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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:50 UTC

HMDB ID

HMDB0015041

Secondary Accession Numbers

HMDB15041

Metabolite Identification

Common Name

Bimatoprost

Description

Bimatoprost, also known as lumigan or latisse, 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. Bimatoprost is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

905
  Mrv0541 02231215052D          

 30 31  0  0  1  0            999 V2000
    8.8251    2.3606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5216   -0.5276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4529   -0.6226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040    4.7477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0478    3.6858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6826    1.4354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5964    0.6149    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4896    1.6070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3501    0.2794    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9021    0.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0695    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8819    0.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2410    2.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8819   -0.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1674   -1.0352    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6279    3.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1674   -1.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8433    3.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4529   -2.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2302    3.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4529   -3.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455    3.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1674   -3.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7384   -3.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325    3.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1674   -4.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7384   -4.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4529   -4.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    4.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  1  0  0  0
  9  2  1  1  0  0  0
 15  3  1  6  0  0  0
  4 25  2  0  0  0  0
  5 25  1  0  0  0  0
  5 29  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  1  1  0  0  0
  7  9  1  0  0  0  0
  7 12  1  6  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 16  2  0  0  0  0
 14 15  1  0  0  0  0
 15 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  2  0  0  0  0
 21 24  1  0  0  0  0
 22 25  1  0  0  0  0
 23 26  1  0  0  0  0
 24 27  2  0  0  0  0
 26 28  2  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

HMDB0015041
     RDKit          3D
Bimatoprost
 67 68  0  0  0  0  0  0  0  0999 V2000
   -6.7441   -2.5346    1.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6243   -1.6438    0.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0638   -1.3009   -0.3588 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4799   -0.9436   -1.5623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9443   -0.1340   -2.4436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1443   -1.5097   -1.9810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3529   -0.3132   -2.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2662    0.6903   -1.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7008    0.0095   -0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696    0.3617    0.5210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7660    1.4800    0.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3379    1.0813    0.1704 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0024    0.3771   -1.0794 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0470    0.2235   -1.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0829    1.2180   -1.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9223    2.5647   -1.0926 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1433    3.2655   -1.5863 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6976    2.1225    0.3624 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9879    1.5668    0.8601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2958    0.3439    1.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850   -0.0304    1.6307 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5853   -0.5175    2.9185 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0942   -1.1669    0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4653   -1.6663    1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4390   -0.5539    0.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0274   -0.3400   -0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9131    0.6875   -0.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2328    1.5347    0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6245    1.2910    1.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7370    0.2501    1.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5578   -3.4941    1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7608   -2.0213    1.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2032   -2.5823    2.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9128   -0.7965    1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6025   -2.2351    0.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1736   -0.5804   -0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6399   -2.1073   -1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3980   -2.0966   -2.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9548    0.1723   -3.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3939   -0.6172   -2.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7942    1.6221   -1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3360    0.9079   -1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2451   -0.9207    0.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866   -0.3225    1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669    2.0095    1.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1084    2.2758   -0.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127    0.2688    1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4436   -0.6354   -0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3423   -0.7438   -1.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0984    0.8345   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875    1.2648   -2.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8294    3.1891   -1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7203    2.7638   -2.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4046    2.9910    0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7569    2.3466    1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -0.4374    1.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3270    0.8329    1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6597   -1.5189    2.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3543   -1.9636    0.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0886   -0.7200   -0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4421   -2.0467    2.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7133   -2.4834    0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8151   -0.9550   -1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3904    0.8932   -1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9224    2.3311    0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8730    1.9503    2.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2868    0.0989    2.9251 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 18 12  1  0
 30 25  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  1
 13 48  1  1
 14 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  1
 17 53  1  0
 18 54  1  1
 19 55  1  0
 20 56  1  0
 21 57  1  1
 22 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 27 64  1  0
 28 65  1  0
 29 66  1  0
 30 67  1  0
M  END

