Cyclothialidine
AlkaPlorer ID: AK033280
Synonym: None
IUPAC Name: (2S)-2-[[(5R,8S)-8-[[(2S,3R)-1-[(2S)-2-amino-3-hydroxypropanoyl]-3-hydroxypyrrolidine-2-carbonyl]amino]-14,16-dihydroxy-13-methyl-7,11-dioxo-10-oxa-3-thia-6-azabicyclo[10.4.0]hexadeca-1(16),12,14-triene-5-carbonyl]amino]propanoic acid
Structure
SMILES: CC1=C2C(=O)OC[C@H](N=C(O)[C@@H]3[C@H](O)CCN3C(=O)[C@@H](N)CO)C(O)=N[C@H](C(O)=N[C@@H](C)C(=O)O)CSCC2=C(O)C=C1O
InChI: InChI=1S/C26H35N5O12S/c1-10-17(34)5-18(35)12-8-44-9-15(22(37)28-11(2)25(40)41)30-21(36)14(7-43-26(42)19(10)12)29-23(38)20-16(33)3-4-31(20)24(39)13(27)6-32/h5,11,13-16,20,32-35H,3-4,6-9,27H2,1-2H3,(H,28,37)(H,29,38)(H,30,36)(H,40,41)/t11-,13-,14-,15-,16+,20-/m0/s1
InChIKey: HMHQWJDFNVJCHA-BTZKOOKSSA-N
Reference
PubChem CID: 164470
CAS: 147214-63-9
LOTUS: LTS0161384
SuperNatural Ⅲ: SN0129520-03
NPASS: NPC246303
{NPAtlas: NPA007804
Source
Properties Information
Molecule Weight: 641.6560000000002
TPSA？: 288.61999999999995
MolLogP？: -0.8289799999999934
Number of H-Donors: 9
Number of H-Acceptors: 13
RingCount: 3
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Escherichia coli | DNA gyrase | IC50 | 50.0 | nM | 10.1016/j.bmc.2016.04.043 |
| Escherichia coli | Escherichia coli | MIC | 128.0 | ug.mL-1 | 10.1016/j.bmc.2016.04.043 |
| Staphylococcus aureus | DNA gyrase | MNEC | 0.05 | ug ml-1 | 10.1021/jm000017s |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 128.0 | ug.mL-1 | 10.1016/j.bmc.2016.04.043 |
| None | Unchecked | IC50 | 70.0 | nM | 10.1016/j.bmcl.2009.12.060 |