ContaminantDB: Rauwolscine

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

Record Information

Version

1.0

Creation Date

2016-05-22 05:15:18 UTC

Update Date

2016-11-09 01:15:48 UTC

Accession Number

CHEM018436

Identification

Common Name

Rauwolscine

Class

Small Molecule

Description

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
17alpha-Hydroxy-20alpha-yohimban-16beta-carboxylic acid methyl ester	ChEBI
alpha-Yohimbine	ChEBI
Corynanthidine	ChEBI
Isoyohimbine	ChEBI
Mesoyohimbine	ChEBI
Methyl (16beta,17alpha,20alpha)-17-hydroxyyohimban-16-carboxylate	ChEBI
17a-Hydroxy-20a-yohimban-16b-carboxylate methyl ester	Generator
17a-Hydroxy-20a-yohimban-16b-carboxylic acid methyl ester	Generator
17alpha-Hydroxy-20alpha-yohimban-16beta-carboxylate methyl ester	Generator
17Α-hydroxy-20α-yohimban-16β-carboxylate methyl ester	Generator
17Α-hydroxy-20α-yohimban-16β-carboxylic acid methyl ester	Generator
a-Yohimbine	Generator
Α-yohimbine	Generator
Methyl (16b,17a,20a)-17-hydroxyyohimban-16-carboxylate	Generator
Methyl (16b,17a,20a)-17-hydroxyyohimban-16-carboxylic acid	Generator
Methyl (16beta,17alpha,20alpha)-17-hydroxyyohimban-16-carboxylic acid	Generator
Methyl (16β,17α,20α)-17-hydroxyyohimban-16-carboxylate	Generator
Methyl (16β,17α,20α)-17-hydroxyyohimban-16-carboxylic acid	Generator
Methyl (1S,15S,18S,19S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid	Generator
Aphrodyne	MeSH
Hydrochloride, aphrodine	MeSH
Solvay brand OF yohimbine hydrochloride	MeSH
Yocon	MeSH
Yohimbine	MeSH
Aphrodine hydrochloride	MeSH
Palisades brand OF yohimbine hydrochloride	MeSH
Pluriviron	MeSH
Rauwolscine	MeSH
Corynanthine	MeSH
Kramer brand OF yohimbine hydrochloride	MeSH
Rauhimbine	MeSH
Yohimbine houdé	MeSH
Yohimex	MeSH
Hydrochloride, yohimbine	MeSH
Yohimbin spiegel	MeSH
Corynanthine tartrate	MeSH
Glenwood brand OF yohimbine hydrochloride	MeSH
Star brand OF yohimbine hydrochloride	MeSH
Tartrate, corynanthine	MeSH
StegroPharm brand OF yohimbine hydrochloride	MeSH
Aventis brand OF yohimbine hydrochloride	MeSH
Yohimbine hydrochloride	MeSH

Chemical Formula

C₂₁H₂₆N₂O₃

Average Molecular Mass

354.450 g/mol

Monoisotopic Mass

354.194 g/mol

CAS Registry Number

131-03-3

IUPAC Name

methyl (1S,15S,18S,19S,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

Traditional Name

rauwolscine

SMILES

[H][C@]1(O)CC[C@]2([H])CN3CCC4=C(NC5=CC=CC=C45)[C@]3([H])C[C@]2([H])[C@]1([H])C(=O)OC

InChI Identifier

InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15+,17+,18+,19+/m1/s1

InChI Key

BLGXFZZNTVWLAY-DIRVCLHFSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as chlorins. These are large heterocyclic aromatic ring systems consisting, at the core, of three pyrroles and one pyrroline coupled through four methine linkages.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Chlorins

Direct Parent

Chlorins

Alternative Parents

Substituents

Chlorin
Tetracarboxylic acid or derivatives
Isoindole or derivatives
Fatty acid ester
Substituted pyrrole
Fatty acyl
Pyrrole
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methyl ester (CHEBI:60778 )
carboxylic acid (CHEBI:60778 )
beta-substituted porphyrin (CHEBI:60778 )

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	0.35 g/L	ALOGPS
logP	2.36	ALOGPS
logP	2.1	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	14.68	ChemAxon
pKa (Strongest Basic)	7.48	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.63 m³·mol⁻¹	ChemAxon
Polarizability	39.87 Å³	ChemAxon
Number of Rings	5	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0019000000-98fd50566f845231fbed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-0129000000-49a3b77851cb2f327e51	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ffx-0891000000-1297a98bf2d980f32361	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-6448f2e7be3b7fa35128	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0009000000-a436855e9ddc5d8e061e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-07ef-3956000000-386e3fa9fb16f1a30cf6	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

Not Available

FooDB ID

Not Available

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

Rauwolscine

Chemspider ID

Not Available

ChEBI ID

48562

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Rauwolscine (CHEM018436)

Structure for CHEM018436: Rauwolscine