905
  Mrv0541 02231215052D          

 30 31  0  0  1  0            999 V2000
    8.8251    2.3606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5216   -0.5276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4529   -0.6226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040    4.7477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0478    3.6858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6826    1.4354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5964    0.6149    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4896    1.6070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3501    0.2794    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9021    0.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0695    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8819    0.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2410    2.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8819   -0.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1674   -1.0352    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6279    3.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1674   -1.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8433    3.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4529   -2.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2302    3.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4529   -3.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455    3.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1674   -3.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7384   -3.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325    3.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1674   -4.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7384   -4.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4529   -4.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    4.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  1  0  0  0
  9  2  1  1  0  0  0
 15  3  1  6  0  0  0
  4 25  2  0  0  0  0
  5 25  1  0  0  0  0
  5 29  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  1  1  0  0  0
  7  9  1  0  0  0  0
  7 12  1  6  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 16  2  0  0  0  0
 14 15  1  0  0  0  0
 15 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  2  0  0  0  0
 21 24  1  0  0  0  0
 22 25  1  0  0  0  0
 23 26  1  0  0  0  0
 24 27  2  0  0  0  0
 26 28  2  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015041

> <DATABASE_NAME>
hmdb

> <SMILES>
CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21+,22+,23-,24+/m0/s1

> <INCHI_KEY>
AQOKCDNYWBIDND-FTOWTWDKSA-N

> <FORMULA>
C25H37NO4

> <MOLECULAR_WEIGHT>
415.5656

> <EXACT_MASS>
415.272258677

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
48.98886311386664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
2.629262466666666

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.850948591893623

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.347020393912285

> <JCHEM_PKA_STRONGEST_BASIC>
-0.23276572028405906

> <JCHEM_POLAR_SURFACE_AREA>
89.78999999999999

> <JCHEM_REFRACTIVITY>
122.8312

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bimatoprost

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015041
     RDKit          3D
Bimatoprost
 67 68  0  0  0  0  0  0  0  0999 V2000
   -6.7441   -2.5346    1.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6243   -1.6438    0.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0638   -1.3009   -0.3588 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4799   -0.9436   -1.5623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9443   -0.1340   -2.4436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1443   -1.5097   -1.9810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3529   -0.3132   -2.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2662    0.6903   -1.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7008    0.0095   -0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696    0.3617    0.5210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7660    1.4800    0.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3379    1.0813    0.1704 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0024    0.3771   -1.0794 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0470    0.2235   -1.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0829    1.2180   -1.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9223    2.5647   -1.0926 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1433    3.2655   -1.5863 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6976    2.1225    0.3624 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9879    1.5668    0.8601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2958    0.3439    1.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850   -0.0304    1.6307 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5853   -0.5175    2.9185 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0942   -1.1669    0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4653   -1.6663    1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4390   -0.5539    0.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0274   -0.3400   -0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9131    0.6875   -0.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2328    1.5347    0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6245    1.2910    1.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7370    0.2501    1.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5578   -3.4941    1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7608   -2.0213    1.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2032   -2.5823    2.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9128   -0.7965    1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6025   -2.2351    0.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1736   -0.5804   -0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6399   -2.1073   -1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3980   -2.0966   -2.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9548    0.1723   -3.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3939   -0.6172   -2.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7942    1.6221   -1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3360    0.9079   -1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2451   -0.9207    0.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866   -0.3225    1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669    2.0095    1.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1084    2.2758   -0.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127    0.2688    1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4436   -0.6354   -0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3423   -0.7438   -1.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0984    0.8345   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875    1.2648   -2.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8294    3.1891   -1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7203    2.7638   -2.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4046    2.9910    0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7569    2.3466    1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -0.4374    1.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3270    0.8329    1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6597   -1.5189    2.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3543   -1.9636    0.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0886   -0.7200   -0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4421   -2.0467    2.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7133   -2.4834    0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8151   -0.9550   -1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3904    0.8932   -1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9224    2.3311    0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8730    1.9503    2.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2868    0.0989    2.9251 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 18 12  1  0
 30 25  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  1
 13 48  1  1
 14 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  1
 17 53  1  0
 18 54  1  1
 19 55  1  0
 20 56  1  0
 21 57  1  1
 22 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 27 64  1  0
 28 65  1  0
 29 66  1  0
 30 67  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 905                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      16.474   4.406   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      15.907  -0.985   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      10.179  -1.162   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.474   8.862   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.689   6.880   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      14.341   2.679   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.180   1.148   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.847   3.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.587   0.522   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.617   1.666   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.196   3.710   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.846   0.378   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.517   5.216   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.846  -1.162   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.512  -1.932   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.372   6.247   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.512  -3.472   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.907   5.771   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.179  -4.242   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.763   6.801   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.179  -5.782   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.298   6.326   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.512  -6.552   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.845  -6.552   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.154   7.356   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.512  -8.092   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.845  -8.092   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.179  -8.862   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.545   7.911   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.080   7.435   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4   25                                                            
CONECT    5   25   29                                                       
CONECT    6    7    8   11                                                  
CONECT    7    6    9   12                                                  
CONECT    8    1    6   10                                                  
CONECT    9    2    7   10                                                  
CONECT   10    8    9                                                       
CONECT   11    6   13                                                       
CONECT   12    7   14                                                       
CONECT   13   11   16                                                       
CONECT   14   12   15                                                       
CONECT   15    3   14   17                                                  
CONECT   16   13   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   23   24                                                  
CONECT   22   20   25                                                       
CONECT   23   21   26                                                       
CONECT   24   21   27                                                       
CONECT   25    4    5   22                                                  
CONECT   26   23   28                                                       
CONECT   27   24   28                                                       
CONECT   28   26   27                                                       
CONECT   29    5   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

