Chemical Components in the PDB

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15M : Summary

Code

15M

One-letter code

X

Molecule name

(5Z)-7-{(1R,2R,3R,5S)-3,5-DIHYDROXY-2-[(1E,3S)-3-HYDROXY-5-PHENYLPENT-1-ENYL]CYCLOPENTYL}-N-ETHYLHEPT-5-ENAMIDE

Synonyms

BIMATOPROST

Systematic names

ProgramVersionName
ACDLabs 10.04 (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
OpenEye OEToolkits 1.5.0 (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenyl-pent-1-enyl]cyclopentyl]-N-ethyl-hept-5-enamide

Formula

C25 H37 N O4

Formal charge

0

Molecular weight

415.566 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 10.04 O=C(NCC)CCC/C=C\CC2C(/C=C/C(O)CCc1ccccc1)C(O)CC2O
SMILES CACTVS 3.341 CCNC(=O)CCCC=CC[CH]1[CH](O)C[CH](O)[CH]1C=C[CH](O)CCc2ccccc2
SMILES OpenEye OEToolkits 1.5.0 CCNC(=O)CCCC=CCC1C(CC(C1C=CC(CCc2ccccc2)O)O)O
Canonical SMILES CACTVS 3.341 CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCc2ccccc2
Canonical SMILES OpenEye OEToolkits 1.5.0 CCNC(=O)CCC\C=C/C[C@H]1[C@H](C[C@H]([C@@H]1\C=C\[C@H](CCc2ccccc2)O)O)O

IUPAC InChI

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

IUPAC InChI key

AQOKCDNYWBIDND-FTOWTWDKSA-N
15M

wwPDB Information

Atom count

67 (30 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2005-12-07

Last modified at

2020-06-17

Status

Released

Obsoleted

Not Assigned



15M : Atoms of Molecule

Total Number of Atoms: 67
Record Atom Name Symbol PDB Name Stereochemistry Is Aromatic Is Leaving Atom Charge X-Coordinate Y-Coordinate Z-Coordinate
1 C1 C C1 N N N 0 5.812 2.43 0.054
2 C2 C C2 N N N 0 4.548 1.718 -0.357
3 C3 C C3 N N N 0 4.844 0.231 -0.562
4 C4 C C4 N N N 0 3.562 -0.492 -0.979
5 C5 C C5 N N N 0 3.853 -1.957 -1.18
6 C6 C C6 N N N 0 3.125 -2.859 -0.571
7 C7 C C7 N N N 0 1.893 -2.444 0.192
8 C8 C C8 R N N 0 0.691 -3.251 -0.302
9 C9 C C9 S N N 0 0.859 -4.733 0.076
10 C10 C C10 N N N 0 -0.33 -5.093 0.989
11 C11 C C11 R N N 0 -1.419 -4.054 0.622
12 C12 C C12 R N N 0 -0.596 -2.761 0.394
13 C13 C C13 N N N 0 -1.35 -1.805 -0.494
14 C14 C C14 N N N 0 -1.643 -0.603 -0.063
15 C15 C C15 S N N 0 -2.397 0.352 -0.951
16 C16 C C16 N N N 0 -3.649 0.845 -0.222
17 C17 C C17 N N N 0 -4.348 1.908 -1.072
18 C18 C C18 N Y N 0 -5.582 2.394 -0.355
19 C19 C C19 N Y N 0 -6.795 1.767 -0.566
20 C20 C C20 N Y N 0 -7.926 2.209 0.096
21 C21 C C21 N Y N 0 -7.844 3.284 0.961
22 C22 C C22 N Y N 0 -6.632 3.914 1.168
23 C23 C C23 N Y N 0 -5.5 3.469 0.51
24 C24 C C24 N N N 0 6.723 5.935 0.894
25 C25 C C25 N N N 0 7.019 4.448 0.689
26 N N N N N N 0 5.791 3.756 0.29
27 O1 O O1 N N N 0 6.847 1.809 0.171
28 O9 O O9 N N N 0 2.09 -4.923 0.776
29 O11 O O11 N N N 0 -2.343 -3.887 1.699
30 O15 O O15 N N N 0 -2.778 -0.316 -2.155
31 H21A H 1H2 N N N 0 3.796 1.835 0.422
32 H22A H 2H2 N N N 0 4.177 2.146 -1.288
33 H31 H 1H3 N N N 0 5.597 0.114 -1.341
34 H32 H 2H3 N N N 0 5.216 -0.197 0.369
35 H41 H 1H4 N N N 0 2.809 -0.375 -0.199
36 H42 H 2H4 N N N 0 3.19 -0.064 -1.91
37 H5 H H5 N N N 0 4.663 -2.262 -1.826
38 H6 H H6 N N N 0 3.406 -3.901 -0.616
39 H71 H 1H7 N N N 0 2.045 -2.631 1.255
40 H72 H 2H7 N N N 0 1.708 -1.382 0.033
41 H8 H H8 N N N 0 0.592 -3.15 -1.383
42 H9 H H9 N N N 0 0.842 -5.351 -0.822
43 H101 H 1H10 N N N 0 -0.681 -6.103 0.778
44 H102 H 2H10 N N N 0 -0.049 -4.997 2.038
45 H11 H H11 N N N 0 -1.939 -4.346 -0.29
46 H12 H H12 N N N 0 -0.357 -2.288 1.347
47 H13 H H13 N N N 0 -1.649 -2.111 -1.485
48 H14 H H14 N N N 0 -1.344 -0.298 0.929
49 H15 H H15 N N N 0 -1.76 1.203 -1.193
50 H161 H 1H16 N N N 0 -4.328 0.007 -0.059
51 H162 H 2H16 N N N 0 -3.366 1.276 0.738
52 H171 H 1H17 N N N 0 -3.67 2.746 -1.236
53 H172 H 2H17 N N N 0 -4.632 1.478 -2.032
54 H19 H H19 N N N 0 -6.859 0.927 -1.242
55 H20 H H20 N N N 0 -8.873 1.716 -0.066
56 H21 H H21 N N N 0 -8.728 3.631 1.476
57 H22 H H22 N N N 0 -6.568 4.754 1.844
58 H23 H H23 N N N 0 -4.553 3.962 0.672
59 H241 H 1H24 N N N 0 7.637 6.45 1.191
60 H242 H 2H24 N N N 0 6.352 6.363 -0.037
61 H243 H 3H24 N N N 0 5.97 6.052 1.673
62 H251 H 1H25 N N N 0 7.772 4.331 -0.09
63 H252 H 2H25 N N N 0 7.391 4.02 1.62
64 H2 H H2 N N N 0 -3.34 -1.06 -1.896
65 HN H HN N N N 0 4.963 4.253 0.196
66 HO9 H HO9 N N N 0 2.148 -5.864 0.99
67 H1 H H1 N N N 0 -2.764 -4.746 1.842



