Showing Compound Monotropein (FDB014309)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:12 UTC

Update date

2019-11-26 03:09:49 UTC

Primary ID

FDB014309

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Monotropein

Description

Monotropein 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 Number

5945-50-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Monotropein (8ci)	HMDB
Monotropeine	HMDB
7-Hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,7H,7ah-cyclopenta[c]pyran-4-carboxylate	Generator
Monotropein (8CI)	biospider

Predicted Properties

Property	Value	Source
Water Solubility	50.2 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-3.3	ChemAxon
logS	-0.89	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.02 m³·mol⁻¹	ChemAxon
Polarizability	36.41 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C16H22O11

IUPAC name

7-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 Identifier

InChI=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 Key

HPWWQPXTUDMRBI-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(OC2OC=C(C3C=CC(O)(CO)C23)C(O)=O)C(O)C(O)C1O

Average Molecular Weight

390.3393

Monoisotopic Molecular Weight

390.116211546

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid 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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Flavoring agent

Pharmaceutical industry:

Anti-inflammatory

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 49.23%; H 5.68%; O 45.09%	DFC
Melting Point	Mp 175° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]18D -127.7 (H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Monotropein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00e9-7319000000-8b5ce8f8a4abf23af66e	Spectrum
Predicted GC-MS	Monotropein, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ik9-2612029000-2549ee86ef1c0583201b	Spectrum
Predicted GC-MS	Monotropein, TBDMS_4_26, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Monotropein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Monotropein, "Monotropein,4TBDMS,#26" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03mi-0697000000-9c87dfb93fc61a7ba379	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0983000000-d4d4b3be75fda92d8cd1	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-2940000000-223b8ce1cff9a72b632c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03mi-0697000000-9c87dfb93fc61a7ba379	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0983000000-d4d4b3be75fda92d8cd1	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-2940000000-223b8ce1cff9a72b632c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0550-1469000000-dae4b0e9dd8ab7d5b0e5	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0730-2945000000-2c7a4b8e85c8cb6abf69	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06tf-4920000000-dab947e989b907e72166	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0550-1469000000-dae4b0e9dd8ab7d5b0e5	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0730-2945000000-2c7a4b8e85c8cb6abf69	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06tf-4920000000-dab947e989b907e72166	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0119000000-115f4c59160bfd59b02c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-0975000000-fec3a124d98481fd7e09	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0arr-9842000000-0997e827175905c51ce7	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0119000000-9d6848b034f0fef37955	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0570-8898000000-26926c245d193482b507	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a7l-9751000000-8168fbd0c87860fa8f5e	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

2729121

ChEMBL ID

Not Available

KEGG Compound ID

C09788

Pubchem Compound ID

3488508

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB35608

CRC / DFC (Dictionary of Food Compounds) ID

JPM12-G:JPM12-G

EAFUS ID

Not Available

Dr. Duke ID

MONOTROPEIN

BIGG ID

Not Available

KNApSAcK ID

C00003089

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
cathartic	75325	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
laxative	50503	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