COMPND    HMDB0015041
HETATM    1  C1  UNL     1      -6.744  -2.535   1.716  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.624  -1.644   0.797  1.00  0.00           C  
HETATM    3  N1  UNL     1      -7.064  -1.301  -0.359  1.00  0.00           N  
HETATM    4  C3  UNL     1      -6.480  -0.944  -1.562  1.00  0.00           C  
HETATM    5  O1  UNL     1      -6.944  -0.134  -2.444  1.00  0.00           O  
HETATM    6  C4  UNL     1      -5.144  -1.510  -1.981  1.00  0.00           C  
HETATM    7  C5  UNL     1      -4.353  -0.313  -2.518  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.266   0.690  -1.325  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.701   0.010  -0.161  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.670   0.362   0.521  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.766   1.480   0.391  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.338   1.081   0.170  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.002   0.377  -1.079  1.00  0.00           C  
HETATM   14  O2  UNL     1      -1.047   0.223  -1.963  1.00  0.00           O  
HETATM   15  C12 UNL     1       1.083   1.218  -1.767  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.922   2.565  -1.093  1.00  0.00           C  
HETATM   17  O3  UNL     1      -0.143   3.265  -1.586  1.00  0.00           O  
HETATM   18  C14 UNL     1       0.698   2.122   0.362  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.988   1.567   0.860  1.00  0.00           C  
HETATM   20  C16 UNL     1       2.296   0.344   1.129  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.685  -0.030   1.631  1.00  0.00           C  
HETATM   22  O4  UNL     1       3.585  -0.517   2.919  1.00  0.00           O  
HETATM   23  C18 UNL     1       4.094  -1.167   0.683  1.00  0.00           C  
HETATM   24  C19 UNL     1       5.465  -1.666   1.025  1.00  0.00           C  
HETATM   25  C20 UNL     1       6.439  -0.554   0.900  1.00  0.00           C  
HETATM   26  C21 UNL     1       7.027  -0.340  -0.317  1.00  0.00           C  
HETATM   27  C22 UNL     1       7.913   0.688  -0.472  1.00  0.00           C  
HETATM   28  C23 UNL     1       8.233   1.535   0.601  1.00  0.00           C  
HETATM   29  C24 UNL     1       7.625   1.291   1.811  1.00  0.00           C  
HETATM   30  C25 UNL     1       6.737   0.250   1.944  1.00  0.00           C  
HETATM   31  H1  UNL     1      -6.558  -3.494   1.246  1.00  0.00           H  
HETATM   32  H2  UNL     1      -5.761  -2.021   1.862  1.00  0.00           H  
HETATM   33  H3  UNL     1      -7.203  -2.582   2.724  1.00  0.00           H  
HETATM   34  H4  UNL     1      -7.913  -0.796   1.495  1.00  0.00           H  
HETATM   35  H5  UNL     1      -8.602  -2.235   0.746  1.00  0.00           H  
HETATM   36  H6  UNL     1      -8.174  -0.580  -0.706  1.00  0.00           H  
HETATM   37  H7  UNL     1      -4.640  -2.107  -1.274  1.00  0.00           H  
HETATM   38  H8  UNL     1      -5.398  -2.097  -2.912  1.00  0.00           H  
HETATM   39  H9  UNL     1      -4.955   0.172  -3.300  1.00  0.00           H  
HETATM   40  H10 UNL     1      -3.394  -0.617  -2.869  1.00  0.00           H  
HETATM   41  H11 UNL     1      -3.794   1.622  -1.630  1.00  0.00           H  
HETATM   42  H12 UNL     1      -5.336   0.908  -1.104  1.00  0.00           H  
HETATM   43  H13 UNL     1      -4.245  -0.921   0.217  1.00  0.00           H  
HETATM   44  H14 UNL     1      -2.387  -0.323   1.399  1.00  0.00           H  
HETATM   45  H15 UNL     1      -1.767   2.009   1.403  1.00  0.00           H  
HETATM   46  H16 UNL     1      -2.108   2.276  -0.312  1.00  0.00           H  
HETATM   47  H17 UNL     1      -0.213   0.269   1.009  1.00  0.00           H  
HETATM   48  H18 UNL     1       0.444  -0.635  -0.955  1.00  0.00           H  
HETATM   49  H19 UNL     1      -1.342  -0.744  -1.906  1.00  0.00           H  
HETATM   50  H20 UNL     1       2.098   0.834  -1.486  1.00  0.00           H  
HETATM   51  H21 UNL     1       0.987   1.265  -2.845  1.00  0.00           H  
HETATM   52  H22 UNL     1       1.829   3.189  -1.207  1.00  0.00           H  
HETATM   53  H23 UNL     1      -0.720   2.764  -2.191  1.00  0.00           H  
HETATM   54  H24 UNL     1       0.405   2.991   0.936  1.00  0.00           H  
HETATM   55  H25 UNL     1       2.757   2.347   1.017  1.00  0.00           H  
HETATM   56  H26 UNL     1       1.609  -0.437   1.027  1.00  0.00           H  
HETATM   57  H27 UNL     1       4.327   0.833   1.589  1.00  0.00           H  
HETATM   58  H28 UNL     1       3.660  -1.519   2.936  1.00  0.00           H  
HETATM   59  H29 UNL     1       3.354  -1.964   0.740  1.00  0.00           H  
HETATM   60  H30 UNL     1       4.089  -0.720  -0.344  1.00  0.00           H  
HETATM   61  H31 UNL     1       5.442  -2.047   2.062  1.00  0.00           H  
HETATM   62  H32 UNL     1       5.713  -2.483   0.342  1.00  0.00           H  
HETATM   63  H33 UNL     1       6.815  -0.955  -1.170  1.00  0.00           H  
HETATM   64  H34 UNL     1       8.390   0.893  -1.406  1.00  0.00           H  
HETATM   65  H35 UNL     1       8.922   2.331   0.463  1.00  0.00           H  
HETATM   66  H36 UNL     1       7.873   1.950   2.642  1.00  0.00           H  
HETATM   67  H37 UNL     1       6.287   0.099   2.925  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   34   35
CONECT    3    4   36
CONECT    4    5    5    6
CONECT    6    7   37   38
CONECT    7    8   39   40
CONECT    8    9   41   42
CONECT    9   10   10   43
CONECT   10   11   44
CONECT   11   12   45   46
CONECT   12   13   18   47
CONECT   13   14   15   48
CONECT   14   49
CONECT   15   16   50   51
CONECT   16   17   18   52
CONECT   17   53
CONECT   18   19   54
CONECT   19   20   20   55
CONECT   20   21   56
CONECT   21   22   23   57
CONECT   22   58
CONECT   23   24   59   60
CONECT   24   25   61   62
CONECT   25   26   26   30
CONECT   26   27   63
CONECT   27   28   28   64
CONECT   28   29   65
CONECT   29   30   30   66
CONECT   30   67
END

