Chemical Components in the PDB

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27H : Summary

Code

27H

One-letter code

X

Molecule name

ferutinine

Synonyms

(3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate

Systematic names

ProgramVersionName
ACDLabs 12.01 (3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate
OpenEye OEToolkits 1.7.6 [(3R,3aS,4S,8aR)-6,8a-dimethyl-3-oxidanyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] 4-oxidanylbenzoate

Formula

C22 H30 O4

Formal charge

0

Molecular weight

358.471 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 O=C(OC1C2C(CC=C(C)C1)(CCC2(O)C(C)C)C)c3ccc(O)cc3
SMILES CACTVS 3.385 CC(C)[C]1(O)CC[C]2(C)CC=C(C)C[CH](OC(=O)c3ccc(O)cc3)[CH]12
SMILES OpenEye OEToolkits 1.7.6 CC1=CCC2(CCC(C2C(C1)OC(=O)c3ccc(cc3)O)(C(C)C)O)C
Canonical SMILES CACTVS 3.385 CC(C)[C@]1(O)CC[C@]2(C)CC=C(C)C[C@H](OC(=O)c3ccc(O)cc3)[C@@H]12
Canonical SMILES OpenEye OEToolkits 1.7.6 CC1=CC[C@]2(CC[C@]([C@@H]2[C@H](C1)OC(=O)c3ccc(cc3)O)(C(C)C)O)C

IUPAC InChI

InChI=1S/C22H30O4/c1-14(2)22(25)12-11-21(4)10-9-15(3)13-18(19(21)22)26-20(24)16-5-7-17(23)8-6-16/h5-9,14,18-19,23,25H,10-13H2,1-4H3/t18-,19+,21-,22+/m0/s1

IUPAC InChI key

CYSHNJQMYORNJI-YUVXSKOASA-N
27H

wwPDB Information

Atom count

56 (26 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2013-09-05

Last modified at

2020-06-17

Status

Released

Obsoleted

Not Assigned



27H : Atoms of Molecule

Total Number of Atoms: 56
Record Atom Name Symbol PDB Name Stereochemistry Is Aromatic Is Leaving Atom Charge X-Coordinate Y-Coordinate Z-Coordinate
1 CAB C CAB N N N 0 0.198 3.808 0.448
2 CAV C CAV N N N 0 0.537 2.549 -0.352
3 CAC C CAC N N N 0 1.2 2.947 -1.672
4 CAZ C CAZ R N N 0 1.496 1.673 0.457
5 CAX C CAX S N N 0 1.868 0.419 -0.338
6 OAG O OAG N N N 0 0.9 1.31 1.704
7 CAO C CAO N N N 0 2.829 2.421 0.697
8 CAN C CAN N N N 0 3.942 1.552 0.058
9 CAY C CAY R N N 0 3.321 0.144 0.026
10 CAD C CAD N N N 0 3.394 -0.484 1.419
11 CAM C CAM N N N 0 3.975 -0.783 -0.986
12 CAH C CAH N N N 0 3.691 -2.2 -0.528
13 CAR C CAR N N N 0 2.478 -2.677 -0.577
14 CAA C CAA N N N 0 2.217 -4.072 -0.069
15 CAP C CAP N N N 0 1.325 -1.867 -1.132
16 CAW C CAW S N N 0 0.95 -0.759 -0.136
17 OAQ O OAQ N N N 0 -0.424 -0.349 -0.363
18 CAS C CAS N N N 0 -1.38 -1.001 0.327
19 OAE O OAE N N N 0 -1.073 -1.889 1.098
20 CAU C CAU N Y N 0 -2.797 -0.638 0.148
21 CAK C CAK N Y N 0 -3.153 0.38 -0.742
22 CAI C CAI N Y N 0 -4.478 0.715 -0.907
23 CAT C CAT N Y N 0 -5.462 0.045 -0.189
24 OAF O OAF N N N 0 -6.766 0.379 -0.355
25 CAJ C CAJ N Y N 0 -5.113 -0.968 0.697
26 CAL C CAL N Y N 0 -3.79 -1.313 0.864
27 H1 H H1 N N N 0 -0.486 4.431 -0.128
28 H2 H H2 N N N 0 -0.275 3.524 1.389
29 H3 H H3 N N N 0 1.112 4.365 0.654
30 H4 H H4 N N N 0 -0.377 1.992 -0.558
31 H5 H H5 N N N 0 2.171 3.399 -1.469
32 H6 H H6 N N N 0 1.335 2.06 -2.293
33 H7 H H7 N N N 0 0.567 3.663 -2.195
34 H8 H H8 N N N 0 1.851 0.68 -1.396
35 H9 H H9 N N N 0 0.644 2.064 2.252
36 H10 H H10 N N N 0 2.799 3.401 0.22
37 H11 H H11 N N N 0 3.008 2.532 1.766
38 H12 H H12 N N N 0 4.166 1.896 -0.952
39 H13 H H13 N N N 0 4.84 1.561 0.676
40 H14 H H14 N N N 0 2.867 0.15 2.131
41 H15 H H15 N N N 0 2.929 -1.47 1.398
42 H16 H H16 N N N 0 4.437 -0.58 1.72
43 H17 H H17 N N N 0 3.546 -0.618 -1.974
44 H18 H H18 N N N 0 5.05 -0.608 -1.011
45 H19 H H19 N N N 0 4.496 -2.818 -0.16
46 H20 H H20 N N N 0 3.149 -4.508 0.291
47 H21 H H21 N N N 0 1.495 -4.032 0.747
48 H22 H H22 N N N 0 1.818 -4.684 -0.878
49 H23 H H23 N N N 0 1.62 -1.418 -2.081
50 H24 H H24 N N N 0 0.466 -2.519 -1.291
51 H25 H H25 N N N 0 1.056 -1.133 0.882
52 H26 H H26 N N N 0 -2.389 0.901 -1.3
53 H27 H H27 N N N 0 -4.753 1.501 -1.595
54 H28 H H28 N N N 0 -7.214 -0.117 -1.053
55 H29 H H29 N N N 0 -5.88 -1.486 1.253
56 H30 H H30 N N N 0 -3.52 -2.103 1.549



