.00           H  
HETATM   39  H8  UNL     1      -2.735   5.316   2.805  1.00  0.00           H  
HETATM   40  H9  UNL     1      -3.435   4.622   1.332  1.00  0.00           H  
HETATM   41  H10 UNL     1      -2.471   2.489   1.624  1.00  0.00           H  
HETATM   42  H11 UNL     1      -1.717   2.866   3.182  1.00  0.00           H  
HETATM   43  H12 UNL     1      -1.219   4.180   0.424  1.00  0.00           H  
HETATM   44  H13 UNL     1      -0.513   4.821   1.928  1.00  0.00           H  
HETATM   45  H14 UNL     1       1.055   3.448   0.739  1.00  0.00           H  
HETATM   46  H15 UNL     1       0.664   3.363   3.295  1.00  0.00           H  
HETATM   47  H16 UNL     1       1.901   2.331   2.558  1.00  0.00           H  
HETATM   48  H17 UNL     1       0.259   1.652   3.082  1.00  0.00           H  
HETATM   49  H18 UNL     1      -1.062   1.221   0.874  1.00  0.00           H  
HETATM   50  H19 UNL     1      -0.147   3.336  -1.096  1.00  0.00           H  
HETATM   51  H20 UNL     1      -1.762   2.446  -0.984  1.00  0.00           H  
HETATM   52  H21 UNL     1      -1.026   1.222  -2.738  1.00  0.00           H  
HETATM   53  H22 UNL     1       0.693   1.725  -2.515  1.00  0.00           H  
HETATM   54  H23 UNL     1      -0.795  -0.317  -0.803  1.00  0.00           H  
HETATM   55  H24 UNL     1       1.808  -0.405  -2.384  1.00  0.00           H  
HETATM   56  H25 UNL     1       0.339  -2.194  -0.375  1.00  0.00           H  
HETATM   57  H26 UNL     1       2.950  -0.641  -0.138  1.00  0.00           H  
HETATM   58  H27 UNL     1       2.406  -1.956   1.031  1.00  0.00           H  
HETATM   59  H28 UNL     1       1.593   0.044   1.903  1.00  0.00           H  
HETATM   60  H29 UNL     1      -0.533  -0.566   1.873  1.00  0.00           H  
HETATM   61  H30 UNL     1       2.721   1.795   0.368  1.00  0.00           H  
HETATM   62  H31 UNL     1       2.653   1.051  -1.237  1.00  0.00           H  
HETATM   63  H32 UNL     1       1.731   2.538  -0.957  1.00  0.00           H  
HETATM   64  H33 UNL     1       3.607  -3.277   0.049  1.00  0.00           H  
HETATM   65  H34 UNL     1       3.982  -2.265  -1.455  1.00  0.00           H  
HETATM   66  H35 UNL     1       3.899  -4.075  -1.503  1.00  0.00           H  
HETATM   67  H36 UNL     1       1.648  -4.494   0.063  1.00  0.00           H  
HETATM   68  H37 UNL     1       0.224  -4.031  -0.873  1.00  0.00           H  
HETATM   69  H38 UNL     1       1.781  -6.372  -1.168  1.00  0.00           H  
HETATM   70  H39 UNL     1       0.425  -5.852  -2.166  1.00  0.00           H  
HETATM   71  H40 UNL     1       3.311  -6.017  -2.778  1.00  0.00           H  
HETATM   72  H41 UNL     1       0.791  -6.307  -3.916  1.00  0.00           H  
HETATM   73  H42 UNL     1       2.461  -4.095  -4.684  1.00  0.00           H  
HETATM   74  H43 UNL     1       3.795  -3.954  -3.535  1.00  0.00           H  
HETATM   75  H44 UNL     1       2.596  -2.076  -3.237  1.00  0.00           H  
HETATM   76  H45 UNL     1       0.740  -2.560  -4.602  1.00  0.00           H  
HETATM   77  H46 UNL     1       0.021  -3.669  -3.362  1.00  0.00           H  
HETATM   78  H47 UNL     1      -0.330  -0.772  -3.609  1.00  0.00           H  
HETATM   79  H48 UNL     1      -1.535  -2.734  -2.509  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    5   35
CONECT    3    4   36   37
CONECT    4   38
CONECT    5    6   39   40
CONECT    6    7   41   42
CONECT    7    8   43   44
CONECT    8    9   10   45
CONECT    9   46   47   48
CONECT   10   11   19   49
CONECT   11   12   50   51
CONECT   12   13   52   53
CONECT   13   14   19   54
CONECT   14   15   30   55
CONECT   15   16   21   56
CONECT   16   17   57   58
CONECT   17   18   19   59
CONECT   18   60
CONECT   19   20
CONECT   20   61   62   63
CONECT   21   22   23   28
CONECT   22   64   65   66
CONECT   23   24   67   68
CONECT   24   25   69   70
CONECT   25   26   27   71
CONECT   26   72
CONECT   27   28   73   74
CONECT   28   29   75
CONECT   29   30   76   77
CONECT   30   31   78
CONECT   31   79
END

