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enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015180

Secondary Accession Numbers

HMDB15180

Metabolite Identification

Common Name

Lubiprostone

Description

Lubiprostone is a medication used in the management of idiopathic chronic constipation. It is a bicyclic fatty acid (prostaglandin E1 derivative) which acts by specifically activating ClC-2 chloride channels on the apical aspect of gastrointestinal epithelial cells, producing a chloride-rich fluid secretion. These secretions soften the stool, increase motility, and promote spontaneous bowel movements (SBM).

Structure

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

1046
  Mrv0541 02231215122D          

 29 30  0  0  1  0            999 V2000
    4.1251   -1.2943    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8430   -2.8947    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6646   -2.5318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8069   -2.9319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4663   -1.7068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4140    2.7744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0558    3.2183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3791   -1.2943    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3791   -2.1193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1598   -1.0429    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6646   -0.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1598   -2.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501   -2.1193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9501   -1.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6412   -1.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4160   -0.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -2.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2233   -0.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -2.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4796    0.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -1.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2869    0.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5432    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3505    1.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6068    2.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4489   -0.6380    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4489   -2.7757    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2 17  1  0  0  0  0
  3  9  1  0  0  0  0
  3 13  1  0  0  0  0
 13  4  1  6  0  0  0
  5 15  2  0  0  0  0
  6 27  1  0  0  0  0
  7 27  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
  8 28  1  1  0  0  0
  9 12  1  0  0  0  0
  9 29  1  6  0  0  0
 10 15  1  0  0  0  0
 10 16  1  6  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 26  1  0  0  0  0
 24 25  1  0  0  0  0
 25 27  1  0  0  0  0
M  END

HMDB0015180
     RDKit          3D
Lubiprostone
 59 60  0  0  0  0  0  0  0  0999 V2000
   -8.3463   -0.5371   -1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8550   -0.1143   -1.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1076   -1.0395   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6319   -0.8004   -0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3188    0.5546    0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8137    0.8144    1.5446 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7951    1.5029   -0.5746 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8097    0.8153    0.3800 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7251    2.1482    0.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236   -0.0647    1.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8512   -0.7312    0.8834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3803   -0.3114   -0.4516 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0782   -0.1272   -0.6718 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8909   -0.1714    0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3633    0.0013    0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1188   -0.0962    1.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6064    0.0666    1.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1959   -0.9613    0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6739   -0.7455    0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9874    0.5500   -0.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2101    0.8762   -0.2339 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0722    1.4233   -0.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2008    1.0920   -1.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604    1.7510   -1.7548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1755    1.3862   -1.9898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326    1.0725   -0.7285 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2877    0.8755   -0.9081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4891   -1.4932   -1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6331   -0.5461   -0.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9160    0.2828   -1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5528   -0.1646   -2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8845    0.9417   -0.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5867   -0.9357    0.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3587   -2.0765   -0.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2601   -0.9730   -1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1518   -1.6238    0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0247    2.7374    0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8666    0.4998    2.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8678   -0.8261    1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0479   -1.8273    0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0383   -0.6108    1.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826   -0.9504   -1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -1.0239   -1.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5404    0.6048    1.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7830   -1.2057    0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7552   -0.7990   -0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347    1.0080   -0.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526   -1.0206    2.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710    0.7612    2.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8666    1.0746    1.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0709   -0.0910    2.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7795   -0.9050   -0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0758   -2.0015    0.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1693   -0.8569    1.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0700   -1.5482   -0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7424    1.4828   -1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    0.5783   -2.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3126    2.3956   -2.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6639    1.8201    0.0181 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
  4  5  1  0
  5  6  1  0
  5  7  1  0
  5  8  1  0
  8  9  1  1
  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
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 13 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27  8  1  0
 26 12  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  6
 13 43  1  6
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  1
M  END