27H : Chemical Bonds

Total Number of Bonds: 58
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 CAD CAY C C sing 1.53 N N
2 CAN CAY C C sing 1.54 N N
3 CAN CAO C C sing 1.55 N N
4 CAM CAY C C sing 1.52 N N
5 CAM CAH C C sing 1.52 N N
6 CAY CAX C C sing 1.52 N N
7 CAH CAR C C doub 1.3 N N
8 CAO CAZ C C sing 1.55 N N
9 OAG CAZ O C sing 1.43 N N
10 CAA CAR C C sing 1.51 N N
11 CAR CAP C C sing 1.51 N N
12 CAZ CAX C C sing 1.53 N N
13 CAZ CAV C C sing 1.53 N N
14 CAX CAW C C sing 1.51 N N
15 CAW CAP C C sing 1.54 N N
16 CAW OAQ C O sing 1.45 N N
17 CAV CAB C C sing 1.53 N N
18 CAV CAC C C sing 1.53 N N
19 OAE CAS O C doub 1.22 N N
20 OAQ CAS O C sing 1.35 N N
21 CAS CAU C C sing 1.47 N N
22 CAU CAL C C doub 1.4 N Y
23 CAU CAK C C sing 1.4 N Y
24 CAL CAJ C C sing 1.38 N Y
25 CAK CAI C C doub 1.38 N Y
26 CAJ CAT C C doub 1.39 N Y
27 CAI CAT C C sing 1.39 N Y
28 CAT OAF C O sing 1.36 N N
29 CAB H1 C H sing 1.09 N N
30 CAB H2 C H sing 1.09 N N
31 CAB H3 C H sing 1.09 N N
32 CAV H4 C H sing 1.09 N N
33 CAC H5 C H sing 1.09 N N
34 CAC H6 C H sing 1.09 N N
35 CAC H7 C H sing 1.09 N N
36 CAX H8 C H sing 1.09 N N
37 OAG H9 O H sing 0.97 N N
38 CAO H10 C H sing 1.09 N N
39 CAO H11 C H sing 1.09 N N
40 CAN H12 C H sing 1.09 N N
41 CAN H13 C H sing 1.09 N N
42 CAD H14 C H sing 1.09 N N
43 CAD H15 C H sing 1.09 N N
44 CAD H16 C H sing 1.09 N N
45 CAM H17 C H sing 1.09 N N
46 CAM H18 C H sing 1.09 N N
47 CAH H19 C H sing 1.08 N N
48 CAA H20 C H sing 1.09 N N
49 CAA H21 C H sing 1.09 N N
50 CAA H22 C H sing 1.09 N N
51 CAP H23 C H sing 1.09 N N
52 CAP H24 C H sing 1.09 N N
53 CAW H25 C H sing 1.09 N N
54 CAK H26 C H sing 1.08 N N
55 CAI H27 C H sing 1.08 N N
56 OAF H28 O H sing 0.97 N N
57 CAJ H29 C H sing 1.08 N N
58 CAL H30 C H sing 1.08 N N



27H : Used in PDB Entries

Total Number of PDB Entries: 2
Ligand Code PDB Entry ID Type Total Distinct
27H 4mg7 Open in New Window Bound ligand 2 1
27H 7axc Open in New Window Bound ligand 1 1