HMDB0001231
     RDKit          3D
27-Deoxy-5b-cyprinol
 79 82  0  0  0  0  0  0  0  0999 V2000
   -4.9910    2.7387    2.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2969    3.9285    3.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852    3.7352    4.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3452    4.8926    5.0465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904    4.3704    2.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328    3.3231    2.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8867    3.8957    1.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2480    2.8982    1.2750 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8024    2.4810    2.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2365    1.7709    0.4253 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6490    2.3792   -0.9221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2309    1.3814   -1.9827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1088    0.1752   -1.1904 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9437   -0.8490   -1.8843 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3210   -1.8943   -0.8503 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1123   -1.2318    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1544   -0.2635    0.9549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0263   -1.0081    1.1509 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8434    0.8218   -0.0095 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0562    1.5739   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0232   -3.0850   -1.4592 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4772   -3.1582   -1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -4.3162   -1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552   -5.5164   -1.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3389   -5.4815   -3.0019 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7835   -6.2643   -4.0472 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6840   -4.1606   -3.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9957   -2.9896   -2.9479 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6106   -2.7494   -3.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124   -1.5293   -2.8979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1230   -1.9127   -2.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3366    1.9310    2.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6455    2.3155    3.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6848    3.1017    1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0290    4.7836    3.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375    2.8163    4.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9875    3.6445    5.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0426    5.6149    5.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7351    5.3159    2.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4347    4.6225    1.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4706    2.4888    1.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7167    2.8665    3.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2192    4.1801    0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130    4.8210    1.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    3.4475    0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6641    3.3626    3.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9008    2.3314    2.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588    1.6519    3.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0624    1.2210    0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466    3.3357   -1.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7618    2.4462   -0.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0255    1.2223   -2.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6929    1.7253   -2.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7949   -0.3174   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8082   -0.4046   -2.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390   -2.1940   -0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -0.6407   -0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4056   -1.9560    1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5927    0.0441    1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5327   -0.5655    1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7211    1.7948    0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6525    1.0513   -1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7306    2.5376   -0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6074   -3.2772    0.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9817   -2.2652   -1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995   -4.0753   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6478   -4.4940    0.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2239   -4.0314   -0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7809   -6.3719   -1.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247   -5.8521   -2.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3114   -6.0172   -2.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7911   -6.3071   -3.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4607   -4.0953   -4.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7955   -3.9542   -3.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955   -2.0758   -3.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7399   -2.5600   -4.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213   -3.6689   -3.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304   -0.7717   -3.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5348   -2.7344   -2.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  6
 15 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 19 10  1  0
 28 21  1  0
 19 13  1  0
 30 14  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  6
  9 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  1
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  1
 14 55  1  6
 15 56  1  1
 16 57  1  0
 16 58  1  0
 17 59  1  1
 18 60  1  0
 20 61  1  0
 20 62  1  0
 20 63  1  0
 22 64  1  0
 22 65  1  0
 22 66  1  0
 23 67  1  0
 23 68  1  0
 24 69  1  0
 24 70  1  0
 25 71  1  1
 26 72  1  0
 27 73  1  0
 27 74  1  0
 28 75  1  1
 29 76  1  0
 29 77  1  0
 30 78  1  6
 31 79  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3alpha,5beta,7alpha,12alpha)-Cholestane-3,7,12,26-tetrol	ChEBI
3alpha,7alpha,12alpha,26-Tetrahydroxy-5beta-cholestane	ChEBI
5beta-Cholestane 3alpha,7alpha,12alpha,27-tetrol	ChEBI
5beta-Cholestane-3alpha,7alpha,12alpha,26-tetraol	ChEBI
Cholestane-3,7,12,26(27)-tetrol	ChEBI
Cholestane-3,7,12,26-tetrol	ChEBI
Cholestane-3,7,12,27-tetrol	ChEBI
5beta-Cholestane-3alpha,7alpha,12alpha,26-tetrol	Kegg
(3a,5b,7a,12a)-Cholestane-3,7,12,26-tetrol	Generator
(3Α,5β,7α,12α)-cholestane-3,7,12,26-tetrol	Generator
3a,7a,12a,26-Tetrahydroxy-5b-cholestane	Generator
3Α,7α,12α,26-tetrahydroxy-5β-cholestane	Generator
5b-Cholestane 3a,7a,12a,27-tetrol	Generator
5Β-cholestane 3α,7α,12α,27-tetrol	Generator
5b-Cholestane-3a,7a,12a,26-tetraol	Generator
5Β-cholestane-3α,7α,12α,26-tetraol	Generator
5b-Cholestane-3a,7a,12a,26-tetrol	Generator
5Β-cholestane-3α,7α,12α,26-tetrol	Generator
(25R)-5-beta-Cholestane-3-alpha,7-alpha,12-alpha,26-tetraol	HMDB
5-b-Cholestane-3a-7-tetraol	HMDB
5-beta-Cholestane-3-alpha-7-alpha-12-alpha-26-tetraol	HMDB
5-beta-Cholestane-3a-7-tetraol	HMDB
5beta-Cholestane-3alpha,7alpha,12alpha,27-tetraol	HMDB
5beta-Cholestane-3alpha,7alpha,12alpha,27-tetrol	HMDB
5beta-Cholestane-3alpha,7alpha,12alpha,27alpha-tetrol	HMDB
5 beta-Cholestane-3alpha,7alpha,12alpha,26-tetrol	HMDB
5-CTTL	HMDB
Cholestane-3,7,12,26-tetrol, (3alpha,5alpha,7alpha,12alpha)-isomer	HMDB

