Record Information
Version1.0
Creation date2010-04-08 22:11:12 UTC
Update date2019-11-26 03:09:49 UTC
Primary IDFDB014309
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMonotropein
DescriptionMonotropein belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. Based on a literature review a small amount of articles have been published on Monotropein.
CAS Number5945-50-6
Structure
Thumb
Synonyms
SynonymSource
Monotropein (8ci)HMDB
MonotropeineHMDB
7-Hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,7H,7ah-cyclopenta[c]pyran-4-carboxylateGenerator
Monotropein (8CI)biospider
Predicted Properties
PropertyValueSource
Water Solubility50.2 g/LALOGPS
logP-1.9ALOGPS
logP-3.3ChemAxon
logS-0.89ALOGPS
pKa (Strongest Acidic)4.14ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity85.02 m³·mol⁻¹ChemAxon
Polarizability36.41 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H22O11
IUPAC name7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid
InChI IdentifierInChI=1S/C16H22O11/c17-3-8-10(19)11(20)12(21)15(26-8)27-14-9-6(1-2-16(9,24)5-18)7(4-25-14)13(22)23/h1-2,4,6,8-12,14-15,17-21,24H,3,5H2,(H,22,23)
InChI KeyHPWWQPXTUDMRBI-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2OC=C(C3C=CC(O)(CO)C23)C(O)=O)C(O)C(O)C1O
Average Molecular Weight390.3393
Monoisotopic Molecular Weight390.116211546
Classification
Description Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentIridoid O-glycosides
Alternative Parents
Substituents
  • Iridoid o-glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • Iridoid-skeleton
  • O-glycosyl compound
  • Bicyclic monoterpenoid
  • Monoterpenoid
  • Monosaccharide
  • Oxane
  • Vinylogous ester
  • Tertiary alcohol
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Primary alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 49.23%; H 5.68%; O 45.09%DFC
Melting PointMp 175° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]18D -127.7 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMonotropein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00e9-7319000000-8b5ce8f8a4abf23af66eSpectrum
Predicted GC-MSMonotropein, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ik9-2612029000-2549ee86ef1c0583201bSpectrum
Predicted GC-MSMonotropein, TBDMS_4_26, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMonotropein, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMonotropein, "Monotropein,4TBDMS,#26" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03mi-0697000000-9c87dfb93fc61a7ba3792015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0983000000-d4d4b3be75fda92d8cd12015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-2940000000-223b8ce1cff9a72b632c2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03mi-0697000000-9c87dfb93fc61a7ba3792015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0983000000-d4d4b3be75fda92d8cd12015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-2940000000-223b8ce1cff9a72b632c2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0550-1469000000-dae4b0e9dd8ab7d5b0e52015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0730-2945000000-2c7a4b8e85c8cb6abf692015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-4920000000-dab947e989b907e721662015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0550-1469000000-dae4b0e9dd8ab7d5b0e52015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0730-2945000000-2c7a4b8e85c8cb6abf692015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-4920000000-dab947e989b907e721662015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0119000000-115f4c59160bfd59b02c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0975000000-fec3a124d98481fd7e092021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0arr-9842000000-0997e827175905c51ce72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0119000000-9d6848b034f0fef379552021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0570-8898000000-26926c245d193482b5072021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7l-9751000000-8168fbd0c87860fa8f5e2021-09-23View Spectrum
NMRNot Available
ChemSpider ID2729121
ChEMBL IDNot Available
KEGG Compound IDC09788
Pubchem Compound ID3488508
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35608
CRC / DFC (Dictionary of Food Compounds) IDJPM12-G:JPM12-G
EAFUS IDNot Available
Dr. Duke IDMONOTROPEIN
BIGG IDNot Available
KNApSAcK IDC00003089
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
cathartic75325 Any substance that accelerates defecation. Compare with laxatives, which are substances that ease defecation (usually by softening faeces). A substance can be both a laxative and a cathartic.DUKE
laxative50503 An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.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).