CAS 82079-32-1|(5R)-4-hydroxy-3,5-dimethyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-2,5-dihydrothiophen-2-one|thiolactomycin|4-Hydroxy-3,5-Dimethyl-5-(2-Methyl-Buta-1,3-Dienyl)-5h-Thiophen-2-One|(5R)-4-H...

General Information

Structure

Molecular Formula

C₁₁H₁₄O₂S

Molecular Mass

210.29266

Exact Mass

210.07145069

Charge

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

Canonic Smiles

C=C/C(=C/[C@@]1(C)SC(=O)C(=C1O)C)/C

Isomeric Smiles

S1C(=O)C(=C([C@]1(/C=C(/C=C)\C)C)O)C

Calculated Properties

JChem

Acid pKa

6.8191414

H Acceptors

H Donor

LogD (pH = 5.5)

2.5264478

LogD (pH = 7.4)

1.8651812

Log P

2.5467854

Molar Refractivity

62.0118

Polarizability

23.335169

Polar Surface Area

37.3

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

2.14

LOG S

-2.62

Solubility (Water)

4.99e-01 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC Traditional name

thiolactomycin (5R)-4-hydroxy-3,5-dimethyl-5-(2-methylbuta-1,3-dien-1-yl)thiophen-2-one

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

Synonyms

4-Hydroxy-3,5-Dimethyl-5-(2-Methyl-Buta-1,3-Dienyl)-5h-Thiophen-2-OneAntibiotic 2-200(5R)-4-Hydroxy-3,5-dimethyl-5-[(1E)-2-methyl-1,3-butadienyl]-2(5H)-thiophenoneThiolactomycin[R-(E)]-4-Hydroxy-3,5-dimethyl-5-(2-methyl-1,3-butadienyl)-2(5H)-thiophenone

Names and Identifiers

Registration numbers

PubChem SID

2427863146505720160967345

MDL Number

MFCD01940028

CAS Number

82079-32-1

PubChem CID

445629

Registration numbers

Properties

Physical Property

Apperance

light yellow solid

Solubility

H2O: insoluble

DMSO: soluble ~21 mg/mL

Safety Information

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

German water hazard class

MSDS Link

Download link

RTECS

XN1928870

Pharmacology Properties

Gene Information

human ... FASN(2194)

Product Information

Empirical Formula (Hill Notation)

C11H14O2S

Purity

98% (HPLC)

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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.

Molecule Details

References

PubChem Literature

No Data Available

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References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

IUPAC Traditional name

thiolactomycin (5R)-4-hydroxy-3,5-dimethyl-5-(2-methylbuta-1,3-dien-1-yl)thiophen-2-one

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

Synonyms

Registration numbers

PubChem SID

2427863146505720160967345

MDL Number

MFCD01940028

CAS Number

82079-32-1

PubChem CID

445629

Properties

Physical Property