1046
  Mrv0541 02231215122D          

 29 30  0  0  1  0            999 V2000
    4.1251   -1.2943    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8430   -2.8947    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6646   -2.5318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8069   -2.9319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4663   -1.7068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4140    2.7744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0558    3.2183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3791   -1.2943    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3791   -2.1193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1598   -1.0429    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6646   -0.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1598   -2.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501   -2.1193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9501   -1.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6412   -1.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4160   -0.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -2.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2233   -0.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -2.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4796    0.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -1.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2869    0.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5432    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3505    1.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6068    2.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4489   -0.6380    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4489   -2.7757    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2 17  1  0  0  0  0
  3  9  1  0  0  0  0
  3 13  1  0  0  0  0
 13  4  1  6  0  0  0
  5 15  2  0  0  0  0
  6 27  1  0  0  0  0
  7 27  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
  8 28  1  1  0  0  0
  9 12  1  0  0  0  0
  9 29  1  6  0  0  0
 10 15  1  0  0  0  0
 10 16  1  6  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 26  1  0  0  0  0
 24 25  1  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015180

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC(=O)[C@@H](CCCCCCC(O)=O)[C@@]1([H])CC[C@@](O)(O2)C(F)(F)CCCC

> <INCHI_IDENTIFIER>
InChI=1S/C20H32F2O5/c1-2-3-11-19(21,22)20(26)12-10-15-14(16(23)13-17(15)27-20)8-6-4-5-7-9-18(24)25/h14-15,17,26H,2-13H2,1H3,(H,24,25)/t14-,15+,17+,20+/m0/s1

> <INCHI_KEY>
WGFOBBZOWHGYQH-DKYLXPRQSA-N

> <FORMULA>
C20H32F2O5

> <MOLECULAR_WEIGHT>
390.4619

> <EXACT_MASS>
390.221780544

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.51836490961102

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
4.563896638333332

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.6804921656489

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.304478433584986

> <JCHEM_PKA_STRONGEST_BASIC>
-4.395927408994909

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
95.6009

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lubiprostone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015180
     RDKit          3D
Lubiprostone
 59 60  0  0  0  0  0  0  0  0999 V2000
   -8.3463   -0.5371   -1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8550   -0.1143   -1.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1076   -1.0395   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6319   -0.8004   -0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3188    0.5546    0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8137    0.8144    1.5446 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7951    1.5029   -0.5746 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8097    0.8153    0.3800 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7251    2.1482    0.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236   -0.0647    1.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8512   -0.7312    0.8834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3803   -0.3114   -0.4516 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0782   -0.1272   -0.6718 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8909   -0.1714    0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3633    0.0013    0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1188   -0.0962    1.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6064    0.0666    1.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1959   -0.9613    0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6739   -0.7455    0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9874    0.5500   -0.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2101    0.8762   -0.2339 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0722    1.4233   -0.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2008    1.0920   -1.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604    1.7510   -1.7548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1755    1.3862   -1.9898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326    1.0725   -0.7285 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2877    0.8755   -0.9081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4891   -1.4932   -1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6331   -0.5461   -0.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9160    0.2828   -1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5528   -0.1646   -2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8845    0.9417   -0.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5867   -0.9357    0.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3587   -2.0765   -0.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2601   -0.9730   -1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1518   -1.6238    0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0247    2.7374    0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8666    0.4998    2.