Retrocalamin (CHEM031545)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:43:58 UTC
Update Date2016-11-09 01:19:17 UTC
Accession NumberCHEM031545
Identification
Common NameRetrocalamin
ClassSmall Molecule
DescriptionConstituent of calamondin seeds (Citrus reticulata). Retrocalamin is found in citrus.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Methyl (3S)-3-[(1R,2S,6S,10S,11R,14S)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]-3-hydroxypropanoic acidGenerator
Chemical FormulaC24H30O9
Average Molecular Mass462.490 g/mol
Monoisotopic Mass462.189 g/mol
CAS Registry Number74729-98-9
IUPAC Namemethyl (3S)-3-[(1R,2S,6S,10S,11R,14S)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]-3-hydroxypropanoate
Traditional Namemethyl (3S)-3-[(1R,2S,6S,10S,11R,14S)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]-3-hydroxypropanoate
SMILESCOC(=O)C[C@H](O)[C@@]1(C)CC(=O)C(O)[C@]2(C)C1CC[C@@]1(C)[C@@H](OC(=O)[C@H]3O[C@@]213)C1=COC=C1
InChI IdentifierInChI=1S/C24H30O9/c1-21(15(26)9-16(27)30-4)10-13(25)17(28)23(3)14(21)5-7-22(2)18(12-6-8-31-11-12)32-20(29)19-24(22,23)33-19/h6,8,11,14-15,17-19,26,28H,5,7,9-10H2,1-4H3/t14?,15-,17?,18-,19+,21-,22-,23-,24+/m0/s1
InChI KeyHMNKPIJMXBZMJF-IHGWNHGOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNot Available
Direct ParentNaphthopyrans
Alternative Parents
Substituents
  • Naphthopyran
  • Naphthalene
  • Delta_valerolactone
  • 1,4-dioxepane
  • Beta-hydroxy acid
  • Fatty acid ester
  • Dioxepane
  • Delta valerolactone
  • Pyran
  • Oxane
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Hydroxy acid
  • Furan
  • Methyl ester
  • Heteroaromatic compound
  • Cyclic alcohol
  • Carboxylic acid ester
  • Cyclic ketone
  • Secondary alcohol
  • Lactone
  • Ketone
  • Dialkyl ether
  • Oxacycle
  • Carboxylic acid derivative
  • Oxirane
  • Ether
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Aromatic heteropolycyclic compound
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 Solubility0.2 g/LALOGPS
logP1.51ALOGPS
logP1.21ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.86ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area135.8 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity110.54 m³·mol⁻¹ChemAxon
Polarizability46.51 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-8094700000-e84539d1a96b2eaacabcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0006-5113390000-b745844ba820a3979fbdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ea-0002900000-f1e23378f7df0013eba9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pk-0025900000-08c8e7b2ad7562b5735cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-9445100000-566a6c53026cd23c39e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02t9-1002900000-0ac5571702404b7a3a9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-046u-3003900000-4f227bb53fe349a4a1d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00rb-9007200000-3d5b1406c177f3410edcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0007900000-865f5de2769a0391138fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-1009100000-3340b864685e66abec2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2009000000-abe26dfb1843e1cdafb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1006900000-64b5150fba9dbb285ebcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-1009800000-2ec2e9e82b9dacc36b2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-3029100000-c02424b4afd941bfde94Spectrum
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 IDHMDB0038159
FooDB IDFDB017389
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID131752313
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.