AFCDB: Orientin (FDB002510)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:24 UTC

Update date

2020-02-24 19:10:31 UTC

Primary ID

FDB002510

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Orientin

Description

Orientin belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Orientin has been detected, but not quantified in, several different foods, such as flour, wild rice (Zizania), corns (Zea mays), fenugreeks (Trigonella foenum-graecum), and quinoas (Chenopodium quinoa). This could make orientin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Orientin.

CAS Number

28608-75-5

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	2.18 g/L	ALOGPS
logP	0.34	ALOGPS
logP	-0.35	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	6.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	197.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	108.01 m³·mol⁻¹	ChemAxon
Polarizability	42.33 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H20O11

IUPAC name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

InChI Identifier

InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2

InChI Key

PLAPMLGJVGLZOV-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(C(O)C(O)C1O)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC(O)=C(O)C=C1

Average Molecular Weight

448.3769

Monoisotopic Molecular Weight

448.100561482

Classification

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
C-glycosyl compound
Chromone
1-benzopyran
Benzopyran
Catechol
Phenol
Pyranone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 56.25%; H 4.50%; O 39.25%	DFC
Melting Point	Mp 265-267° dec.	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]20D +18.4 (c, 1.4 in Py)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Orientin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-5359500000-f9adac53dffd9a9c99e7	Spectrum
Predicted GC-MS	Orientin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udm-2400649000-74ca092951d9881de08b	Spectrum
Predicted GC-MS	Orientin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Orientin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Orientin, TMS_3_26, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Orientin, TMS_4_39, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Orientin, TMS_4_41, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Orientin, TMS_4_45, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Orientin, TMS_5_37, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Orientin, TMS_5_41, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Orientin, TMS_5_42, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Orientin, TMS_5_44, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Orientin, TMS_6_22, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Orientin, TMS_6_24, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Orientin, TMS_6_26, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Orientin, TBDMS_3_26, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Orientin, "Orientin,3TMS,#26" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - , negative	splash10-004j-0009400000-3059cfe62dc1fc2d4ae7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-002b-0139400000-f3fff996fce68da266cb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-004i-0029200000-9e20b610236551cee3e9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-001i-0940000000-6ade1586982fcaaa04d3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-002b-0007900000-299d60fdf13ab2f062f5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-002b-0007900000-db4be8b974f6d2f16d68	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-004j-0029200000-1d510f55b44dccbf2f0c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-001i-0930000000-7ba47734d755fe6187d6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-002b-0007900000-9af7a501987a53fa1186	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-001i-0930000000-1eb6b2cd4ec3df0a2991	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-004i-0029200000-daa29aee5f2e91989929	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-004j-0298000000-34defc81a94142eeadb5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-004j-0197000000-69a0d730bb6b380cf4ee	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-004j-0029200000-e3ead7f8fd2f272918ff	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-002b-0297000000-e1e2a2699aa7c4a528bf	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-0000900000-dbaba69a1ec2e196894c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01pk-3321900000-58f0bdc82c44d422ce9b	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bta-4298000000-6aa6da44ac805b909fae	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0011900000-11759d86677ab5572af7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00bj-8348900000-5afe26ef74613ffacf3c	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9443000000-3dafb42d1ba4e7e09433	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000900000-e34b057bc120eef7d6a0	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0000900000-578e80e06a8f791630d8	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-0955400000-d57d92c5c589d52431dc	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000900000-6cdaf2bc31caca882f1d	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4529887

ChEMBL ID

Not Available

KEGG Compound ID

C10114

Pubchem Compound ID

5382105

Pubchem Substance ID

Not Available

ChEBI ID

7781

Phenol-Explorer ID

255

DrugBank ID

Not Available

HMDB ID

HMDB30614

CRC / DFC (Dictionary of Food Compounds) ID

CMF48-S:CMF48-S

EAFUS ID

Not Available

Dr. Duke ID

ORIENTIN

BIGG ID

Not Available

KNApSAcK ID

C00001078

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

Orientin

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
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
cAMP-phosphodiesterase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	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

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Orientin (FDB002510)

Structure for FDB002510 (Orientin)