HMDB0015041
     RDKit          3D
Bimatoprost
 67 68  0  0  0  0  0  0  0  0999 V2000
   -6.7441   -2.5346    1.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6243   -1.6438    0.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0638   -1.3009   -0.3588 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4799   -0.9436   -1.5623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9443   -0.1340   -2.4436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1443   -1.5097   -1.9810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3529   -0.3132   -2.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2662    0.6903   -1.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7008    0.0095   -0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696    0.3617    0.5210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7660    1.4800    0.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3379    1.0813    0.1704 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0024    0.3771   -1.0794 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0470    0.2235   -1.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0829    1.2180   -1.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9223    2.5647   -1.0926 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1433    3.2655   -1.5863 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6976    2.1225    0.3624 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9879    1.5668    0.8601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2958    0.3439    1.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850   -0.0304    1.6307 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5853   -0.5175    2.9185 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0942   -1.1669    0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4653   -1.6663    1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4390   -0.5539    0.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0274   -0.3400   -0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9131    0.6875   -0.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2328    1.5347    0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6245    1.2910    1.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7370    0.2501    1.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5578   -3.4941    1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7608   -2.0213    1.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2032   -2.5823    2.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9128   -0.7965    1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6025   -2.2351    0.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1736   -0.5804   -0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6399   -2.1073   -1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3980   -2.0966   -2.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9548    0.1723   -3.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3939   -0.6172   -2.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7942    1.6221   -1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3360    0.9079   -1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2451   -0.9207    0.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866   -0.3225    1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669    2.0095    1.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1084    2.2758   -0.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127    0.2688    1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4436   -0.6354   -0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3423   -0.7438   -1.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0984    0.8345   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875    1.2648   -2.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8294    3.1891   -1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7203    2.7638   -2.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4046    2.9910    0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7569    2.3466    1.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -0.4374    1.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3270    0.8329    1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6597   -1.5189    2.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3543   -1.9636    0.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0886   -0.7200   -0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4421   -2.0467    2.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7133   -2.4834    0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8151   -0.9550   -1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3904    0.8932   -1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9224    2.3311    0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8730    1.9503    2.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2868    0.0989    2.9251 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 18 12  1  0
 30 25  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  1
 13 48  1  1
 14 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  1
 17 53  1  0
 18 54  1  1
 19 55  1  0
 20 56  1  0
 21 57  1  1
 22 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 27 64  1  0
 28 65  1  0
 29 66  1  0
 30 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((1E,3S)-3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-N-ethyl-5-heptenamide	ChEBI
Bimatoprostum	ChEBI
Lumigan	Kegg
Latisse	Kegg
AGN 192024	HMDB

