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08Y : Summary

Code

08Y

One-letter code

X

Molecule name

bromoergocryptine

Systematic names

ProgramVersionName
ACDLabs 12.01 (5alpha,5'beta)-2-bromo-12'-hydroxy-5'-(2-methylpropyl)-3',6',18-trioxo-2'-(propan-2-yl)ergotaman

Formula

C32 H40 Br N5 O5

Formal charge

0

Molecular weight

654.594 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 Brc7nc6cccc5C4=CC(C(=O)NC1(OC3(O)N(C1=O)C(C(=O)N2CCCC23)CC(C)C)C(C)C)CN(C)C4Cc7c56
SMILES CACTVS 3.370 CC(C)C[CH]1N2C(=O)[C](NC(=O)[CH]3CN(C)[CH]4Cc5c(Br)[nH]c6cccc(C4=C3)c56)(O[C]2(O)[CH]7CCCN7C1=O)C(C)C
SMILES OpenEye OEToolkits 1.7.2 CC(C)CC1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)C4CN(C5Cc6c7c(cccc7[nH]c6Br)C5=C4)C)O
Canonical SMILES CACTVS 3.370 CC(C)C[C@@H]1N2C(=O)[C@](NC(=O)[C@H]3CN(C)[C@@H]4Cc5c(Br)[nH]c6cccc(C4=C3)c56)(O[C@@]2(O)[C@@H]7CCCN7C1=O)C(C)C
Canonical SMILES OpenEye OEToolkits 1.7.2 CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@H]4CN([C@@H]5Cc6c7c(cccc7[nH]c6Br)C5=C4)C)O

IUPAC InChI

InChI=1S/C32H40BrN5O5/c1-16(2)12-24-29(40)37-11-7-10-25(37)32(42)38(24)30(41)31(43-32,17(3)4)35-28(39)18-13-20-19-8-6-9-22-26(19)21(27(33)34-22)14-23(20)36(5)15-18/h6,8-9,13,16-18,23-25,34,42H,7,10-12,14-15H2,1-5H3,(H,35,39)/t18-,23-,24+,25+,31-,32+/m1/s1