Chemical Formula

C₂₇H₄₈O₄

Average Molecular Weight

436.6676

Monoisotopic Molecular Weight

436.355260024

IUPAC Name

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

Traditional Name

5-cttl

CAS Registry Number

862-53-3

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)CO

InChI Identifier

InChI=1S/C27H48O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h16-25,28-31H,5-15H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

XJZGNVBLVFOSKJ-XZULNKEGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl 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

Tetrahydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

26-hydroxysteroid
Tetrahydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
12-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Fatty alcohol
Fatty acyl
Cyclic alcohol
Secondary alcohol
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3alpha-hydroxy steroid (CHEBI:17278 )
7alpha-hydroxy steroid (CHEBI:17278 )
12alpha-hydroxy steroid (CHEBI:17278 )
26-hydroxy steroid (CHEBI:17278 )
C27 bile acids, alcohols, and derivatives (C05446 )
C27 bile acids, alcohols, and derivatives (LMST04030014 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0001231)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0001231)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0001231)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001231)

Source

Endogenous

Endogenous (HMDB: HMDB0001231)

Animal

Animal (HMDB: HMDB0001231)

Exogenous

Food

Food (HMDB: HMDB0001231)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0001231)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0001231)

Biochemical pathway

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (HMDB: HMDB0001231)
27-Hydroxylase Deficiency (PathBank: SMP0120652)
Cerebrotendinous Xanthomatosis (CTX) (PathBank: SMP0120683)
Familial Hypercholanemia (FHCA) (PathBank: SMP0120697)
Zellweger Syndrome (PathBank: SMP0120715)
Congenital Bile Acid Synthesis Defect Type II (PathBank: SMP0120687)
Congenital Bile Acid Synthesis Defect Type III (PathBank: SMP0120688)