Chemical Formula

C₂₅H₃₇NO₄

Average Molecular Weight

415.5656

Monoisotopic Molecular Weight

415.272258677

IUPAC Name

(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide

Traditional Name

bimatoprost

CAS Registry Number

155206-00-1

SMILES

CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=CC=C1

InChI Identifier

InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21+,22+,23-,24+/m0/s1

InChI Key

AQOKCDNYWBIDND-FTOWTWDKSA-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
Monocyclic benzene moiety
Cyclopentanol
Fatty amide
Benzenoid
N-acyl-amine
Cyclic alcohol
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:51230 )

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	0.019 g/L	Not Available
LogP	3.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	3.41	ALOGPS
logP	2.63	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	14.35	ChemAxon
pKa (Strongest Basic)	-0.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	89.79 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	122.83 m³·mol⁻¹	ChemAxon
Polarizability	48.99 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
DarkChem	[M+H]+	205.238	31661259
DarkChem	[M-H]-	200.987	31661259
DeepCCS	[M+H]+	203.597	30932474
DeepCCS	[M-H]-	201.536	30932474
DeepCCS	[M-2H]-	234.776	30932474
DeepCCS	[M+Na]+	209.51	30932474
AllCCS	[M+H]+	209.7	32859911
AllCCS	[M+H-H2O]+	207.3	32859911
AllCCS	[M+NH4]+	211.9	32859911
AllCCS	[M+Na]+	212.5	32859911
AllCCS	[M-H]-	204.7	32859911
AllCCS	[M+Na-2H]-	206.8	32859911
AllCCS	[M+HCOO]-	209.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bimatoprost	CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=CC=C1	4489.9	Standard polar	33892256
Bimatoprost	CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=CC=C1	3152.6	Standard non polar	33892256
Bimatoprost	CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=CC=C1	3712.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bimatoprost,1TMS,isomer #1	CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1	3436.3	Semi standard non polar	33892256
Bimatoprost,1TMS,isomer #2	CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1	3453.3	Semi standard non polar	33892256
Bimatoprost,1TMS,isomer #3	CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C	3519.5	Semi standard non polar	33892256
Bimatoprost,1TMS,isomer #4	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1)[Si](C)(C)C	3488.5	Semi standard non polar	33892256
Bimatoprost,2TMS,isomer #1	CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1	3385.4	Semi standard non polar	33892256
Bimatoprost,2TMS,isomer #2	CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C	3387.0	Semi standard non polar	33892256
Bimatoprost,2TMS,isomer #3	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1)[Si](C)(C)C	3361.7	Semi standard non polar	33892256
Bimatoprost,2TMS,isomer #4	CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C	3403.4	Semi standard non polar	33892256
Bimatoprost,2TMS,isomer #5	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1)[Si](C)(C)C	3389.2	Semi standard non polar	33892256
Bimatoprost,2TMS,isomer #6	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C)[Si](C)(C)C	3428.9	Semi standard non polar	33892256
Bimatoprost,3TMS,isomer #1	CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C	3362.9	Semi standard non polar	33892256
Bimatoprost,3TMS,isomer #2	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1)[Si](C)(C)C	3304.5	Semi standard non polar	33892256
Bimatoprost,3TMS,isomer #3	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C)[Si](C)(C)C	3321.4	Semi standard non polar	33892256
Bimatoprost,3TMS,isomer #4	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C)[Si](C)(C)C	3334.7	Semi standard non polar	33892256
Bimatoprost,4TMS,isomer #1	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C)[Si](C)(C)C	3294.9	Semi standard non polar	33892256
Bimatoprost,4TMS,isomer #1	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C)[Si](C)(C)C	3230.3	Standard non polar	33892256
Bimatoprost,4TMS,isomer #1	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C)[Si](C)(C)C	3510.0	Standard polar	33892256
