2,5-Dihydroxy-3,6-bis(4-hydroxyphenyl)-2,5-cyclohexadiene-1,4-dione
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Basic information
- CAS
519-67-5- Standard SMILES
O=C1C(O)=C(c2ccc(O)cc2)C(=O)C(O)=C1c1ccc(O)cc1- InChIKey
FKQQKMGWCJGUCS-UHFFFAOYSA-N- Molecular formula
- C18H12O6
- Average molar mass
- 324.3 g/mol
- Monoisotopic mass
- 324.0633881
Overview
Atromentin is a member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxycyclohexa-2,5-diene-1,4-dione which is substituted by a 4-hydroxyphenyl group at positions 3 and 6. It is a mushroom pigment isolated from several fungi species and acts as a smooth muscle stimulant, and exhibits anticoagulant, antibacterial and antineoplastic properties. It has a role as an EC 1.3.1.9 [enoyl-[acyl-carrier-protein] reductase (NADH)] inhibitor, a biological pigment, an antibacterial agent, an antineoplastic agent, an anticoagulant, an apoptosis inducer and a fungal metabolite. It is a member of dihydroxy-1,4-benzoquinones and a polyphenol. It is a conjugate acid of an atromentin(1-).
Names & identifiers
- Preferred name
- 2,5-Dihydroxy-3,6-bis(4-hydroxyphenyl)-2,5-cyclohexadiene-1,4-dione
- IUPAC
- 2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione
- English name
- 2,5-Dihydroxy-3,6-bis(4-hydroxyphenyl)-2,5-cyclohexadiene-1,4-dione
- Molecular formula
- C18H12O6
- Molecular weight
- 324.28
Names & synonyms
Atromentin519-67-52,5-dihydroxy-3,6-bis(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)-1,4-benzoquinoneNSC-1877302,5-DIHYDROXY-3,6-BIS(4-HYDROXYPHENYL)-2,5-CYCLOHEXADIENE-1,4-DIONEp-Benzoquinone, 2,5-dihydroxy-3,6-bis(p-hydroxyphenyl)-CHEBI:149660DTXSID601998632,5-Cyclohexadiene-1,4-dione, 2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)-59557692U6RefChem:115520
Show more names
NSC187730
DTXCID20122354CHEMBL4593579NSC 187730orb1986485SCHEMBL9176577FKQQKMGWCJGUCS-UHFFFAOYSA-NGLXC-20759BDBM50536674
Database identifiers
- CAS
519-67-5- PubChem CID
- 99148
- DTXSID
DTXSID60199863- ChEMBL
CHEMBL4593579
Properties
Computed structural propertiesFilling in
- XLogP
- 2.3
- Topological polar surface area
- 115 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 547
Physicochemical properties
- Boiling point
- 651.3 · 651.3±55.0 °C(Predicted)
- Density
- 1.644 · 1.644±0.06 g/cm3(Predicted)
- pka
- 2.47 · 2.47±0.50(Predicted)
- FDA UNII
- 59557692 U6 · 59557692U6
Chemistry & industry
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Atromentin is a member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxycyclohexa-2,5-diene-1,4-dione which is substituted by a 4-hydroxyphenyl group at positions 3 and 6. It is a mushroom pigment isolated from several fungi species and acts as a smooth muscle stimulant, and exhibits anticoagulant, antibacterial and antineoplastic properties. It has a role as a fungal metabolite, an EC 1.3.1.9 [enoyl-[acyl-carrier-protein] reductase (NADH)] inhibitor, a biological pigment, an anticoagulant, an apoptosis inducer, an antineoplastic agent and an antibacterial agent. It is a member of dihydroxy-1,4-benzoquinones and a polyphenol. It is a conjugate acid of an atromentin(1-).
Related reactions
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Compound notes
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