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0001231)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Lipid metabolism pathway (HMDB: HMDB0001231)

Cellular process

Cell signaling (HMDB: HMDB0001231)

Biochemical process

Lipid transport (HMDB: HMDB0001231)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0001231)

Molecular messenger

Hormone (HMDB: HMDB0001231)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0001231)

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	3.77	ALOGPS
logP	3.62	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	17.42	ChemAxon
pKa (Strongest Basic)	-0.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	124.73 m³·mol⁻¹	ChemAxon
Polarizability	53.38 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	207.169	31661259
DarkChem	[M-H]-	198.985	31661259
AllCCS	[M+H]+	212.005	32859911
AllCCS	[M-H]-	205.635	32859911
DeepCCS	[M-2H]-	242.828	30932474
DeepCCS	[M+Na]+	216.846	30932474
AllCCS	[M+H]+	212.0	32859911
AllCCS	[M+H-H2O]+	210.2	32859911
AllCCS	[M+NH4]+	213.7	32859911
AllCCS	[M+Na]+	214.2	32859911
AllCCS	[M-H]-	205.6	32859911
AllCCS	[M+Na-2H]-	207.9	32859911
AllCCS	[M+HCOO]-	210.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
27-Deoxy-5b-cyprinol	[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)CO	3195.1	Standard polar	33892256
27-Deoxy-5b-cyprinol	[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)CO	3543.9	Standard non polar	33892256
27-Deoxy-5b-cyprinol	[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)CO	3905.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
27-Deoxy-5b-cyprinol,1TMS,isomer #1	CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3494.1	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,1TMS,isomer #2	CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3549.0	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,1TMS,isomer #3	CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3542.2	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,1TMS,isomer #4	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O)CO[Si](C)(C)C	3545.6	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,2TMS,isomer #1	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C)CO[Si](C)(C)C	3441.2	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,2TMS,isomer #2	CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3466.8	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,2TMS,isomer #3	CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3444.4	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,2TMS,isomer #4	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O)CO[Si](C)(C)C	3504.1	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,2TMS,isomer #5	CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3478.4	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,2TMS,isomer #6	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O)CO[Si](C)(C)C	3500.5	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,3TMS,isomer #1	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C)CO[Si](C)(C)C	3445.8	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,3TMS,isomer #2	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C)CO[Si](C)(C)C	3430.8	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,3TMS,isomer #3	CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3450.1	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,3TMS,isomer #4	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O)CO[Si](C)(C)C	3432.2	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,4TMS,isomer #1	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C)CO[Si](C)(C)C	3445.7	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,1TBDMS,isomer #1	CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3707.1	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,1TBDMS,isomer #2	CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3759.4	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,1TBDMS,isomer #3	CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3765.1	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,1TBDMS,isomer #4	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O)CO[Si](C)(C)C(C)(C)C	3777.5	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,2TBDMS,isomer #1	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	3874.7	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,2TBDMS,isomer #2	CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3908.9	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,2TBDMS,isomer #3	CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3874.5	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,2TBDMS,isomer #4	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O)CO[Si](C)(C)C(C)(C)C	3979.4	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,2TBDMS,isomer #5	CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3913.7	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,2TBDMS,isomer #6	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O)CO[Si](C)(C)C(C)(C)C	3946.1	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,3TBDMS,isomer #1	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	4104.0	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,3TBDMS,isomer #2	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	4077.9	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,3TBDMS,isomer #3	CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4094.2	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,3TBDMS,isomer #4	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O)CO[Si](C)(C)C(C)(C)C	4125.4	Semi standard non polar	33892256
27-Deoxy-5b-cyprinol,4TBDMS,isomer #1	CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	4315.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 27-Deoxy-5b-cyprinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05vx-0539800000-97d0e900e0ff8088e8ae	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 27-Deoxy-5b-cyprinol GC-MS (3 TMS) - 70eV, Positive	splash10-000i-2210079000-59774cc66a8ee849736f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 27-Deoxy-5b-cyprinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 27-Deoxy-5b-cyprinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 10V, Positive-QTOF	splash10-0uxr-0000900000-a7bb325d6ee8da922144	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 20V, Positive-QTOF	splash10-0uxr-1004900000-c638ee962db83c052bc5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 40V, Positive-QTOF	splash10-000i-2109100000-69c195557b16f6759fe2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 10V, Negative-QTOF	splash10-00kr-0001900000-ac185007bede2c767651	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 20V, Negative-QTOF	splash10-00kr-0003900000-c665bc9fb94b91ab203e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 40V, Negative-QTOF	splash10-000i-2009400000-5648c1610aafe0315c85	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 10V, Negative-QTOF	splash10-000i-0000900000-70eabfb538b202d65e50	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 20V, Negative-QTOF	splash10-000i-0000900000-96d84b6ae4900e35a01e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 40V, Negative-QTOF	splash10-001i-0002900000-aedbb2b65b87f50fb926	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 10V, Positive-QTOF	splash10-0fri-0000900000-260248684581f7f3ef51	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 20V, Positive-QTOF	splash10-0udi-4322900000-e31a265ff7b793fc8577	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 40V, Positive-QTOF	splash10-0a4i-9421000000-a3832dd065b12eca2a9a	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Primary bile acid biosynthesis	Not Available
Congenital Bile Acid Synthesis Defect Type II		Not Available
Congenital Bile Acid Synthesis Defect Type III		Not Available
Familial Hypercholanemia (FHCA)		Not Available
Zellweger Syndrome		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022502