IUPAC InChI key

OZVBMTJYIDMWIL-AYFBDAFISA-N
08Y

wwPDB Information

Atom count

83 (43 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2011-10-31

Last modified at

2021-03-01

Status

Released

Obsoleted

Not Assigned



08Y : Atoms of Molecule

Total Number of Atoms: 83
Record Atom Name Symbol PDB Name Stereochemistry Is Aromatic Is Leaving Atom Charge X-Coordinate Y-Coordinate Z-Coordinate
1 O5 O O5 N N N 0 -0.847 -3.088 -0.374
2 C15 C C15 N N N 0 -0.476 -2.316 0.485
3 C16 C C16 R N N 0 0.996 -2.126 0.743
4 C18 C C18 N N N 0 1.806 -2.996 -0.225
5 N4 N N4 N N N 0 3.23 -2.717 -0.017
6 C27 C C27 N N N 0 4.067 -3.686 -0.737
7 C22 C C22 N N N 0 1.369 -0.686 0.513
8 C21 C C21 N N N 0 2.544 -0.345 0.014
9 C24 C C24 N Y N 0 2.85 1.084 -0.193
10 C30 C C30 N Y N 0 2.006 2.156 -0.371
11 C32 C C32 N Y N 0 2.538 3.43 -0.561
12 C31 C C31 N Y N 0 3.898 3.715 -0.587
13 C28 C C28 N Y N 0 4.782 2.652 -0.407
14 C26 C C26 N Y N 0 4.229 1.384 -0.212
15 C25 C C25 N Y N 0 5.309 0.42 -0.034
16 C23 C C23 N N N 0 4.984 -1.029 0.219
17 C17 C C17 R N N 0 3.6 -1.35 -0.363
18 C29 C C29 N Y N 0 6.429 1.13 -0.138
19 N5 N N5 N Y N 0 6.131 2.466 -0.363
20 BR BR BR N N N 0 8.176 0.421 0.0
21 N3 N N3 N N N 0 -1.382 -1.624 1.205
22 C5 C C5 R N N 0 -2.809 -1.741 0.894
23 O1 O O1 N N N 0 -3.011 -1.637 -0.52
24 C11 C C11 N N N 0 -3.346 -3.079 1.403
25 C14 C C14 N N N 0 -2.671 -4.223 0.643
26 C13 C C13 N N N 0 -3.047 -3.214 2.898
27 C8 C C8 N N N 0 -3.569 -0.604 1.531
28 O3 O O3 N N N 0 -3.599 -0.345 2.716
29 N1 N N1 N N N 0 -4.207 0.071 0.561
30 C3 C C3 S N N 0 -5.166 1.166 0.735
31 C10 C C10 N N N 0 -4.411 2.491 0.86
32 C12 C C12 N N N 0 -5.395 3.607 1.216
33 C20 C C20 N N N 0 -6.009 3.327 2.589
34 C19 C C19 N N N 0 -4.655 4.946 1.252
35 C9 C C9 N N N 0 -6.086 1.224 -0.457
36 O4 O O4 N N N 0 -6.958 2.066 -0.492
37 N2 N N2 N N N 0 -5.962 0.364 -1.483
38 C6 C C6 N N N 0 -6.664 0.444 -2.772
39 C7 C C7 N N N 0 -6.121 -0.693 -3.663
40 C4 C C4 N N N 0 -4.755 -1.031 -3.006
41 C1 C C1 S N N 0 -5.081 -0.822 -1.509
42 C2 C C2 S N N 0 -3.801 -0.471 -0.745
43 O2 O O2 N N N 0 -3.045 0.495 -1.478
44 H1 H H1 N N N 0 1.228 -2.405 1.771
45 H2 H H2 N N N 0 1.606 -4.049 -0.027
46 H3 H H3 N N N 0 1.531 -2.756 -1.252
47 H5 H H5 N N N 0 3.904 -3.582 -1.809
48 H6 H H6 N N N 0 5.117 -3.499 -0.509
49 H7 H H7 N N N 0 3.802 -4.696 -0.425
50 H8 H H8 N N N 0 0.658 0.088 0.761
51 H9 H H9 N N N 0 0.936 2.01 -0.365
52 H10 H H10 N N N 0 1.848 4.25 -0.697
53 H11 H H11 N N N 0 4.256 4.722 -0.742
54 H12 H H12 N N N 0 5.734 -1.658 -0.26
55 H13 H H13 N N N 0 4.981 -1.219 1.292
56 H14 H H14 N N N 0 3.694 -1.311 -1.448
57 H15 H H15 N N N 0 6.791 3.169 -0.473
58 H16 H H16 N N N 0 -1.088 -1.049 1.929
59 H17 H H17 N N N 0 -4.424 -3.123 1.244
60 H18 H H18 N N N 0 -3.186 -5.158 0.861
61 H19 H H19 N N N 0 -2.717 -4.024 -0.428
62 H20 H H20 N N N 0 -1.629 -4.3 0.953
63 H21 H H21 N N N 0 -3.619 -2.47 3.452
64 H22 H H22 N N N 0 -3.325 -4.213 3.236
65 H23 H H23 N N N 0 -1.982 -3.056 3.071
66 H24 H H24 N N N 0 -5.753 0.996 1.638
67 H25 H H25 N N N 0 -3.658 2.407 1.644
68 H26 H H26 N N N 0 -3.925 2.723 -0.087
69 H27 H H27 N N N 0 -6.185 3.648 0.466
70 H28 H H28 N N N 0 -6.76 4.085 2.813
71 H29 H H29 N N N 0 -6.477 2.343 2.584
72 H30 H H30 N N N 0 -5.228 3.354 3.349
73 H31 H H31 N N N 0 -4.218 5.146 0.274
74 H32 H H32 N N N 0 -5.356 5.742 1.506
75 H33 H H33 N N N 0 -3.866 4.905 2.002
76 H34 H H34 N N N 0 -7.736 0.316 -2.619
77 H35 H H35 N N N 0 -6.47 1.41 -3.24
78 H36 H H36 N N N 0 -6.787 -1.556 -3.635
79 H37 H H37 N N N 0 -5.984 -0.347 -4.688
80 H38 H H38 N N N 0 -4.471 -2.065 -3.204
81 H39 H H39 N N N 0 -3.979 -0.342 -3.339
82 H40 H H40 N N N 0 -5.578 -1.695 -1.087
83 H41 H H41 N N N 0 -2.232 0.777 -1.036



