AFCDB: Hordatine B (FDB002328)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:20 UTC

Update date

2020-02-24 19:10:29 UTC

Primary ID

FDB002328

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Hordatine B

Description

Hordatine B belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Hordatine B has been detected, but not quantified in, a few different foods, such as barleys (Hordeum vulgare), breakfast cereal, and cereals and cereal products. This could make hordatine b a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Hordatine B.

CAS Number

10502-21-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.049 g/L	ALOGPS
logP	1.22	ALOGPS
logP	-0.2	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	12.42	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	220.69 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	181.43 m³·mol⁻¹	ChemAxon
Polarizability	62.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C29H40N8O5

IUPAC name

N-(4-carbamimidamidobutyl)-5-[(1Z)-2-[(4-carbamimidamidobutyl)carbamoyl]eth-1-en-1-yl]-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxamide

InChI Identifier

InChI=1S/C29H40N8O5/c1-41-22-17-18(6-11-23(39)34-12-2-4-14-36-28(30)31)16-21-24(27(40)35-13-3-5-15-37-29(32)33)25(42-26(21)22)19-7-9-20(38)10-8-19/h6-11,16-17,24-25,38H,2-5,12-15H2,1H3,(H,34,39)(H,35,40)(H4,30,31,36)(H4,32,33,37)/b11-6-

InChI Key

LRLXAXGCQUOKIO-WDZFZDKYSA-N

Isomeric SMILES

COC1=C2OC(C(C(=O)NCCCCNC(N)=N)C2=CC(\C=C/C(=O)NCCCCNC(N)=N)=C1)C1=CC=C(O)C=C1

Average Molecular Weight

580.6785

Monoisotopic Molecular Weight

580.31216643

Classification

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Neolignan skeleton
Benzofuran
Coumaran
Anisole
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Guanidine
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Oxacycle
Organoheterocyclic compound
Carboximidamide
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Imine
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Poaceae

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 59.98%; H 6.94%; N 19.30%; O 13.78%	DFC
Melting Point	Mp 132-135° (as dipicrate)	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]23D +54 (c, 1 in H2O)	DFC
Spectroscopic UV Data	316 (e 16200) (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Hordatine B, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udi-1100920000-284d99bf43ebe9e91a23	Spectrum
Predicted GC-MS	Hordatine B, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-2100091000-0317a0296432353d04ed	Spectrum
Predicted GC-MS	Hordatine B, "Hordatine B,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TBDMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TBDMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TBDMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TBDMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hordatine B, TBDMS_1_9, 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	splash10-0059-1900150000-a403f4358983e1ec168c	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01t9-5900110000-29f36fe2735de7c324f6	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01t9-6901000000-d59e69aeb383e0f32ae3	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-1000490000-e35f5cf4883cbdd5f055	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0abj-7001980000-09bad48f7eee2d0bf289	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9102200000-92777699576c86e6c5a4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000190000-59287dc3866db0fc51f4	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01x0-0000490000-4d2ef73aebd28bd5fa8b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9005600000-c25b6afd28888d0d7727	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000090000-f4c286e94a48276042cc	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00bl-2000290000-4ff94ead834306fabf85	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-4001690000-d199a5f5106ebca64dfb	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C08308

Pubchem Compound ID

5281114

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB30459

CRC / DFC (Dictionary of Food Compounds) ID

CKG39-H:CKG39-H

EAFUS ID

Not Available

Dr. Duke ID

HORDATINE-B

BIGG ID

Not Available

KNApSAcK ID

C00001416

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
allelopathic			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Hordatine B (FDB002328)

Structure for FDB002328 (Hordatine B)