NP-MRD: Showing NP-Card for bimatoprost acid (NP0212479)

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Record Information

Version

2.0

Created at

2022-09-05 11:09:47 UTC

Updated at

2022-09-05 11:09:47 UTC

NP-MRD ID

NP0212479

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bimatoprost acid

Description

17-Phenyl-trinor-prostaglandin F2alpha, also known as 17-phenyl-trinor-PGF2α, 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. Thus, 17-phenyl-trinor-prostaglandin F2ALPHA is considered to be an eicosanoid. bimatoprost acid is found in Trypanosoma brucei. bimatoprost acid was first documented in 2007 (PMID: 17135335). Based on a literature review very few articles have been published on 17-phenyl-trinor-prostaglandin F2alpha.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052213092D          

 28 29  0  0  1  0            999 V2000
    1.2995   -1.0714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0140   -1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0140   -2.3089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7284   -1.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4429   -1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1574   -1.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8718   -1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8718   -2.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1574   -2.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1574   -3.5464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8248   -4.0314    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6094   -3.7764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5699   -4.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7449   -4.8160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2599   -5.4834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899   -4.0314    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7053   -3.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5338   -2.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7492   -2.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1361   -3.2665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776   -1.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7930   -1.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6215   -0.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1631   -0.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3347    0.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2784    0.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0630    0.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2346   -0.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
M  END

     RDKit          3D

 60 61  0  0  0  0  0  0  0  0999 V2000
    7.6760    1.8636    0.3231 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3883    0.6607    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2716   -0.3176    0.5580 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0338    0.3264   -0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0260    0.4638   -1.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7221    0.1856   -2.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1594   -1.1569   -2.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9421   -1.4074   -1.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9145   -0.4601   -1.5358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3287   -0.5714   -0.1814 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2006   -0.2870    0.9789 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4323   -0.8706    0.9955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2242    1.2392    1.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0100    1.7316    0.4071 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2828    2.5864   -0.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2517    0.5096    0.0075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6305    0.1134    1.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427   -0.0791    0.9662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8534   -0.4765    2.0775 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5241    0.3824    3.1523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2797   -0.1537    1.7120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7101   -1.0276    0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1109   -0.6992    0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3226    0.2840   -0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6132    0.6067   -1.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6555   -0.0588   -0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4264   -1.0411    0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1250   -1.3734    0.8468 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8981   -0.7315   -0.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8446   -0.7596   -0.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2909    0.9609    0.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3752    1.5200   -2.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8370   -0.2052   -2.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0484    1.0241   -2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9310    0.3530   -3.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336   -2.0287   -2.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985   -2.4901   -1.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0483   -0.6069   -2.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2331    0.5843   -1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8400   -1.5855   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6293   -0.7057    1.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6713   -1.1862    1.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1135    1.4590    2.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1562    1.6965    0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3446    2.3142    1.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4625    2.6168   -1.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012    0.6163   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2608   -0.0357    2.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2946    0.0801   -0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7207   -1.5292    2.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2721    1.2790    2.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3464    0.9248    1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8902   -0.3126    2.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0846   -0.8625   -0.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6314   -2.0900    0.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4942    0.7915   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8288    1.3815   -1.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6672    0.1820   -0.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2281   -1.5785    0.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9057   -2.1379    1.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 14  1  0
 14 15  1  0
 14 13  1  0
 13 11  1  0
 11 12  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 28 23  1  0
 10 16  1  0
 20 51  1  0
 19 50  1  1
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 24 56  1  0
 25 57  1  0
 26 58  1  0
 27 59  1  0
 28 60  1  0
 18 49  1  0
 17 48  1  0
 16 47  1  6
 14 45  1  1
 15 46  1  0
 13 43  1  0
 13 44  1  0
 11 41  1  1
 12 42  1  0
 10 40  1  1
  9 38  1  0
  9 39  1  0
  8 37  1  0
  7 36  1  0
  6 34  1  0
  6 35  1  0
  5 32  1  0
  5 33  1  0
  4 30  1  0
  4 31  1  0
  3 29  1  0
M  END


  Mrv1652309052213092D          

 28 29  0  0  1  0            999 V2000
    1.2995   -1.0714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0140   -1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0140   -2.3089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7284   -1.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4429   -1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1574   -1.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8718   -1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8718   -2.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1574   -2.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1574   -3.5464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8248   -4.0314    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6094   -3.7764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5699   -4.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7449   -4.8160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2599   -5.4834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899   -4.0314    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7053   -3.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5338   -2.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7492   -2.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1361   -3.2665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776   -1.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7930   -1.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6215   -0.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1631   -0.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3347    0.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2784    0.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0630    0.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2346   -0.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0212479

