Showing Compound (-)-alpha-Narcotine (FDB011477)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:40 UTC

Update date

2019-11-26 03:04:58 UTC

Primary ID

FDB011477

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(-)-alpha-Narcotine

Description

Alkaloid from Papaver somniferum (opium poppy) Noscapine (also known as Narcotine, Nectodon, Nospen, and Anarcotine) is a benzylisoquinoline alkaloid from plants of the Papaveraceae family, without significant painkilling properties. This agent is primarily used for its antitussive (cough-suppressing) effects. It has also been shown to have anticancer activity. (-)-alpha-Narcotine is found in opium poppy.

CAS Number

128-62-1

Structure

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

Synonyms

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Synonym	Source
(-)-a-Narcotine	Generator
(-)-alpha-Narcotine	ChEBI
(-)-Narcotine	ChEBI
(-)-Α-narcotine	Generator
(-)-α-narcotine	Generator
a-Narcotine	Generator
alpha-Narcotine	ChEBI
Capval	MeSH
Capval tropfen	MeSH
Coscopin	HMDB

Showing 1 to 10 of 54 entries

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C22H23NO7

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

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

Isomeric SMILES

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

Average Molecular Weight

413.4205

Monoisotopic Molecular Weight

413.147452095

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	0.3 mg/mL at 30 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Isoelectric point	Not Available
Mass Composition	C 63.92%; H 5.61%; N 3.39%; O 27.09%	DFC
Melting Point	Mp 176°	DFC
Optical Rotation	[a]D -200 (CHCl3)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(-)-alpha-Narcotine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-0090000000-32e92f98445c85eff993	Spectrum
Predicted GC-MS	(-)-alpha-Narcotine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-00di-0090000000-d382091e1ec4d8b38b31	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00di-0092000000-b90243e40af9870ee7a7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00di-0091000000-a54e072ef1d92f81334d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00di-0091000000-fce496b34ef93b8f503f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0ab9-0040900000-47e532749f5b8ffb3ccc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00di-0002900000-254fac469b3a08249319	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-0494000000-cb9d8aed31ebc22f9c22	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-03k9-0062900000-bf0cf5fac123965ac7b1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-0089300000-86a4acdf0e1666ee2f5d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-0097000000-3dc8b045aeb87b81f488	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0096200000-0e46351b9e099dd035ff	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-0097000000-2c38fbf5a5a8273cb562	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-03k9-0062900000-d48438307b64d04a2721	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0010900000-a69d344c6c2917e1894f	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0013900000-5b826e3916f6a190b5d4	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03k9-0349500000-0a1171b8ad158af511de	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f96-1938000000-0226d383a4c62f6dd51a	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0002900000-3e5155cb1df43a1ee339	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03yj-0009300000-554dd8c085d71b8e8c59	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0i6u-1109000000-3b5e0f2ae056ecae25b2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-3a2b668bf2dbd5c6416c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0007900000-6699c8e8d0e97bb3ffff	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ot-0549100000-6e0506ecee44b088751b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0010900000-def7e1eece373bfc3cb7	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0031900000-3d606db82b215faa9e7e	2021-09-25	View Spectrum