KNApSAcK ID

Not Available

Chemspider ID

167758

KEGG Compound ID

C05446

BioCyc ID

Not Available

BiGG ID

45828

Wikipedia Link

Not Available

METLIN ID

6095

PubChem Compound

193321

PDB ID

Not Available

ChEBI ID

17278

Food Biomarker Ontology

Not Available

VMH ID

M01092

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Holmberg-Betsholtz I, Lund E, Bjorkhem I, Wikvall K: Sterol 27-hydroxylase in bile acid biosynthesis. Mechanism of oxidation of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,27-tetrol into 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acid. J Biol Chem. 1993 May 25;268(15):11079-85. [PubMed:8496170 ]
Ohshima A, Kuramoto T, Hoshita T: Biochemical studies of inherited diseases related to abnormal cholesterol metabolism. I. High-performance liquid chromatographic analysis of bile alcohol glucuronides in cerebrotendinous xanthomatosis. Biol Pharm Bull. 1994 May;17(5):721-3. [PubMed:7920441 ]

Enzymes

Enzyme Details

1. Sterol 26-hydroxylase, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:: CYP27A1
Uniprot ID:: Q02318
Molecular weight:: 60234.28

Reactions

5beta-Cholestane-3alpha,7alpha,12alpha-triol + Oxygen + NADPH → 27-Deoxy-5b-cyprinol + NADP + Water	details
27-Deoxy-5b-cyprinol → 3a,7a,12a-Trihydroxy-5b-cholestan-26-al	details

Showing metabocard for 27-Deoxy-5b-cyprinol (HMDB0001231)

MOL for HMDB0001231 (27-Deoxy-5b-cyprinol)

3D MOL for HMDB0001231 (27-Deoxy-5b-cyprinol)

3D SDF for HMDB0001231 (27-Deoxy-5b-cyprinol)

3D-SDF for HMDB0001231 (27-Deoxy-5b-cyprinol)

PDB for HMDB0001231 (27-Deoxy-5b-cyprinol)

3D PDB for HMDB0001231 (27-Deoxy-5b-cyprinol)

SMILES for HMDB0001231 (27-Deoxy-5b-cyprinol)

INCHI for HMDB0001231 (27-Deoxy-5b-cyprinol)

Structure for HMDB0001231 (27-Deoxy-5b-cyprinol)

3D Structure for HMDB0001231 (27-Deoxy-5b-cyprinol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions