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(+)-Erythraline (CHEM024280)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:36:25 UTC
Update Date2016-11-09 01:17:51 UTC
Accession NumberCHEM024280
Identification
Common Name(+)-Erythraline
ClassSmall Molecule
DescriptionAlkaloid from Erythrina glauca (gallito) Alitretinoin (9-cis-retinoic acid) is a naturally-occurring endogenous retinoid indicated for topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma. Alitretinoin inhibits the growth of Kaposi's sarcoma (KS) cells in vitro.; Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately control anterior/posterior patterning in early developmental stages. Retinoic acid acts by binding to heterodimers of the retinoic acid receptor (RAR) and the retinoid X receptor (RXR), which then bind to retinoic acid response elements (RAREs) in the regulatory regions of direct targets (including Hox genes), thereby activating gene transcription. Retinoic acid receptors mediate transcription of different sets of genes of cell differentiation, thus it also depends on the target cells. One of the target genes is the gene of the retinoic acid receptor itself which occurs during positive regulation. Control of retinoic acid levels is maintained by a suite of proteins.; Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID: 17495912). It is an important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth and embryonic development. An excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute). (+)-Erythraline is found in green vegetables.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
ErythralineHMDB
Chemical FormulaC18H19NO3
Average Molecular Mass297.348 g/mol
Monoisotopic Mass297.136 g/mol
CAS Registry Number466-77-3
IUPAC Name19-methoxy-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2(10),3,8,15,17-pentaene
Traditional Name19-methoxy-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2(10),3,8,15,17-pentaene
SMILESCOC1CC23N(CC=C2C=C1)CCC1=C3C=C2OCOC2=C1
InChI IdentifierInChI=1S/C18H19NO3/c1-20-14-3-2-13-5-7-19-6-4-12-8-16-17(22-11-21-16)9-15(12)18(13,19)10-14/h2-3,5,8-9,14H,4,6-7,10-11H2,1H3
InChI KeyTVOFUERNMZTYRM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as erythrinanes. These are erythrina alkaloids possessing either a 6-5-6-6-membered indoloisoquinoline core or a derivative thereof.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassErythrina alkaloids
Sub ClassErythrinanes
Direct ParentErythrinanes
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.05 g/LALOGPS
logP2.01ALOGPS
logP2ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)9.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.93 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity85.28 m³·mol⁻¹ChemAxon
Polarizability32.08 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-015i-0190000000-31a215c71d077d41cd3cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-4ed4932343e54c47b889Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0090000000-3f45afeb82d24f91e26fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-1690000000-ea46bd1a5bb5184fcba8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-e65fe867119975c81d74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-118fb68f55dae0d84902Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f89-1190000000-17347a064f6a1d40eb77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-620f87966eb750d6f48dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0090000000-e0c9e93842a5dcbc6fafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-0290000000-50da91a2cb3d44278298Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-f0a7b42101b1968126a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-6e7152719730c22b3e4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001v-0190000000-8022183ddbfa6a633fa5Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030258
FooDB IDFDB002082
Phenol Explorer IDNot Available
KNApSAcK IDC00027355
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID26504826
ChEBI IDNot Available
PubChem Compound ID12308897
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Holland LZ: Developmental biology: a chordate with a difference. Nature. 2007 May 10;447(7141):153-5.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.