ContaminantDB: Simmondsin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 21:41:17 UTC

Update Date

2016-11-09 01:17:53 UTC

Accession Number

CHEM024419

Identification

Common Name

Simmondsin

Class

Small Molecule

Description

Simmondsin is found in coffee and coffee products. Simmondsin is a constituent of Simmondsia chinensis (jojoba) Simmondsin is an extract of jojoba seeds (pronounced "ho-HO-bah") (Simmondsia chinensis), it was traditionally thought to be a toxic substance due to jojoba seed meal causing weight loss in animals, but recently it has been researched as a potential treatment for reducing appetite of obese individuals by helping to reduce craving for food. Several mechanisms of action are thought to be involved in the appetite suppressant effect

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Cyanomethylene-1-glucosyloxy-3-hydroxy-4,5-dimethoxycyclohexane	HMDB
[6-(b-D-Glucopyranosyloxy)-2-hydroxy-3,4-dimethoxycyclohexylidene]acetonitrile, 9ci	HMDB
2-(Cyanomethylene)-3-hydroxy-4,5-dimethoxycyclohexyl-beta-glucoside	HMDB
Simmondsin	MeSH

Chemical Formula

C₁₆H₂₅NO₉

Average Molecular Mass

375.371 g/mol

Monoisotopic Mass

375.153 g/mol

CAS Registry Number

51771-52-9

IUPAC Name

2-[(1E)-2-hydroxy-3,4-dimethoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile

Traditional Name

2-[(1E)-2-hydroxy-3,4-dimethoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile

SMILES

COC1CC(OC2OC(CO)C(O)C(O)C2O)\C(=C\C#N)C(O)C1OC

InChI Identifier

InChI=1S/C16H25NO9/c1-23-9-5-8(7(3-4-17)11(19)15(9)24-2)25-16-14(22)13(21)12(20)10(6-18)26-16/h3,8-16,18-22H,5-6H2,1-2H3/b7-3-

InChI Key

KURSRHBVYUACKS-CLTKARDFSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
Cyclitol or derivatives
Monosaccharide
Oxane
Cyclic alcohol
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Nitrile
Carbonitrile
Oxacycle
Ether
Dialkyl ether
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Alcohol
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	50.6 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-2.9	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.86 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.85 m³·mol⁻¹	ChemAxon
Polarizability	36.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pbc-6709000000-6998950778cd28d8115f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0002-5700029000-7d5f45c590134067edbc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-08i1-0859000000-75c9aa237be28bb87161	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0931000000-334b1b9ad66bce406d80	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6t-9810000000-7e46d7dfb818bceb9ef2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0229-1549000000-f17a64c9d81a11e6b273	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dj-2942000000-754398f69da1c15e0816	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0295-5930000000-dc664cfc0e9ff444576b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0119000000-d8c528e451fd3e295a78	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-0933000000-3b292e8d59637d682a1d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08fr-7690000000-c0bd49d4c6ff3a7fbb04	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0019000000-a564b8e7ffa695a32dd3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0c00-3879000000-f826e8fc4fa488e85bb0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052b-8941000000-de6b200cc3b38374a3e6	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0030394

FooDB ID

FDB002248

Phenol Explorer ID

Not Available

KNApSAcK ID

C00054414

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Simmondsin

Chemspider ID

4733931

ChEBI ID

Not Available

PubChem Compound ID

5884740

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Simmondsin (CHEM024419)

Structure for CHEM024419: Simmondsin