Chemical Components in the PDB

pdbe.org/chem
spacer

GA3 : Summary

Code

GA3

One-letter code

X

Molecule name

GIBBERELLIN A3

Synonyms

(1S,2S,4aR,4bR,7S,9aS,10S,10aR)-2,7-dihydroxy-1-methyl-8-methylidene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epo xymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid

Systematic names

ProgramVersionName
ACDLabs 10.04 (1S,2S,4aR,4bR,7S,9aS,10S,10aR)-2,7-dihydroxy-1-methyl-8-methylidene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid

Formula

C19 H22 O6

Formal charge

0

Molecular weight

346.374 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 10.04 O=C(O)C5C21CC(O)(\C(=C)C1)CCC2C34OC(=O)C(C)(C(O)C=C3)C45
SMILES CACTVS 3.341 C[C]12[CH](O)C=C[C]3(OC1=O)[CH]4CC[C]5(O)C[C]4(CC5=C)[CH]([CH]23)C(O)=O
SMILES OpenEye OEToolkits 1.5.0 CC12C(C=CC3(C1C(C45C3CCC(C4)(C(=C)C5)O)C(=O)O)OC2=O)O
Canonical SMILES CACTVS 3.341 C[C@]12[C@@H](O)C=C[C@@]3(OC1=O)[C@@H]4CC[C@]5(O)C[C@]4(CC5=C)[C@H]([C@H]23)C(O)=O
Canonical SMILES OpenEye OEToolkits 1.5.0 C[C@@]12[C@H](C=C[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@](C4)(C(=C)C5)O)C(=O)O)OC2=O)O

IUPAC InChI

InChI=1S/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16-,17+,18+,19-/m1/s1

IUPAC InChI key

IXORZMNAPKEEDV-OBDJNFEBSA-N
GA3

wwPDB Information

Atom count

47 (25 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2008-09-04

Last modified at

2020-06-17

Status

Released

Obsoleted

Not Assigned



GA3 : Atoms of Molecule

Total Number of Atoms: 47
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 1.68 -1.578 1.677
2 C10 C C10 R N N 0 0.735 -0.963 0.705
3 C11 C C11 N N N 0 -1.641 -1.687 1.44
4 C12 C C12 N N N 0 -2.718 -1.994 0.424
5 C13 C C13 S N N 0 -3.058 -0.812 -0.48
6 C14 C C14 N N N 0 -1.718 -0.378 -1.138
7 C15 C C15 N N N 0 -2.247 1.235 0.595
8 C16 C C16 N N N 0 -3.491 0.391 0.337
9 C17 C C17 N N N 0 -4.708 0.656 0.744
10 C18 C C18 N N N 0 2.964 1.075 -1.506
11 C19 C C19 N N N 0 1.814 -1.192 -1.306
12 C2 C C2 N N N 0 2.966 -1.388 1.484
13 C3 C C3 S N N 0 3.542 -0.576 0.361
14 C4 C C4 S N N 0 2.448 -0.023 -0.573
15 C5 C C5 R N N 0 1.319 0.463 0.364
16 C6 C C6 S N N 0 0.157 1.136 -0.388
17 C7 C C7 N N N 0 0.063 2.591 -0.0050
18 C8 C C8 S N N 0 -1.101 0.395 0.049
19 C9 C C9 R N N 0 -0.664 -0.621 1.121
20 H1 H H1 N N N 0 1.321 -2.161 2.513
21 H11 H H11 N N N 0 -2.133 -1.418 2.374
22 H11A H H11A N N N 0 -1.082 -2.606 1.618
23 H12 H H12 N N N 0 -3.621 -2.298 0.955
24 H12A H H12A N N N 0 -2.386 -2.825 -0.197
25 H14 H H14 N N N 0 -1.887 0.275 -1.995
26 H14A H H14A N N N 0 -1.11 -1.24 -1.412
27 H15 H H15 N N N 0 -2.119 1.406 1.664
28 H15A H H15A N N N 0 -2.312 2.183 0.061
29 H17 H H17 N N N 0 -4.902 1.547 1.323
30 H17A H H17A N N N 0 -5.517 -0.016 0.5
31 H18 H H18 N N N 0 3.358 1.9 -0.913
32 H18A H H18A N N N 0 3.755 0.672 -2.139
33 H18B H H18B N N N 0 2.146 1.434 -2.131
34 H2 H H2 N N N 0 3.654 -1.848 2.178
35 H3 H H3 N N N 0 4.218 -1.203 -0.22
36 H5 H H5 N N N 0 1.663 1.028 1.231
37 H6 H H6 N N N 0 0.298 1.039 -1.464
38 H9 H H9 N N N 0 -0.547 -0.038 2.035
39 HO13 H HO13 N N N 0 -4.896 -1.399 -1.094
40 HO31 H HO31 N N N 0 5.013 0.251 1.48
41 HO71 H HO71 N N N 0 -0.367 4.421 -0.623
42 O13 O O13 N N N 0 -4.037 -1.154 -1.463
43 O31 O O31 N N N 0 4.279 0.518 0.91
44 O71 O O71 N N N 0 -0.321 3.501 -0.915
45 O72 O O72 N N N 0 0.333 2.938 1.12
46 O91 O O91 N N N 0 2.164 -1.622 -2.379
47 O92 O O92 N N N 0 0.799 -1.671 -0.565