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8678   -0.8261    1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0479   -1.8273    0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0383   -0.6108    1.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826   -0.9504   -1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -1.0239   -1.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5404    0.6048    1.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7830   -1.2057    0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7552   -0.7990   -0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347    1.0080   -0.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526   -1.0206    2.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710    0.7612    2.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8666    1.0746    1.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0709   -0.0910    2.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7795   -0.9050   -0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0758   -2.0015    0.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1693   -0.8569    1.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0700   -1.5482   -0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7424    1.4828   -1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    0.5783   -2.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3126    2.3956   -2.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6639    1.8201    0.0181 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
  4  5  1  0
  5  6  1  0
  5  7  1  0
  5  8  1  0
  8  9  1  1
  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
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 13 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27  8  1  0
 26 12  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  6
 13 43  1  6
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1046                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       7.700  -2.416   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0       7.174  -5.403   0.000  0.00  0.00           F+0
HETATM    3  O   UNK     0      10.574  -4.726   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.973  -5.473   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      15.804  -3.186   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      21.306   5.179   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      18.771   6.007   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.908  -2.416   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.908  -3.956   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.365  -1.947   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.574  -1.646   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.365  -4.425   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.240  -3.956   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.240  -2.416   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.264  -3.186   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.843  -0.483   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.700  -3.956   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.350  -0.165   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.160  -3.956   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.829   1.298   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.390  -2.622   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.336   1.616   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.850  -2.622   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.814   3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.321   3.398   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.080  -1.289   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.799   4.861   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      12.038  -1.191   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      12.038  -5.181   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   17                                                            
CONECT    3    9   13                                                       
CONECT    4   13                                                            
CONECT    5   15                                                            
CONECT    6   27                                                            
CONECT    7   27                                                            
CONECT    8    9   10   11   28                                             
CONECT    9    3    8   12   29                                             
CONECT   10    8   15   16                                                  
CONECT   11    8   14                                                       
CONECT   12    9   15                                                       
CONECT   13    3    4   14   17                                             
CONECT   14   11   13                                                       
CONECT   15    5   10   12                                                  
CONECT   16   10   18                                                       
CONECT   17    1    2   13   19                                             
CONECT   18   16   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   26                                                       
CONECT   24   22   25                                                       
CONECT   25   24   27                                                       
CONECT   26   23                                                            
CONECT   27    6    7   25                                                  
CONECT   28    8                                                            
CONECT   29    9                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