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,14-15,18-22,24-26H,2,7,10-13,16H2,(H,27,28)/b6-1-,15-14+/t18-,19+,20+,21-,22+/m0/s1

> <INCHI_KEY>
YFHHIZGZVLHBQZ-KDACTHKWSA-N

> <FORMULA>
C23H32O5

> <MOLECULAR_WEIGHT>
388.504

> <EXACT_MASS>
388.22497413

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
43.856708848380364

> <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]hept-5-enoic acid

> <JCHEM_LOGP>
2.8557210599999983

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.361473126073044

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.355293595690585

> <JCHEM_PKA_STRONGEST_BASIC>
-2.846901073097137

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
111.36370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
17-phenyl-trinor-PGF2α

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0       2.426  -2.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.759  -2.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.759  -4.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.093  -2.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.427  -2.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.760  -2.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.094  -2.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.094  -4.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.760  -5.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.760  -6.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.006  -7.525   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.471  -7.049   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.530  -8.990   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.990  -8.990   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.085 -10.236   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.515  -7.525   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.050  -7.049   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.730  -5.543   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.265  -5.067   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.121  -6.098   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.945  -3.561   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.480  -3.085   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.160  -1.578   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.305  -1.103   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.625   0.404   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.520   1.434   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.984   0.958   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.305  -0.548   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

Value	Source
17-Phenyl-trinor-PGF2alpha	ChEBI
9S,11R,15S-Trihydroxy-17-phenyl-18,19,20-trinor-5Z,13E-prostadienoic acid	ChEBI
17-Phenyl-trinor-PGF2a	Generator
17-Phenyl-trinor-PGF2α	Generator
9S,11R,15S-Trihydroxy-17-phenyl-18,19,20-trinor-5Z,13E-prostadienoate	Generator
17-Phenyl-trinor-prostaglandin F2a	Generator
17-Phenyl-trinor-prostaglandin F2α	Generator
17-Phenyl-18,19,20-trinorprostaglandin F2 alpha	MeSH

Chemical Formula

C₂₃H₃₂O₅

Average Mass

388.5040 Da

Monoisotopic Mass

388.22497 Da

IUPAC Name

(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]hept-5-enoic acid

Traditional Name

17-phenyl-trinor-PGF2α

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C23H32O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,14-15,18-22,24-26H,2,7,10-13,16H2,(H,27,28)/b6-1-,15-14+/t18-,19+,20+,21-,22+/m0/s1

InChI Key

YFHHIZGZVLHBQZ-KDACTHKWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trypanosoma brucei	LOTUS Database	35616633

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
Long-chain fatty acid
Hydroxy fatty acid
Monocyclic benzene moiety
Cyclopentanol
Fatty acid
Benzenoid
Unsaturated fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

prostaglandins Falpha (CHEBI:73773 )
Prostaglandins (LMFA03010081 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.86	ChemAxon
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	111.36 m³·mol⁻¹	ChemAxon
Polarizability	43.86 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4446207

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283081

PDB ID

Not Available

ChEBI ID

73773

Good Scents ID

Not Available

References

General References

Cantor LB, Hoop J, Wudunn D, Yung CW, Catoira Y, Valluri S, Cortes A, Acheampong A, Woodward DF, Wheeler LA: Levels of bimatoprost acid in the aqueous humour after bimatoprost treatment of patients with cataract. Br J Ophthalmol. 2007 May;91(5):629-32. doi: 10.1136/bjo.2006.110155. Epub 2006 Nov 29. [PubMed:17135335 ]
LOTUS database [Link]

Showing NP-Card for bimatoprost acid (NP0212479)

MOL for NP0212479 (bimatoprost acid)

3D MOL for NP0212479 (bimatoprost acid)

3D SDF for NP0212479 (bimatoprost acid)

3D-SDF for NP0212479 (bimatoprost acid)

PDB for NP0212479 (bimatoprost acid)

3D PDB for NP0212479 (bimatoprost acid)

SMILES for NP0212479 (bimatoprost acid)

INCHI for NP0212479 (bimatoprost acid)

Structure for NP0212479 (bimatoprost acid)

3D Structure for NP0212479 (bimatoprost acid)