Record Information
Version1.0
Creation date2010-04-08 22:06:10 UTC
Update date2019-11-26 02:59:55 UTC
Primary IDFDB004288
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIntermedine
DescriptionIntermedine, also known as 9-(+)-trachelanthylretronecine or beta-msh, belongs to alkaloids and derivatives class of compounds. Those are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic propertiesand is 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. Intermedine is soluble (in water) and a very weakly acidic compound (based on its pKa). Intermedine can be found in borage, which makes intermedine a potential biomarker for the consumption of this food product.
CAS Number10285-06-0
Structure
Thumb
Synonyms
SynonymSource
9-(+)-TrachelanthylretronecineChEBI
beta-MSHChEBI
IntermedinaChEBI
IntermedinumChEBI
b-MSHGenerator
Β-MSHGenerator
Beta-melanocyte-stimulating hormonebiospider
Beta-melanotropinbiospider
Beta-MSHbiospider
Intermedinbiospider
Intermedinebiospider
Mel-stimulating hormonebiospider
Melanocyte stimulating hormonesbiospider
Melanocyte-stimulating hormonesbiospider
Melanophore hormonebiospider
Melanophore stimulating hormonebiospider
Melanophore-expanding hormonebiospider
Melanophore-stimulating hormonebiospider
Melanotropinbiospider
MSHbiospider
MSH (melanocyte-stimulating hormones)biospider
Pigment hormonebiospider
Predicted Properties
PropertyValueSource
Water Solubility50.8 g/LALOGPS
logP0.41ALOGPS
logP-0.29ChemAxon
logS-0.77ALOGPS
pKa (Strongest Acidic)11.34ChemAxon
pKa (Strongest Basic)8.82ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.23 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity77.94 m³·mol⁻¹ChemAxon
Polarizability31.65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H25NO5
IUPAC name[(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-hydroxyethyl]-3-methylbutanoate
InChI IdentifierInChI=1S/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,12-,13-,15+/m1/s1
InChI KeySFVVQRJOGUKCEG-OPQSFPLASA-N
Isomeric SMILES[H][C@@]12[C@H](O)CCN1CC=C2COC(=O)[C@](O)(C(C)C)[C@@H](C)O
Average Molecular Weight299.3627
Monoisotopic Molecular Weight299.173272915
Classification
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
  • Alkaloid or derivatives
  • Pyrrolizine
  • Beta-hydroxy acid
  • Fatty acid ester
  • Hydroxy acid
  • N-alkylpyrrolidine
  • Fatty acyl
  • Tertiary alcohol
  • Pyrroline
  • Pyrrolidine
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0894000000-0ca28f402d6c3271b3a2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dv-5930000000-4468609a3d1860632eefSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007a-7900000000-5a507c75289e1cb511d8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-1690000000-463ea0b40b7c8f9f7914Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02aa-1960000000-f1389da2df24657ebf1eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xs-9500000000-374e4d150e4fd3eaa16fSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC10330
Pubchem Compound ID114843
Pubchem Substance IDNot Available
ChEBI ID5941
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDINTERMEDINE
BIGG IDNot Available
KNApSAcK IDC00002093
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
hepatotoxic50908 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.DUKE
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).