AFCDB: (S)-Dicentrine (FDB002141)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:15 UTC

Update date

2019-11-26 02:57:04 UTC

Primary ID

FDB002141

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(S)-Dicentrine

Description

(s)-dicentrine is a member of the class of compounds known as aporphines. Aporphines are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof (s)-dicentrine is practically insoluble (in water) and a very strong basic compound (based on its pKa). (s)-dicentrine can be found in barley, which makes (s)-dicentrine a potential biomarker for the consumption of this food product.

CAS Number

517-66-8

Structure

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

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.08 g/L	ALOGPS
logP	2.76	ALOGPS
logP	3.01	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	7.06	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.72 m³·mol⁻¹	ChemAxon
Polarizability	37.53 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

C20H21NO4

IUPAC name

16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaene

InChI Identifier

InChI=1S/C20H21NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3

InChI Key

YJWBWQWUHVXPNC-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC2=C(C=C1OC)C1=C3C(C2)N(C)CCC3=CC2=C1OCO2

Average Molecular Weight

339.385

Monoisotopic Molecular Weight

339.147058165

Classification

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Naphthalene
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Anisole
Aralkylamine
Alkyl aryl ether
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Oxacycle
Acetal
Ether
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Amine
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 70.78%; H 6.24%; N 4.13%; O 18.86%	DFC
Melting Point	Mp 168-169°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D +57 (c, 1 in EtOH)	DFC
Spectroscopic UV Data	305 (log e 4.23) (95% EtOH)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(S)-Dicentrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fs-0079000000-8db4ef7d343883503869	Spectrum
Predicted GC-MS	(S)-Dicentrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(S)-Dicentrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(S)-Dicentrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-1f81863145e9ffb30531	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0029000000-18a221817aeaa6f459a4	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00am-0091000000-4722e1ecc495d0883f41	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-26e8f0a6ebd0ceac8b58	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-4a39f762b3f502df7e61	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gvo-0090000000-96836bde115a621f735f	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-952964009ca467e58825	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0009000000-c196527b93bff46d8926	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1097000000-0843fef05443ced7b858	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-a9f00908271fb71883c3	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0019000000-e204e48d446354e251f2	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01p9-0095000000-97541ac35b8b324e281a	2021-10-12	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C17426

Pubchem Compound ID

101300

Pubchem Substance ID

Not Available

ChEBI ID

581347

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

CFZ32-I:CFZ34-K

EAFUS ID

Not Available

Dr. Duke ID

DICENTRINE

BIGG ID

Not Available

KNApSAcK ID

C00025658

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
anti convulsant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

(S)-Dicentrine (FDB002141)

Structure for FDB002141 ((S)-Dicentrine)