COMPND    HMDB0015180
HETATM    1  C1  UNL     1      -8.346  -0.537  -1.112  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.855  -0.114  -1.157  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.108  -1.039  -0.252  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.632  -0.800  -0.196  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.319   0.555   0.294  1.00  0.00           C  
HETATM    6  F1  UNL     1      -4.814   0.814   1.545  1.00  0.00           F  
HETATM    7  F2  UNL     1      -4.795   1.503  -0.575  1.00  0.00           F  
HETATM    8  C6  UNL     1      -2.810   0.815   0.380  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.725   2.148   0.863  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.124  -0.065   1.337  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.851  -0.731   0.883  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.380  -0.311  -0.452  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.078  -0.127  -0.672  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.891  -0.171   0.570  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.363   0.001   0.340  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.119  -0.096   1.680  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.606   0.067   1.476  1.00  0.00           C  
HETATM   18  C15 UNL     1       6.196  -0.961   0.575  1.00  0.00           C  
HETATM   19  C16 UNL     1       7.674  -0.746   0.422  1.00  0.00           C  
HETATM   20  C17 UNL     1       7.987   0.550  -0.191  1.00  0.00           C  
HETATM   21  O2  UNL     1       9.210   0.876  -0.234  1.00  0.00           O  
HETATM   22  O3  UNL     1       7.072   1.423  -0.717  1.00  0.00           O  
HETATM   23  C18 UNL     1       1.201   1.092  -1.496  1.00  0.00           C  
HETATM   24  O4  UNL     1       2.160   1.751  -1.755  1.00  0.00           O  
HETATM   25  C19 UNL     1      -0.175   1.386  -1.990  1.00  0.00           C  
HETATM   26  C20 UNL     1      -0.933   1.073  -0.729  1.00  0.00           C  
HETATM   27  O5  UNL     1      -2.288   0.876  -0.908  1.00  0.00           O  
HETATM   28  H1  UNL     1      -8.489  -1.493  -1.616  1.00  0.00           H  
HETATM   29  H2  UNL     1      -8.633  -0.546  -0.046  1.00  0.00           H  
HETATM   30  H3  UNL     1      -8.916   0.283  -1.585  1.00  0.00           H  
HETATM   31  H4  UNL     1      -6.553  -0.165  -2.211  1.00  0.00           H  
HETATM   32  H5  UNL     1      -6.884   0.942  -0.811  1.00  0.00           H  
HETATM   33  H6  UNL     1      -6.587  -0.936   0.763  1.00  0.00           H  
HETATM   34  H7  UNL     1      -6.359  -2.076  -0.581  1.00  0.00           H  
HETATM   35  H8  UNL     1      -4.260  -0.973  -1.255  1.00  0.00           H  
HETATM   36  H9  UNL     1      -4.152  -1.624   0.375  1.00  0.00           H  
HETATM   37  H10 UNL     1      -3.025   2.737   0.127  1.00  0.00           H  
HETATM   38  H11 UNL     1      -1.867   0.500   2.285  1.00  0.00           H  
HETATM   39  H12 UNL     1      -2.868  -0.826   1.718  1.00  0.00           H  
HETATM   40  H13 UNL     1      -1.048  -1.827   0.847  1.00  0.00           H  
HETATM   41  H14 UNL     1      -0.038  -0.611   1.628  1.00  0.00           H  
HETATM   42  H15 UNL     1      -0.783  -0.950  -1.289  1.00  0.00           H  
HETATM   43  H16 UNL     1       1.427  -1.024  -1.287  1.00  0.00           H  
HETATM   44  H17 UNL     1       1.540   0.605   1.318  1.00  0.00           H  
HETATM   45  H18 UNL     1       1.783  -1.206   0.994  1.00  0.00           H  
HETATM   46  H19 UNL     1       3.755  -0.799  -0.287  1.00  0.00           H  
HETATM   47  H20 UNL     1       3.535   1.008  -0.104  1.00  0.00           H  
HETATM   48  H21 UNL     1       3.853  -1.021   2.207  1.00  0.00           H  
HETATM   49  H22 UNL     1       3.771   0.761   2.289  1.00  0.00           H  
HETATM   50  H23 UNL     1       5.867   1.075   1.159  1.00  0.00           H  
HETATM   51  H24 UNL     1       6.071  -0.091   2.493  1.00  0.00           H  
HETATM   52  H25 UNL     1       5.779  -0.905  -0.473  1.00  0.00           H  
HETATM   53  H26 UNL     1       6.076  -2.002   0.975  1.00  0.00           H  
HETATM   54  H27 UNL     1       8.169  -0.857   1.420  1.00  0.00           H  
HETATM   55  H28 UNL     1       8.070  -1.548  -0.264  1.00  0.00           H  
HETATM   56  H29 UNL     1       6.742   1.483  -1.655  1.00  0.00           H  
HETATM   57  H30 UNL     1      -0.406   0.578  -2.717  1.00  0.00           H  
HETATM   58  H31 UNL     1      -0.313   2.396  -2.367  1.00  0.00           H  
HETATM   59  H32 UNL     1      -0.664   1.820   0.018  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6    7    8
CONECT    8    9   10   27
CONECT    9   37
CONECT   10   11   38   39
CONECT   11   12   40   41
CONECT   12   13   26   42
CONECT   13   14   23   43
CONECT   14   15   44   45
CONECT   15   16   46   47
CONECT   16   17   48   49
CONECT   17   18   50   51
CONECT   18   19   52   53
CONECT   19   20   54   55
CONECT   20   21   21   22
CONECT   22   56
CONECT   23   24   24   25
CONECT   25   26   57   58
CONECT   26   27   59
END