Bimatoprost,1TBDMS,isomer #1	CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1	3636.2	Semi standard non polar	33892256
Bimatoprost,1TBDMS,isomer #2	CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1	3648.6	Semi standard non polar	33892256
Bimatoprost,1TBDMS,isomer #3	CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	3734.1	Semi standard non polar	33892256
Bimatoprost,1TBDMS,isomer #4	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3701.7	Semi standard non polar	33892256
Bimatoprost,2TBDMS,isomer #1	CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1	3803.4	Semi standard non polar	33892256
Bimatoprost,2TBDMS,isomer #2	CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	3796.7	Semi standard non polar	33892256
Bimatoprost,2TBDMS,isomer #3	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3821.3	Semi standard non polar	33892256
Bimatoprost,2TBDMS,isomer #4	CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	3798.0	Semi standard non polar	33892256
Bimatoprost,2TBDMS,isomer #5	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3839.5	Semi standard non polar	33892256
Bimatoprost,2TBDMS,isomer #6	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3905.1	Semi standard non polar	33892256
Bimatoprost,3TBDMS,isomer #1	CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	3958.5	Semi standard non polar	33892256
Bimatoprost,3TBDMS,isomer #2	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	4006.1	Semi standard non polar	33892256
Bimatoprost,3TBDMS,isomer #3	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4018.7	Semi standard non polar	33892256
Bimatoprost,3TBDMS,isomer #4	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4016.6	Semi standard non polar	33892256
Bimatoprost,4TBDMS,isomer #1	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4147.0	Semi standard non polar	33892256
Bimatoprost,4TBDMS,isomer #1	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3883.7	Standard non polar	33892256
Bimatoprost,4TBDMS,isomer #1	CCN(C(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3716.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bimatoprost GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2419000000-01cbf5b797f0f438d1a6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bimatoprost GC-MS (3 TMS) - 70eV, Positive	splash10-014i-6231489000-2ec035b55530648dfa88	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bimatoprost 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 - Bimatoprost 10V, Positive-QTOF	splash10-000y-7009100000-04092b804050ddfef5c0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bimatoprost 20V, Positive-QTOF	splash10-0006-9002000000-cd73c6df4099f0d843a7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bimatoprost 40V, Positive-QTOF	splash10-0006-9101000000-16cd33625e643fb8da2b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bimatoprost 10V, Negative-QTOF	splash10-03dj-1009800000-d208fb15379ead12ec34	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bimatoprost 20V, Negative-QTOF	splash10-0295-3009200000-411ffd7d83662240aea7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bimatoprost 40V, Negative-QTOF	splash10-0006-9121000000-1eb5c2b9bed6afaed1ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bimatoprost 10V, Positive-QTOF	splash10-00ls-0009200000-73e1b5344b1922942139	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bimatoprost 20V, Positive-QTOF	splash10-067j-1139100000-af0949d973b14e6f3c11	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bimatoprost 40V, Positive-QTOF	splash10-0006-9711100000-ab9a2b1f75dd718a7e7a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bimatoprost 10V, Negative-QTOF	splash10-03di-0031900000-a254c0c0de4b4706471c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bimatoprost 20V, Negative-QTOF	splash10-03dj-0029300000-f7b4a623bab1403ce58e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bimatoprost 40V, Negative-QTOF	splash10-009x-9367000000-ad7524b223adaec377ff	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 DB00905	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00905	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00905

