ContaminantDB: (+)-Quebrachidine

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

Record Information

Version

1.0

Creation Date

2016-05-25 21:41:07 UTC

Update Date

2016-11-09 01:17:53 UTC

Accession Number

CHEM024415

Identification

Common Name

(+)-Quebrachidine

Class

Small Molecule

Description

(+)-Quebrachidine is an alkaloid from Aspidosperma quebracho-blanco (quebracho

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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
Methyl (10S,13E,16S,18S)-13-ethylidene-18-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylic acid	HMDB

Chemical Formula

C₂₁H₂₄N₂O₃

Average Molecular Mass

352.427 g/mol

Monoisotopic Mass

352.179 g/mol

CAS Registry Number

21641-60-1

IUPAC Name

methyl (10S,13E,16S,18S)-13-ethylidene-18-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate

Traditional Name

methyl (10S,13E,16S,18S)-13-ethylidene-18-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate

SMILES

COC(=O)C12[C@@H]3CC4(C(NC5=CC=CC=C45)[C@@H]4CC1\C(CN34)=C/C)[C@@H]2O

InChI Identifier

InChI=1S/C21H24N2O3/c1-3-11-10-23-15-8-13(11)21(19(25)26-2)16(23)9-20(18(21)24)12-6-4-5-7-14(12)22-17(15)20/h3-7,13,15-18,22,24H,8-10H2,1-2H3/b11-3-/t13?,15-,16-,17?,18-,20?,21?/m0/s1

InChI Key

RLUORQGMBKDXPO-CFAUMIGUSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Corynanthean-type alkaloids

Sub Class

Not Available

Direct Parent

Corynanthean-type alkaloids

Alternative Parents

Substituents

Corynanthean skeleton
Beta-carboline
Pyridoindole
Delta amino acid or derivatives
Quinolizidine
Indole or derivatives
Dihydroindole
Piperidinecarboxylic acid
Quinuclidine
Azepane
Beta-hydroxy acid
Aralkylamine
Secondary aliphatic/aromatic amine
Hydroxy acid
Benzenoid
Piperidine
Cyclic alcohol
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Secondary amine
Alcohol
Hydrocarbon derivative
Organic oxide
Amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	3.17 g/L	ALOGPS
logP	2.38	ALOGPS
logP	1.2	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	6.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.8 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.85 m³·mol⁻¹	ChemAxon
Polarizability	38.08 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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	splash10-0076-3049000000-1512485f53dac99bd342	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05g3-9004200000-c80d0efaafffc8a45e86	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	splash10-0udr-0009000000-861a7ed16f2918f700dc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ug0-0029000000-0985fd508474fa418573	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-2096000000-e2bc058d27a511d00e0f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-00bda9e8ec0b8b34a52a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0019000000-fb75b362b0dd374df4c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ko-0093000000-62d75063c7fd5ac92e6e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0019000000-40c487ceb6e346a1aed9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0029000000-db598bf64510018ca56e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udl-0069000000-8a9e1f50c6e35e081fcf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0049000000-63bd1a6a9039fd137926	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0090000000-a47e1d5b96b417632a5c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0090000000-4e71703a18aaccacc836	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

HMDB0030390

FooDB ID

FDB002243

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

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

6445097

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.

(+)-Quebrachidine (CHEM024415)

Structure for CHEM024415: (+)-Quebrachidine