GA3 : Chemical Bonds

Total Number of Bonds: 51
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 O71 C7 O C sing 1.34 N N
2 C7 O72 C O doub 1.21 N N
3 C7 C6 C C sing 1.51 N N
4 C6 C5 C C sing 1.54 N N
5 C6 C8 C C sing 1.52 N N
6 C5 C10 C C sing 1.58 N N
7 C5 C4 C C sing 1.55 N N
8 C8 C15 C C sing 1.52 N N
9 C8 C14 C C sing 1.55 N N
10 C8 C9 C C sing 1.54 N N
11 C15 C16 C C sing 1.53 N N
12 C16 C17 C C doub 1.31 N N
13 C16 C13 C C sing 1.52 N N
14 C13 C14 C C sing 1.55 N N
15 C13 O13 C O sing 1.43 N N
16 C13 C12 C C sing 1.53 N N
17 C12 C11 C C sing 1.51 N N
18 C11 C9 C C sing 1.48 N N
19 C9 C10 C C sing 1.5 N N
20 C10 O92 C O sing 1.46 N N
21 C10 C1 C C sing 1.49 N N
22 O92 C19 O C sing 1.34 N N
23 C1 C2 C C doub 1.31 N N
24 C2 C3 C C sing 1.5 N N
25 C3 O31 C O sing 1.43 N N
26 C3 C4 C C sing 1.54 N N
27 C4 C18 C C sing 1.53 N N
28 C4 C19 C C sing 1.52 N N
29 C19 O91 C O doub 1.21 N N
30 O71 HO71 O H sing 0.97 N N
31 C6 H6 C H sing 1.09 N N
32 C5 H5 C H sing 1.09 N N
33 C15 H15 C H sing 1.09 N N
34 C15 H15A C H sing 1.09 N N
35 C17 H17 C H sing 1.08 N N
36 C17 H17A C H sing 1.08 N N
37 C14 H14 C H sing 1.09 N N
38 C14 H14A C H sing 1.09 N N
39 O13 HO13 O H sing 0.97 N N
40 C12 H12 C H sing 1.09 N N
41 C12 H12A C H sing 1.09 N N
42 C11 H11 C H sing 1.09 N N
43 C11 H11A C H sing 1.09 N N
44 C9 H9 C H sing 1.09 N N
45 C1 H1 C H sing 1.08 N N
46 C2 H2 C H sing 1.08 N N
47 C3 H3 C H sing 1.09 N N
48 O31 HO31 O H sing 0.97 N N
49 C18 H18 C H sing 1.09 N N
50 C18 H18A C H sing 1.09 N N
51 C18 H18B C H sing 1.09 N N



GA3 : Used in PDB Entries

Total Number of PDB Entries: 4
Ligand Code PDB Entry ID Type Total Distinct
GA3 2zsh Open in New Window Bound ligand 1 1
GA3 3ed1 Open in New Window Bound ligand 6 1
GA3 4psb Open in New Window Bound ligand 1 1
GA3 4q0k Open in New Window Bound ligand 1 1