HMDB0015180
     RDKit          3D
Lubiprostone
 59 60  0  0  0  0  0  0  0  0999 V2000
   -8.3463   -0.5371   -1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8550   -0.1143   -1.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1076   -1.0395   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6319   -0.8004   -0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3188    0.5546    0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8137    0.8144    1.5446 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7951    1.5029   -0.5746 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8097    0.8153    0.3800 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7251    2.1482    0.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236   -0.0647    1.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8512   -0.7312    0.8834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3803   -0.3114   -0.4516 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0782   -0.1272   -0.6718 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8909   -0.1714    0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3633    0.0013    0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1188   -0.0962    1.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6064    0.0666    1.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1959   -0.9613    0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6739   -0.7455    0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9874    0.5500   -0.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2101    0.8762   -0.2339 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0722    1.4233   -0.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2008    1.0920   -1.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604    1.7510   -1.7548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1755    1.3862   -1.9898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326    1.0725   -0.7285 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2877    0.8755   -0.9081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4891   -1.4932   -1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6331   -0.5461   -0.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9160    0.2828   -1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5528   -0.1646   -2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8845    0.9417   -0.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5867   -0.9357    0.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3587   -2.0765   -0.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2601   -0.9730   -1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1518   -1.6238    0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0247    2.7374    0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8666    0.4998    2.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8678   -0.8261    1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0479   -1.8273    0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0383   -0.6108    1.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826   -0.9504   -1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -1.0239   -1.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5404    0.6048    1.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7830   -1.2057    0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7552   -0.7990   -0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347    1.0080   -0.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526   -1.0206    2.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710    0.7612    2.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8666    1.0746    1.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0709   -0.0910    2.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7795   -0.9050   -0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0758   -2.0015    0.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1693   -0.8569    1.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0700   -1.5482   -0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7424    1.4828   -1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    0.5783   -2.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3126    2.3956   -2.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6639    1.8201    0.0181 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
  4  5  1  0
  5  6  1  0
  5  7  1  0
  5  8  1  0
  8  9  1  1
  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
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 13 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27  8  1  0
 26 12  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  6
 13 43  1  6
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Amitiza	Kegg
RU-0211	HMDB
0211, SPI	HMDB
Lubiprostone	KEGG
7-[(2R,4AR,5S,7ar)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoate	Generator