15M : Chemical Bonds

Total Number of Bonds: 68
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 C1 C2 C C sing 1.51 N N
2 C1 N C N sing 1.35 N N
3 C1 O1 C O doub 1.21 N N
4 C2 C3 C C sing 1.53 N N
5 C2 H21A C H sing 1.09 N N
6 C2 H22A C H sing 1.09 N N
7 C3 C4 C C sing 1.53 N N
8 C3 H31 C H sing 1.09 N N
9 C3 H32 C H sing 1.09 N N
10 C4 C5 C C sing 1.51 N N
11 C4 H41 C H sing 1.09 N N
12 C4 H42 C H sing 1.09 N N
13 C5 C6 C C doub 1.31 Z N
14 C5 H5 C H sing 1.08 N N
15 C6 C7 C C sing 1.51 N N
16 C6 H6 C H sing 1.08 N N
17 C7 C8 C C sing 1.53 N N
18 C7 H71 C H sing 1.09 N N
19 C7 H72 C H sing 1.09 N N
20 C8 C9 C C sing 1.54 N N
21 C8 C12 C C sing 1.54 N N
22 C8 H8 C H sing 1.09 N N
23 C9 C10 C C sing 1.54 N N
24 C9 O9 C O sing 1.43 N N
25 C9 H9 C H sing 1.09 N N
26 C10 C11 C C sing 1.55 N N
27 C10 H101 C H sing 1.09 N N
28 C10 H102 C H sing 1.09 N N
29 C11 C12 C C sing 1.55 N N
30 C11 O11 C O sing 1.43 N N
31 C11 H11 C H sing 1.09 N N
32 C12 C13 C C sing 1.51 N N
33 C12 H12 C H sing 1.09 N N
34 C13 C14 C C doub 1.31 E N
35 C13 H13 C H sing 1.08 N N
36 C14 C15 C C sing 1.51 N N
37 C14 H14 C H sing 1.08 N N
38 C15 C16 C C sing 1.53 N N
39 C15 O15 C O sing 1.43 N N
40 C15 H15 C H sing 1.09 N N
41 C16 C17 C C sing 1.53 N N
42 C16 H161 C H sing 1.09 N N
43 C16 H162 C H sing 1.09 N N
44 C17 C18 C C sing 1.51 N N
45 C17 H171 C H sing 1.09 N N
46 C17 H172 C H sing 1.09 N N
47 C18 C19 C C sing 1.38 N Y
48 C18 C23 C C doub 1.38 N Y
49 C19 C20 C C doub 1.38 N Y
50 C19 H19 C H sing 1.08 N N
51 C20 C21 C C sing 1.38 N Y
52 C20 H20 C H sing 1.08 N N
53 C21 C22 C C doub 1.38 N Y
54 C21 H21 C H sing 1.08 N N
55 C22 C23 C C sing 1.38 N Y
56 C22 H22 C H sing 1.08 N N
57 C23 H23 C H sing 1.08 N N
58 C24 C25 C C sing 1.53 N N
59 C24 H241 C H sing 1.09 N N
60 C24 H242 C H sing 1.09 N N
61 C24 H243 C H sing 1.09 N N
62 C25 N C N sing 1.46 N N
63 C25 H251 C H sing 1.09 N N
64 C25 H252 C H sing 1.09 N N
65 N HN N H sing 0.97 N N
66 O9 HO9 O H sing 0.97 N N
67 O11 H1 O H sing 0.97 N N
68 O15 H2 O H sing 0.97 N N



15M : Used in PDB Entries

Total Number of PDB Entries: 1
Ligand Code PDB Entry ID Type Total Distinct
15M 2f38 Open in New Window Bound ligand 1 1