ContaminantDB: Noscapine

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

Record Information

Version

1.0

Creation Date

2016-05-22 03:44:26 UTC

Update Date

2016-11-09 01:15:28 UTC

Accession Number

CHEM016814

Identification

Common Name

Noscapine

Class

Small Molecule

Description

A benzylisoquinoline alkaloid that is 1,2,3,4-tetrahydroisoquinoline which is substituted by a 4,5-dimethoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl group at position 1, a methylenedioxy group at positions 6-7 and a methoxy group at position 8. Obtained from plants of the Papaveraceae family, it lacks significant painkilling properties and is primarily used for its antitussive (cough-suppressing) effects.

Contaminant Sources

FooDB Chemicals
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

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

Synonyms

Value	Source
(-)-Narcotine	ChEBI
alpha-Narcotine	ChEBI
Noscapina	ChEBI
Noscapine	ChEBI
Noscapinum	ChEBI
a-Narcotine	Generator
Α-narcotine	Generator
(-)-a-Narcotine	Generator
(-)-Α-narcotine	Generator
Capval	MeSH
Capval tropfen	MeSH
Embonate, noscapine hydrogen	MeSH
Hydrochloride, noscapine	MeSH
Hydrogen embonate, noscapine	MeSH
Librochin prikkelhoest	MeSH
Narcotine	MeSH
Noscapect	MeSH
Noscapine hydrochloride	MeSH
Noscapine hydrogen embonate	MeSH
Tropfen, capval	MeSH
Tuscalman	MeSH
Prikkelhoest, librochin	MeSH
(-)-alpha-Narcotine	ChEBI
Coscopin	HMDB
L-alpha-Narcotine	HMDB
Longatin	HMDB
Lyobex	HMDB
Methoxyhydrastine	HMDB
Narcompren	HMDB
Narcosine	HMDB
Narcotin	HMDB
Narcotussin	HMDB
Narkotin	HMDB
Nectadon	HMDB
Nicolane	HMDB
Nipaxon	HMDB
Noscapal	HMDB
Noscapalin	HMDB
Noscapin	HMDB
Noscapine (JP15/usp/inn)	HMDB
Noscopine	HMDB
O-Methylnarcotoline	HMDB
Opian	HMDB
Opianin	HMDB
Opianine	HMDB
Terbenol	HMDB
Tusscapine	HMDB
Vadebex	HMDB

Chemical Formula

C₂₂H₂₃NO₇

Average Molecular Mass

413.421 g/mol

Monoisotopic Mass

413.147 g/mol

CAS Registry Number

128-62-1

IUPAC Name

(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-one

Traditional Name

noscapine

SMILES

[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]1([H])N(C)CCC2=CC3=C(OCO3)C(OC)=C12

InChI Identifier

InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1

InChI Key

AKNNEGZIBPJZJG-MSOLQXFVSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Phthalide isoquinolines

Sub Class

Not Available

Direct Parent

Phthalide isoquinolines

Alternative Parents

Substituents

Phthalide isoquinoline
Isobenzofuranone
Benzofuranone
Tetrahydroisoquinoline
Phthalide
Benzodioxole
Isocoumaran
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary aliphatic amine
Tertiary amine
Acetal
Carboxylic acid derivative
Oxacycle
Ether
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:73237 )
benzylisoquinoline alkaloid (CHEBI:73237 )
cyclic acetal (CHEBI:73237 )
isobenzofuranone (CHEBI:73237 )
Isoquinoline alkaloids (C09592 )

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	0.18 g/L	ALOGPS
logP	2	ALOGPS
logP	2.58	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.59	ChemAxon
pKa (Strongest Basic)	6.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	75.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.08 m³·mol⁻¹	ChemAxon
Polarizability	42.19 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 GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0090000000-32e92f98445c85eff993	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-00di-0090000000-d382091e1ec4d8b38b31	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00di-0092000000-b90243e40af9870ee7a7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00di-0091000000-a54e072ef1d92f81334d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00di-0091000000-fce496b34ef93b8f503f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0ab9-0040900000-47e532749f5b8ffb3ccc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00di-0002900000-254fac469b3a08249319	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-0494000000-cb9d8aed31ebc22f9c22	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-03k9-0062900000-bf0cf5fac123965ac7b1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-0089300000-86a4acdf0e1666ee2f5d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-0097000000-3dc8b045aeb87b81f488	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0096200000-0e46351b9e099dd035ff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-0097000000-2c38fbf5a5a8273cb562	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-03k9-0062900000-d48438307b64d04a2721	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0010900000-a69d344c6c2917e1894f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0013900000-5b826e3916f6a190b5d4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03k9-0349500000-0a1171b8ad158af511de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f96-1938000000-0226d383a4c62f6dd51a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0002900000-3e5155cb1df43a1ee339	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03yj-0009300000-554dd8c085d71b8e8c59	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0i6u-1109000000-3b5e0f2ae056ecae25b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-3a2b668bf2dbd5c6416c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0007900000-6699c8e8d0e97bb3ffff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ot-0549100000-6e0506ecee44b088751b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0010900000-def7e1eece373bfc3cb7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0031900000-3d606db82b215faa9e7e	Spectrum