Chemical Formula

C₂₀H₃₂F₂O₅

Average Molecular Weight

390.4619

Monoisotopic Molecular Weight

390.221780544

IUPAC Name

7-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid

Traditional Name

lubiprostone

CAS Registry Number

136790-76-6

SMILES

[H][C@@]12CC(=O)[C@@H](CCCCCCC(O)=O)[C@@]1([H])CC[C@@](O)(O2)C(F)(F)CCCC

InChI Identifier

InChI=1S/C20H32F2O5/c1-2-3-11-19(21,22)20(26)12-10-15-14(16(23)13-17(15)27-20)8-6-4-5-7-9-18(24)25/h14-15,17,26H,2-13H2,1H3,(H,24,25)/t14-,15+,17+,20+/m0/s1

InChI Key

WGFOBBZOWHGYQH-DKYLXPRQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Medium-chain fatty acid
Halogenated fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Oxane
Fatty acid
Fluorohydrin
Halohydrin
Hemiacetal
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organohalogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alkyl halide
Alkyl fluoride
Organic oxygen compound
Organofluoride
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

prostanoid (CHEBI:34945 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.026 g/L	Not Available
LogP	4.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.026 g/L	ALOGPS
logP	2.76	ALOGPS
logP	4.56	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	95.6 m³·mol⁻¹	ChemAxon
Polarizability	41.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	227.66	30932474
DeepCCS	[M+Na]+	203.554	30932474
AllCCS	[M+H]+	199.3	32859911
AllCCS	[M+H-H2O]+	196.9	32859911
AllCCS	[M+NH4]+	201.5	32859911
AllCCS	[M+Na]+	202.1	32859911
AllCCS	[M-H]-	198.3	32859911
AllCCS	[M+Na-2H]-	199.5	32859911
AllCCS	[M+HCOO]-	201.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lubiprostone	[H][C@@]12CC(=O)[C@@H](CCCCCCC(O)=O)[C@@]1([H])CC[C@@](O)(O2)C(F)(F)CCCC	3584.3	Standard polar	33892256
Lubiprostone	[H][C@@]12CC(=O)[C@@H](CCCCCCC(O)=O)[C@@]1([H])CC[C@@](O)(O2)C(F)(F)CCCC	2674.3	Standard non polar	33892256
Lubiprostone	[H][C@@]12CC(=O)[C@@H](CCCCCCC(O)=O)[C@@]1([H])CC[C@@](O)(O2)C(F)(F)CCCC	2693.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lubiprostone,1TMS,isomer #1	CCCCC(F)(F)[C@@]1(O)CC[C@@H]2[C@H](CCCCCCC(=O)O[Si](C)(C)C)C(=O)C[C@H]2O1	2625.2	Semi standard non polar	33892256
Lubiprostone,1TMS,isomer #2	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@@H]2[C@H](CCCCCCC(=O)O)C(=O)C[C@H]2O1	2672.4	Semi standard non polar	33892256
Lubiprostone,1TMS,isomer #3	CCCCC(F)(F)[C@@]1(O)CC[C@@H]2C(CCCCCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]2O1	2681.9	Semi standard non polar	33892256
Lubiprostone,1TMS,isomer #4	CCCCC(F)(F)[C@@]1(O)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C)[C@H]2CCCCCCC(=O)O)O1	2615.4	Semi standard non polar	33892256
Lubiprostone,2TMS,isomer #1	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@@H]2[C@H](CCCCCCC(=O)O[Si](C)(C)C)C(=O)C[C@H]2O1	2682.4	Semi standard non polar	33892256
Lubiprostone,2TMS,isomer #2	CCCCC(F)(F)[C@@]1(O)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]2O1	2694.0	Semi standard non polar	33892256
Lubiprostone,2TMS,isomer #3	CCCCC(F)(F)[C@@]1(O)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C)O1	2679.0	Semi standard non polar	33892256
Lubiprostone,2TMS,isomer #4	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]2O1	2743.4	Semi standard non polar	33892256
Lubiprostone,2TMS,isomer #5	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C)[C@H]2CCCCCCC(=O)O)O1	2679.7	Semi standard non polar	33892256
Lubiprostone,3TMS,isomer #1	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]2O1	2736.0	Semi standard non polar	33892256
Lubiprostone,3TMS,isomer #1	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]2O1	2843.1	Standard non polar	33892256
Lubiprostone,3TMS,isomer #1	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]2O1	2874.2	Standard polar	33892256
Lubiprostone,3TMS,isomer #2	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C)O1	2728.7	Semi standard non polar	33892256
Lubiprostone,3TMS,isomer #2	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C)O1	2781.2	Standard non polar	33892256
Lubiprostone,3TMS,isomer #2	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C)O1	2897.3	Standard polar	33892256
Lubiprostone,1TBDMS,isomer #1	CCCCC(F)(F)[C@@]1(O)CC[C@@H]2[C@H](CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)C[C@H]2O1	2863.8	Semi standard non polar	33892256
