Riddelliine (CHEM016160)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:17:18 UTC
Update Date2016-11-09 01:15:20 UTC
Accession NumberCHEM016160
Identification
Common NameRiddelliine
ClassSmall Molecule
DescriptionA macrolide that is 13,19-didehydrosenecionan bearing two additional hydroxy substituents at positions 12 and 18 as well as two additional oxo groups at positions 11 and 16.
Contaminant Sources
  • IARC Carcinogens Group 2B
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
18-HydroxyseneciphyllineChEBI
RiddeliinChEBI
RiddeliineChEBI
RiddellineChEBI
Chemical FormulaC18H23NO6
Average Molecular Mass349.383 g/mol
Monoisotopic Mass349.153 g/mol
CAS Registry Number23246-96-0
IUPAC Name(1R,4Z,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
Traditional Nameriddelliine
SMILES[H]\C(C)=C1/CC(=C)[C@](O)(CO)C(=O)OCC2=CCN3CC[C@@]([H])(OC1=O)[C@@]23[H]
InChI IdentifierInChI=1S/C18H23NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,14-15,20,23H,2,5-10H2,1H3/b12-3-/t14-,15-,18-/m1/s1
InChI KeySVCNNZDUGWLODJ-RAYFHMIRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Senecionan-skeleton
  • Alkaloid or derivatives
  • Pyrrolizine
  • Dicarboxylic acid or derivatives
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Pyrroline
  • Tertiary alcohol
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Lactone
  • 1,2-diol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Organopnictogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
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 Solubility7.23 g/LALOGPS
logP0.6ALOGPS
logP0.33ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)11.11ChemAxon
pKa (Strongest Basic)7.14ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area96.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity90.65 m³·mol⁻¹ChemAxon
Polarizability34.89 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0609000000-a47389f915811bb84436Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0080-3915000000-38f16b43811244ab0b64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01c1-6900000000-996a8ead8cb6afd61903Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f7a-0829000000-c9fa7ef8f49463f9e5cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-4922000000-e7781acda390bf81ea98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9710000000-2bd2f4598c035542c4ffSpectrum
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 IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00002110
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRiddelliine
Chemspider IDNot Available
ChEBI ID63924
PubChem Compound ID5281744
Kegg Compound IDC10375
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11170513
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12140173
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14580895
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18842697
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19412857
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=1949039
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20078085
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=20737008
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=2083039
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21170807
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21822322
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21976715
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=3507253