(5R)-4-hydroxy-3,5-dimethyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-2,5-dihydrothiophen-2-one

• ChemBase ID: 3910
• Molecular Formular: C11H14O2S
• Molecular Mass: 210.29266
• Monoisotopic Mass: 210.07145069
• SMILES: S1C(=O)C(=C([C@]1(/C=C(/C=C)\C)C)O)C
• Canonical SMILES: C=C/C(=C/[C@@]1(C)SC(=O)C(=C1O)C)/C
• InChI: InChI=1S/C11H14O2S/c1-5-7(2)6-11(4)9(12)8(3)10(13)14-11/h5-6,12H,1H2,2-4H3/b7-6+/t11-/m1/s1
• InChIKey: SYQNUQSGEWNWKV-XUIVZRPNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-4-hydroxy-3,5-dimethyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-2,5-dihydrothiophen-2-one; (5R)-4-hydroxy-3,5-dimethyl-5-(2-methylbuta-1,3-dien-1-yl)-2,5-dihydrothiophen-2-one
• IUPAC Traditional name: thiolactomycin; (5R)-4-hydroxy-3,5-dimethyl-5-(2-methylbuta-1,3-dien-1-yl)thiophen-2-one
• Synonyms: 4-Hydroxy-3,5-Dimethyl-5-(2-Methyl-Buta-1,3-Dienyl)-5h-Thiophen-2-One; (5R)-4-Hydroxy-3,5-dimethyl-5-[(1E)-2-methyl-1,3-butadienyl]-2(5H)-thiophenone; Antibiotic 2-200; [R-(E)]-4-Hydroxy-3,5-dimethyl-5-(2-methyl-1,3-butadienyl)-2(5H)-thiophenone; Thiolactomycin

Database IDs

• CAS Number: 82079-32-1
• MDL Number: MFCD01940028
• PubChem SID: 24278631; 46505720; 160967345
• PubChem CID: 445629

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.8191414
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.5264478
• LogD (pH = 7.4): 1.8651812
• Log P: 2.5467854
• Molar Refractivity: 62.0118 cm^3
• Polarizability: 23.335169 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.14
• LOG S: -2.62
• Solubility (Water): 4.99e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: soluble ~21 mg/mL; H2O: insoluble
• Apperance: light yellow solid

Safety Information

• RTECS: XN1928870
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... FASN(2194)

Product Information

• Purity: 98% (HPLC)
• Empirical Formula (Hill Notation): C11H14O2S

DETAILS

DrugBank - DB04302

Drug information: experimental

Sigma Aldrich - T9567

Biochem/physiol Actions
Inhibitor of bacterial myristate synthesis. Does not inhibit eukaryotic myristate synthesis; antibiotic; antitrypanosomal. Shown to be effective against human sleeping sickness parasite, Trypanosoma brucei, as well as malaria parasite and toxoplasma.