Lubiprostone,1TBDMS,isomer #2	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@@H]2[C@H](CCCCCCC(=O)O)C(=O)C[C@H]2O1	2897.6	Semi standard non polar	33892256
Lubiprostone,1TBDMS,isomer #3	CCCCC(F)(F)[C@@]1(O)CC[C@@H]2C(CCCCCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]2O1	2896.1	Semi standard non polar	33892256
Lubiprostone,1TBDMS,isomer #4	CCCCC(F)(F)[C@@]1(O)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H]2CCCCCCC(=O)O)O1	2838.7	Semi standard non polar	33892256
Lubiprostone,2TBDMS,isomer #1	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@@H]2[C@H](CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)C[C@H]2O1	3163.5	Semi standard non polar	33892256
Lubiprostone,2TBDMS,isomer #2	CCCCC(F)(F)[C@@]1(O)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]2O1	3146.3	Semi standard non polar	33892256
Lubiprostone,2TBDMS,isomer #3	CCCCC(F)(F)[C@@]1(O)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O1	3137.0	Semi standard non polar	33892256
Lubiprostone,2TBDMS,isomer #4	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]2O1	3176.5	Semi standard non polar	33892256
Lubiprostone,2TBDMS,isomer #5	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H]2CCCCCCC(=O)O)O1	3137.6	Semi standard non polar	33892256
Lubiprostone,3TBDMS,isomer #1	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]2O1	3407.7	Semi standard non polar	33892256
Lubiprostone,3TBDMS,isomer #1	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]2O1	3278.1	Standard non polar	33892256
Lubiprostone,3TBDMS,isomer #1	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]2O1	3119.2	Standard polar	33892256
Lubiprostone,3TBDMS,isomer #2	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O1	3398.9	Semi standard non polar	33892256
Lubiprostone,3TBDMS,isomer #2	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O1	3120.6	Standard non polar	33892256
Lubiprostone,3TBDMS,isomer #2	CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O1	3109.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lubiprostone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-5294000000-b83d3a55a0ca5eba6c03	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lubiprostone GC-MS (2 TMS) - 70eV, Positive	splash10-06di-9647460000-b581533fe4735515641f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lubiprostone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lubiprostone 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 - Lubiprostone 10V, Positive-QTOF	splash10-05fr-0392000000-baf7c2f7194ed88b0807	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lubiprostone 20V, Positive-QTOF	splash10-05fr-1893000000-05146ad09171774b81e0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lubiprostone 40V, Positive-QTOF	splash10-07vl-9300000000-1a9036825efee41873b9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lubiprostone 10V, Negative-QTOF	splash10-000i-0098000000-cf19376ddba1a5e460da	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lubiprostone 20V, Negative-QTOF	splash10-007a-1259000000-85786687d62231129447	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lubiprostone 40V, Negative-QTOF	splash10-0a4i-7890000000-6c74f2fbdce947cdac53	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lubiprostone 10V, Positive-QTOF	splash10-05fr-0009000000-35b5046ad072d78455ad	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lubiprostone 20V, Positive-QTOF	splash10-0avm-2039000000-2b4a8e65036c57034fc4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lubiprostone 40V, Positive-QTOF	splash10-0aor-9520000000-990c2c5e8a719726e6c9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lubiprostone 10V, Negative-QTOF	splash10-000i-0009000000-a5d6e24227bc8251fbe7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lubiprostone 20V, Negative-QTOF	splash10-000i-0029000000-bb4185547119f78da3db	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lubiprostone 40V, Negative-QTOF	splash10-00kr-0193000000-9320001baca5e457ccf2	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01046	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01046	21059682	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