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4470565

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bimatoprost

METLIN ID

Not Available

PubChem Compound

5311027

PDB ID

15M

ChEBI ID

51230

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

Lim KS, Nau CB, O'Byrne MM, Hodge DO, Toris CB, McLaren JW, Johnson DH: Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study. Ophthalmology. 2008 May;115(5):790-795.e4. doi: 10.1016/j.ophtha.2007.07.002. [PubMed:18452763 ]
Woodward DF, Krauss AH, Chen J, Lai RK, Spada CS, Burk RM, Andrews SW, Shi L, Liang Y, Kedzie KM, Chen R, Gil DW, Kharlamb A, Archeampong A, Ling J, Madhu C, Ni J, Rix P, Usansky J, Usansky H, Weber A, Welty D, Yang W, Tang-Liu DD, Garst ME, Brar B, Wheeler LA, Kaplan LJ: The pharmacology of bimatoprost (Lumigan). Surv Ophthalmol. 2001 May;45 Suppl 4:S337-45. [PubMed:11434936 ]
Brubaker RF: Mechanism of action of bimatoprost (Lumigan). Surv Ophthalmol. 2001 May;45 Suppl 4:S347-51. [PubMed:11434937 ]
Easthope SE, Perry CM: Topical bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension. Drugs Aging. 2002;19(3):231-48. [PubMed:12027782 ]
Christiansen GA, Nau CB, McLaren JW, Johnson DH: Mechanism of ocular hypotensive action of bimatoprost (Lumigan) in patients with ocular hypertension or glaucoma. Ophthalmology. 2004 Sep;111(9):1658-62. [PubMed:15350319 ]
Steinhauser SL: Decreased high-density lipoprotein serum levels associated with topical bimatoprost therapy. Optometry. 2006 Apr;77(4):177-9. [PubMed:16567279 ]
Kruse P, Rieck P, Sherif Z, Liekfeld A: [Cystoid macular edema in a pseudophakic patient after several glaucoma procedures. Is local therapy with bimatoprost the reason?]. Klin Monbl Augenheilkd. 2006 Jun;223(6):534-7. [PubMed:16804825 ]
Chen MJ, Cheng CY, Chen YC, Chou CK, Hsu WM: Effects of bimatoprost 0.03% on ocular hemodynamics in normal tension glaucoma. J Ocul Pharmacol Ther. 2006 Jun;22(3):188-93. [PubMed:16808680 ]
Patil AJ, Vajaranant TS, Edward DP: Bimatoprost - a review. Expert Opin Pharmacother. 2009 Nov;10(16):2759-68. doi: 10.1517/14656560903292649. [PubMed:19874254 ]
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. Aldo-keto reductase family 1 member C3

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:: AKR1C3
Uniprot ID:: P42330
Molecular weight:: 36866.91

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

2. Prostaglandin F2-alpha receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for prostaglandin F2-alpha (PGF2-alpha). The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. Initiates luteolysis in the corpus luteum
Gene Name:: PTGFR
Uniprot ID:: P43088
Molecular weight:: 40054.1

