Secalonic Acid D (CHEM002738)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2010-05-26 16:48:09 UTC
Update Date2026-04-06 12:47:13 UTC
Accession NumberCHEM002738
Identification
Common NameSecalonic Acid D
ClassSmall Molecule
DescriptionSecalonic acid D (SAD) is a mycotoxin produced by the fungus Pencillium oxalicum, which is a common contaminant in corn and other grains. Secalonic acid D is a human teratogen that induces cleft palate. (1)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Ester
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Secalonate DGenerator
Secalonic acidMeSH
Secalonic acid aMeSH
Chemical FormulaC32H30O14
Average Molecular Mass638.572 g/mol
Monoisotopic Mass638.164 g/mol
CAS Registry Number35287-69-5
IUPAC Namemethyl 4,8,9-trihydroxy-3-methyl-1-oxo-7-[4,8,9-trihydroxy-4a-(methoxycarbonyl)-3-methyl-1-oxo-2,3,4,4a-tetrahydro-1H-xanthen-7-yl]-2,3,4,4a-tetrahydro-1H-xanthene-4a-carboxylate
Traditional Namesecalonic acid D
SMILESCOC(=O)C12OC3=C(C(O)=C(C=C3)C3=C(O)C4=C(OC5(C(O)C(C)CC(=O)C5=C4O)C(=O)OC)C=C3)C(O)=C1C(=O)CC(C)C2O
InChI IdentifierInChI=1S/C32H30O14/c1-11-9-15(33)21-25(37)19-17(45-31(21,27(11)39)29(41)43-3)7-5-13(23(19)35)14-6-8-18-20(24(14)36)26(38)22-16(34)10-12(2)28(40)32(22,46-18)30(42)44-4/h5-8,11-12,27-28,35-40H,9-10H2,1-4H3
InChI KeyNFZJAYYORNVZNI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentXanthenes
Alternative Parents
Substituents
  • Xanthene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Hydroxy acid
  • Cyclic alcohol
  • Vinylogous acid
  • Methyl ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Ketone
  • Ether
  • Enol
  • Oxacycle
  • Carboxylic acid derivative
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP1.62ALOGPS
logP1.19ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)5.57ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area226.58 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity156.5 m³·mol⁻¹ChemAxon
Polarizability63.29 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000209000-fbd21faaff04fd0994e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-009i-1341429000-8e5a7a842c2b59ca5334Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-1090000000-db059c3481746c5817f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000119000-2f2c44ebedcf7b00751cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00p0-0254419000-2a03bc319b29191e5c61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1559250000-6cfd148c809a2998b5ddSpectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (4)
Mechanism of ToxicitySecalonic acid D (SAD) is though to induce cleft palate by causing the formation of smaller palatal shelves that fail to elevate and fuse. This inhibited palatal shelf growth is a result of the of SAD causing reduced proliferation of embryonic palatal mesenchymal (HEPM) cells. SAD binds to and phosphorylates cAMP response element binding protein (CREB), an important transcription factor required for the expression of numerous genes including proliferating cell nuclear antigen (PCNA) gene. The phosphorylation of CREB by SAD prevents it from forming the necessary transcription factor-cAMP response element complex at transcription start sites, so these genes are not expressed. This leads to reduced palatal mesenchymal cell number causing reduced palatal shelf growth and thus cleft palate. (1, 2, 3)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesSecalonic acid D (SAD) is a mycotoxin produced by the fungus Pencillium oxalicum, which is a common contaminant in corn and other grains. (1)
Minimum Risk LevelNot Available
Health EffectsSecalonic acid D is a human teratogen that induces cleft palate. (1)
SymptomsCleft palate is a congenital deformity characterized by a gap on the roof of the mouth that is present at birth. (3)
TreatmentCleft palate can be treated with corrective surgery. (3)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0258201
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00048115
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID375257
ChEBI IDNot Available
PubChem Compound ID423972
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available