08Y : Chemical Bonds

Total Number of Bonds: 89
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 C27 N4 C N sing 1.47 N N
2 BR C29 BR C sing 1.89 N N
3 N4 C18 N C sing 1.47 N N
4 N4 C17 N C sing 1.46 N N
5 C23 C17 C C sing 1.54 N N
6 C23 C25 C C sing 1.51 N N
7 C18 C16 C C sing 1.53 N N
8 C17 C21 C C sing 1.51 N N
9 C29 C25 C C doub 1.33 N Y
10 C29 N5 C N sing 1.39 N Y
11 C13 C11 C C sing 1.53 N N
12 C25 C26 C C sing 1.46 N Y
13 C16 C22 C C sing 1.51 N N
14 C16 C15 C C sing 1.51 N N
15 N5 C28 N C sing 1.36 N Y
16 N3 C15 N C sing 1.35 N N
17 N3 C5 N C sing 1.47 N N
18 C14 C11 C C sing 1.53 N N
19 C21 C22 C C doub 1.32 N N
20 C21 C24 C C sing 1.48 N N
21 C11 C5 C C sing 1.53 N N
22 C26 C28 C C doub 1.4 N Y
23 C26 C24 C C sing 1.41 N Y
24 C15 O5 C O doub 1.21 N N
25 O1 C5 O C sing 1.43 N N
26 O1 C2 O C sing 1.43 N N
27 C5 C8 C C sing 1.51 N N
28 C28 C31 C C sing 1.39 N Y
29 C24 C30 C C doub 1.38 N Y
30 C4 C7 C C sing 1.55 N N
31 C4 C1 C C sing 1.55 N N
32 C2 C1 C C sing 1.53 N N
33 C2 O2 C O sing 1.43 N N
34 C2 N1 C N sing 1.47 N N
35 C7 C6 C C sing 1.54 N N
36 C1 N2 C N sing 1.48 N N
37 C8 O3 C O doub 1.21 N N
38 C8 N1 C N sing 1.34 N N
39 C31 C32 C C doub 1.39 N Y
40 C30 C32 C C sing 1.39 N Y
41 N1 C3 N C sing 1.47 N N
42 N2 C6 N C sing 1.47 N N
43 N2 C9 N C sing 1.34 N N
44 C3 C9 C C sing 1.51 N N
45 C3 C10 C C sing 1.53 N N
46 C9 O4 C O doub 1.21 N N
47 C10 C12 C C sing 1.53 N N
48 C19 C12 C C sing 1.53 N N
49 C12 C20 C C sing 1.53 N N
50 C16 H1 C H sing 1.09 N N
51 C18 H2 C H sing 1.09 N N
52 C18 H3 C H sing 1.09 N N
53 C27 H5 C H sing 1.09 N N
54 C27 H6 C H sing 1.09 N N
55 C27 H7 C H sing 1.09 N N
56 C22 H8 C H sing 1.08 N N
57 C30 H9 C H sing 1.08 N N
58 C32 H10 C H sing 1.08 N N
59 C31 H11 C H sing 1.08 N N
60 C23 H12 C H sing 1.09 N N
61 C23 H13 C H sing 1.09 N N
62 C17 H14 C H sing 1.09 N N
63 N5 H15 N H sing 0.97 N N
64 N3 H16 N H sing 0.97 N N
65 C11 H17 C H sing 1.09 N N
66 C14 H18 C H sing 1.09 N N
67 C14 H19 C H sing 1.09 N N
68 C14 H20 C H sing 1.09 N N
69 C13 H21 C H sing 1.09 N N
70 C13 H22 C H sing 1.09 N N
71 C13 H23 C H sing 1.09 N N
72 C3 H24 C H sing 1.09 N N
73 C10 H25 C H sing 1.09 N N
74 C10 H26 C H sing 1.09 N N
75 C12 H27 C H sing 1.09 N N
76 C20 H28 C H sing 1.09 N N
77 C20 H29 C H sing 1.09 N N
78 C20 H30 C H sing 1.09 N N
79 C19 H31 C H sing 1.09 N N
80 C19 H32 C H sing 1.09 N N
81 C19 H33 C H sing 1.09 N N
82 C6 H34 C H sing 1.09 N N
83 C6 H35 C H sing 1.09 N N
84 C7 H36 C H sing 1.09 N N
85 C7 H37 C H sing 1.09 N N
86 C4 H38 C H sing 1.09 N N
87 C4 H39 C H sing 1.09 N N
88 C1 H40 C H sing 1.09 N N
89 O2 H41 O H sing 0.97 N N



08Y : Used in PDB Entries

Total Number of PDB Entries: 4
Ligand Code PDB Entry ID Type Total Distinct
08Y 3ua1 Open in New Window Bound ligand 1 1
08Y 5vcg Open in New Window Bound ligand 1 1
08Y 6vms Open in New Window Bound ligand 1 1
08Y 7jvr Open in New Window Bound ligand 1 1