References

Sharif NA, Williams GW, Kelly CR: Bimatoprost and its free acid are prostaglandin FP receptor agonists. Eur J Pharmacol. 2001 Dec 7;432(2-3):211-3. [PubMed:11740958 ]
Sharif NA, Kelly CR, Crider JY: Agonist activity of bimatoprost, travoprost, latanoprost, unoprostone isopropyl ester and other prostaglandin analogs at the cloned human ciliary body FP prostaglandin receptor. J Ocul Pharmacol Ther. 2002 Aug;18(4):313-24. [PubMed:12222762 ]
Sharif NA, Kelly CR, Crider JY, Williams GW, Xu SX: Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells. J Ocul Pharmacol Ther. 2003 Dec;19(6):501-15. [PubMed:14733708 ]
Lim KS, Nau CB, O'Byrne MM, Hodge DO, Toris CB, McLaren JW, Johnson DH: Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study. Ophthalmology. 2008 May;115(5):790-795.e4. doi: 10.1016/j.ophtha.2007.07.002. [PubMed:18452763 ]
Mintz EE: Group supervision: an experiential approach. Int J Group Psychother. 1978 Oct;28(4):467-9. [PubMed:689791 ]
Neacsu AM: [Receptors involved in the mechanism of action of topical prostaglandines]. Oftalmologia. 2009;53(2):3-7. [PubMed:19697832 ]
Wan Z, Woodward DF, Cornell CL, Fliri HG, Martos JL, Pettit SN, Wang JW, Kharlamb AB, Wheeler LA, Garst ME, Landsverk KJ, Struble CS, Stamer WD: Bimatoprost, prostamide activity, and conventional drainage. Invest Ophthalmol Vis Sci. 2007 Sep;48(9):4107-15. [PubMed:17724194 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. Prostaglandin E2 receptor EP1 subtype

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(q) proteins which activate a phosphatidylinositol-calcium second messenger system. May play a role as an important modulator of renal function. Implicated the smooth muscle contractile response to PGE2 in various tissues
Gene Name:: PTGER1
Uniprot ID:: P34995
Molecular weight:: 41800.7

References

Sharif NA, Kelly CR, Crider JY, Williams GW, Xu SX: Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells. J Ocul Pharmacol Ther. 2003 Dec;19(6):501-15. [PubMed:14733708 ]
Ota T, Aihara M, Saeki T, Narumiya S, Araie M: The effects of prostaglandin analogues on prostanoid EP1, EP2, and EP3 receptor-deficient mice. Invest Ophthalmol Vis Sci. 2006 Aug;47(8):3395-9. [PubMed:16877408 ]

Enzyme Details

4. Prostaglandin E2 receptor EP3 subtype

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for prostaglandin E2 (PGE2); the EP3 receptor may be involved in inhibition of gastric acid secretion, modulation of neurotransmitter release in central and peripheral neurons, inhibition of sodium and water reabsorption in kidney tubulus and contraction in uterine smooth muscle. The activity of this receptor can couple to both the inhibition of adenylate cyclase mediated by G-I proteins, and to an elevation of intracellular calcium. The various isoforms have identical ligand binding properties but can interact with different second messenger systems
Gene Name:: PTGER3
Uniprot ID:: P43115
Molecular weight:: 43309.3

References

Sharif NA, Kelly CR, Crider JY, Williams GW, Xu SX: Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells. J Ocul Pharmacol Ther. 2003 Dec;19(6):501-15. [PubMed:14733708 ]
Gabelt BT, Hennes EA, Bendel MA, Constant CE, Okka M, Kaufman PL: Prostaglandin subtype-selective and non-selective IOP-lowering comparison in monkeys. J Ocul Pharmacol Ther. 2009 Feb;25(1):1-8. doi: 10.1089/jop.2008.0089. [PubMed:19232013 ]
Ota T, Aihara M, Saeki T, Narumiya S, Araie M: The effects of prostaglandin analogues on prostanoid EP1, EP2, and EP3 receptor-deficient mice. Invest Ophthalmol Vis Sci. 2006 Aug;47(8):3395-9. [PubMed:16877408 ]

Showing metabocard for Bimatoprost (HMDB0015041)

MOL for HMDB0015041 (Bimatoprost)

3D MOL for HMDB0015041 (Bimatoprost)

3D SDF for HMDB0015041 (Bimatoprost)

3D-SDF for HMDB0015041 (Bimatoprost)

PDB for HMDB0015041 (Bimatoprost)

3D PDB for HMDB0015041 (Bimatoprost)

SMILES for HMDB0015041 (Bimatoprost)

INCHI for HMDB0015041 (Bimatoprost)

Structure for HMDB0015041 (Bimatoprost)

3D Structure for HMDB0015041 (Bimatoprost)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References