caldariellaquinone (PAMDB120026)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120026
Identification
Name: caldariellaquinone
Description:A 1-benzothiophene that is 1-benzothiophene-4,7-dione bearing additional methylthio and 3,7,11,15,19,23-hexamethyltetracosyl substituents at positions 5 and 6 respectively. Isolated from Caldariella acidophila.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 6-(3,7,11,15,19,23-hexamethyltetracosyl)-5-methylthiobenzo[b]thiophen-4,7-quinone
  • caldariellaquinone
Chemical Formula: C39H66O2S2
Average Molecular Weight: 631.069
Monoisotopic Molecular Weight: 630.45044
InChI Key: GHRWXPXOBGRSHG-UHFFFAOYSA-N
InChI:InChI=1S/C39H66O2S2/c1-28(2)14-9-15-29(3)16-10-17-30(4)18-11-19-31(5)20-12-21-32(6)22-13-23-33(7)24-25-34-37(41)39-35(26-27-43-39)36(40)38(34)42-8/h26-33H,9-25H2,1-8H3
CAS number: Not Available
IUPAC Name:6-(3,7,11,15,19,23-hexamethyltetracosyl)-5-(methylsulfanyl)-1-benzothiophene-4,7-dione
Traditional IUPAC Name: Not Available
SMILES:CC(C)CCCC(C)CCCC(C)CCCC(C)CCCC(C)CCCC(C)CCC2(=C(SC)C(=O)C1(=C(SC=C1)C(=O)2))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Prenol lipids
Sub ClassSesterterpenoids
Direct Parent Sesterterpenoids
Alternative Parents
Substituents
  • Sesterterpenoid
  • Aryl ketone
  • Vinylogous thioester
  • Heteroaromatic compound
  • Thiophene
  • Thioenolether
  • Ketone
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
  • 1-benzothiophenes, quinone, organic sulfide (CHEBI:73387)
  • a quinone (CPD-9612)
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Molecular Weight631.075 g/molPubChem
XLogP3-AA16.4 PubChem
Hydrogen Bond Donor Count0 PubChem
Hydrogen Bond Acceptor Count4 PubChem
Rotatable Bond Count24 PubChem
Exact Mass630.45 g/molPubChem
Monoisotopic Mass630.45 g/molPubChem
Topological Polar Surface Area87.7 A^2PubChem
Heavy Atom Count43 PubChem
Formal Charge0 PubChem
Complexity833 PubChem
Isotope Atom Count0 PubChem
Defined Atom Stereocenter Count0 PubChem
Undefined Atom Stereocenter Count5 PubChem
Defined Bond Stereocenter Count0 PubChem
Undefined Bond Stereocenter Count0 PubChem
Covalently-Bonded Unit Count1 PubChem
Biological Properties
Cellular Locations: Not Available
Reactions:
caldariellaquinone + Hydrogen ion → caldariellaquinol
caldariellaquinone + succinate → caldariellaquinol + fumarate
Pathways:
    Spectra
    Spectra: Not Available
    References
    References:
    • Zhou D, White RH (1989)Biosynthesis of caldariellaquinone in Sulfolobus spp. Journal of bacteriology 171, Pubmed: 2512282
    • Collins MD, Langworthy TA (1983)Respiratory quinone composition of some acidophilic bacteria. Systematic and applied microbiology 4, Pubmed: 23194730
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    METABOLIGHTSMTBLC73387
    CHEBI73387
    CHEMSPIDER168476
    PUBCHEM194166