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Chemical substance record

Thiolutin

87-11-6C8H8N2O2S2228.298 g/mol
Organic/Inorganic Small MoleculeChEBI source record

A dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively. It is a potent inhibitor of RNA polymerases, inhibits the angiogenesis of human umbilical vein endothelial cells, and also inhibits JAMM metalloproteases. — ChEBI

Safety references

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Identity & molecular properties

Source-linked values
CAS number87-11-6ChEBI ↗
Molecular formulaC8H8N2O2S2ChEBI ↗
Molar mass228.298 g/molChEBI ↗
Monoisotopic mass228.00272 DaChEBI ↗
Formal charge0ChEBI ↗
ChEBI identifierCHEBI:156450ChEBI ↗

Cross-source molecular data

PubChem
Molar mass228.3 g/molPubChem ↗
Exact mass228.00271985 DaPubChem ↗
Computed XLogP-0.6PubChem ↗
Topological polar surface area (Ų)100PubChem ↗
H-bond donors1PubChem ↗
H-bond acceptors4PubChem ↗
Rotatable bonds1PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

Copy any identifier
thiolutin
N-(4-methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide
MHMRAFONCSQAIA-UHFFFAOYSA-N
CC(=O)Nc1c2sscc-2n(C)c1=O
InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)

Names & synonyms

N-(4-methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology
dithiolopyrrolone antibioticChEBI parent class · 156449 ↗acetamidesChEBI parent class · 22160 ↗
organosulfur compoundorganic heterocyclic compoundorganic molecular entity

Roles recorded in ChEBI

toxinantibacterial agentantineoplastic agentantifungal agentEC 2.7.7.6 (RNA polymerase) inhibitorchelatorprotein synthesis inhibitorangiogenesis inhibitormarine metabolitebacterial metabolite

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass
Equivalent amount
0.00438024 mol

Uses 228.298 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions
C
Carbon · 8 atoms
42.09%
S
Sulfur · 2 atoms
28.09%
O
Oxygen · 2 atoms
14.02%
N
Nitrogen · 2 atoms
12.27%
H
Hydrogen · 8 atoms
3.53%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations
Thiolutin, an inhibitor of HUVEC adhesion to vitronectin, reduces paxillin in HUVECs and suppresses tumor cell-induced angiogenesis. ↗International journal of cancer · 2001 Aug 1 · PMID 11433393
Determination of mRNA half-lives in Candida albicans using thiolutin as a transcription inhibitor. ↗Genome · 2006 Aug · PMID 17036064
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Sources & record history

Checked 27 Sep 2026
EMBL-EBI ChEBI · CHEBI:156450

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

NCBI PubChem · CID 6870 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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