571057

KEGG Compound ID

C13707

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lubiprostone

METLIN ID

Not Available

PubChem Compound

656719

PDB ID

Not Available

ChEBI ID

34945

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lacy BE, Chey WD: Lubiprostone: chronic constipation and irritable bowel syndrome with constipation. Expert Opin Pharmacother. 2009 Jan;10(1):143-52. doi: 10.1517/14656560802631319 . [PubMed:19236188 ]
Lacy BE, Levy LC: Lubiprostone: a novel treatment for chronic constipation. Clin Interv Aging. 2008;3(2):357-64. [PubMed:18686757 ]
Crowell MD, Harris LA, DiBaise JK, Olden KW: Activation of type-2 chloride channels: a novel therapeutic target for the treatment of chronic constipation. Curr Opin Investig Drugs. 2007 Jan;8(1):66-70. [PubMed:17263187 ]
Ambizas EM, Ginzburg R: Lubiprostone: a chloride channel activator for treatment of chronic constipation. Ann Pharmacother. 2007 Jun;41(6):957-64. Epub 2007 May 22. [PubMed:17519292 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Carbonyl reductase [NADPH] 1

General function:: Involved in oxidoreductase activity
Specific function:: NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:: CBR1
Uniprot ID:: P16152
Molecular weight:: 30374.73

References

Lacy BE, Chey WD: Lubiprostone: chronic constipation and irritable bowel syndrome with constipation. Expert Opin Pharmacother. 2009 Jan;10(1):143-52. doi: 10.1517/14656560802631319 . [PubMed:19236188 ]
Lacy BE, Levy LC: Lubiprostone: a novel treatment for chronic constipation. Clin Interv Aging. 2008;3(2):357-64. [PubMed:18686757 ]

Enzyme Details

2. Chloride channel protein 2

General function:: Involved in voltage-gated chloride channel activity
Specific function:: Voltage-gated chloride channel. Chloride channels have several functions including the regulation of cell volume; membrane potential stabilization, signal transduction and transepithelial transport
Gene Name:: CLCN2
Uniprot ID:: P51788
Molecular weight:: 98534.4

References

Authors unspecified: Lubiprostone: RU 0211, SPI 0211. Drugs R D. 2005;6(4):245-8. [PubMed:15991886 ]
Moeser AJ, Nighot PK, Engelke KJ, Ueno R, Blikslager AT: Recovery of mucosal barrier function in ischemic porcine ileum and colon is stimulated by a novel agonist of the ClC-2 chloride channel, lubiprostone. Am J Physiol Gastrointest Liver Physiol. 2007 Feb;292(2):G647-56. Epub 2006 Oct 19. [PubMed:17053162 ]
Lacy BE, Levy LC: Lubiprostone: a chloride channel activator. J Clin Gastroenterol. 2007 Apr;41(4):345-51. [PubMed:17413599 ]
Crowell MD, Harris LA, DiBaise JK, Olden KW: Activation of type-2 chloride channels: a novel therapeutic target for the treatment of chronic constipation. Curr Opin Investig Drugs. 2007 Jan;8(1):66-70. [PubMed:17263187 ]
Lacy BE, Chey WD: Lubiprostone: chronic constipation and irritable bowel syndrome with constipation. Expert Opin Pharmacother. 2009 Jan;10(1):143-52. doi: 10.1517/14656560802631319 . [PubMed:19236188 ]
Ambizas EM, Ginzburg R: Lubiprostone: a chloride channel activator for treatment of chronic constipation. Ann Pharmacother. 2007 Jun;41(6):957-64. Epub 2007 May 22. [PubMed:17519292 ]
Lacy BE, Levy LC: Lubiprostone: a novel treatment for chronic constipation. Clin Interv Aging. 2008;3(2):357-64. [PubMed:18686757 ]
Johanson JF, Ueno R: Lubiprostone, a locally acting chloride channel activator, in adult patients with chronic constipation: a double-blind, placebo-controlled, dose-ranging study to evaluate efficacy and safety. Aliment Pharmacol Ther. 2007 Jun 1;25(11):1351-61. [PubMed:17509103 ]
Kapoor S: Emerging new therapeutic options for the management of opioid induced constipation. J Pain Palliat Care Pharmacother. 2010 Mar;24(1):98-9. doi: 10.3109/15360280903475593. [PubMed:20345211 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Lubiprostone (HMDB0015180)

MOL for HMDB0015180 (Lubiprostone)

3D MOL for HMDB0015180 (Lubiprostone)

3D SDF for HMDB0015180 (Lubiprostone)

3D-SDF for HMDB0015180 (Lubiprostone)

PDB for HMDB0015180 (Lubiprostone)

3D PDB for HMDB0015180 (Lubiprostone)

SMILES for HMDB0015180 (Lubiprostone)

INCHI for HMDB0015180 (Lubiprostone)

Structure for HMDB0015180 (Lubiprostone)

3D Structure for HMDB0015180 (Lubiprostone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References