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Showing Compound Retrocalamin (FDB017389)

Record Information
Version1.0
Creation date2010-04-08 22:13:04 UTC
Update date2019-11-26 03:14:46 UTC
Primary IDFDB017389
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRetrocalamin
DescriptionRetrocalamin 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. Retrocalamin has been detected, but not quantified in, citrus and mandarin orange (clementine, tangerine). This could make retrocalamin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Retrocalamin.
CAS Number74729-98-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC24H30O9
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
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
Isomeric 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
Average Molecular Weight462.4896
Monoisotopic Molecular Weight462.188982558
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSRetrocalamin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000l-8094700000-e84539d1a96b2eaacabcSpectrum
Predicted GC-MSRetrocalamin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-5113390000-b745844ba820a3979fbdSpectrum
Predicted GC-MSRetrocalamin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ea-0002900000-f1e23378f7df0013eba92016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pk-0025900000-08c8e7b2ad7562b5735c2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-9445100000-566a6c53026cd23c39e52016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02t9-1002900000-0ac5571702404b7a3a9b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-046u-3003900000-4f227bb53fe349a4a1d82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00rb-9007200000-3d5b1406c177f3410edc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0007900000-865f5de2769a0391138f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-1009100000-3340b864685e66abec2b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2009000000-abe26dfb1843e1cdafb02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1006900000-64b5150fba9dbb285ebc2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-1009800000-2ec2e9e82b9dacc36b2a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-3029100000-c02424b4afd941bfde942021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38159
CRC / DFC (Dictionary of Food Compounds) IDKXM09-Z:KXM09-Z
EAFUS IDNot Available
Dr. Duke IDRETROCALAMIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).