Showing Compound 6''-(4-Hydroxycinnamoyl)astragalin (FDB002430)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:22 UTC

Update date

2019-11-26 02:57:26 UTC

Primary ID

FDB002430

Secondary Accession Numbers

FDB020488

Chemical Information

FooDB Name

6''-(4-Hydroxycinnamoyl)astragalin

Description

Kaempferol 3-(6''-p-coumaroylgalactoside) is a member of the class of compounds known as flavonoid 3-o-p-coumaroyl glycosides. Flavonoid 3-o-p-coumaroyl glycosides are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Kaempferol 3-(6''-p-coumaroylgalactoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Within the cell, kaempferol 3-(6''-p-coumaroylgalactoside) is primarily located in the membrane (predicted from logP).

CAS Number

20316-62-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Kaempferol 3-(6-P-coumaroylgalactoside)	HMDB
(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid	Generator
6''-(4-Hydroxycinnamoyl)astragalin	manual
6''-O-(4-Hydroxycinnamoyl)astragalin	manual
Potengriffioside a	biospider
Tiliroside	db_source
Tribuloside	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	2.97	ALOGPS
logP	2.89	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	6.43	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	212.67 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	148.84 m³·mol⁻¹	ChemAxon
Polarizability	57.63 Å³	ChemAxon
Number of Rings	5	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

C30H26O13

IUPAC name

(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

InChI Identifier

InChI=1S/C30H26O13/c31-16-6-1-14(2-7-16)3-10-22(35)40-13-21-24(36)26(38)27(39)30(42-21)43-29-25(37)23-19(34)11-18(33)12-20(23)41-28(29)15-4-8-17(32)9-5-15/h1-12,21,24,26-27,30-34,36,38-39H,13H2/b10-3+

InChI Key

DVGGLGXQSFURLP-XCVCLJGOSA-N

Isomeric SMILES

OC1C(COC(=O)\C=C\C2=CC=C(O)C=C2)OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(O)C1O

Average Molecular Weight

594.5196

Monoisotopic Molecular Weight

594.137340918

Classification

Description

Belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 3-O-p-coumaroyl glycosides

Alternative Parents

Substituents

Flavonoid 3-o-6-p-coumaroyl-glycoside
Flavonoid-3-o-glycoside
Flavone
Hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Chromone
O-glycosyl compound
Glycosyl compound
Benzopyran
1-benzopyran
Styrene
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Pyran
Monosaccharide
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Food

Biological:

Plant

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 60.61%; H 4.41%; O 34.98%	DFC
Melting Point	Mp 269-271° (267-269°)	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]24D +69.9 (c, 0.1 in MeOH)	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	6''-(4-Hydroxycinnamoyl)astragalin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00mk-4983240000-99127f52bd6fe47f3408	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000b-3923203000-dc4ba29827e830ac19e9	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, "6''-O-p-Coumaroyltrifolin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6''-(4-Hydroxycinnamoyl)astragalin, TMS_2_16, 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	splash10-000j-0490350000-c0911ae64c00bc067138	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0290000000-f9ea658e54cfef4e8836	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05n0-0890000000-86dd969d4d72d7ed325b	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01p5-0940140000-b9a14cb7eb5dcc60c4d0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01pa-0960100000-e363837065830c134fd2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01p9-1970000000-f29307b10bfd0c35cf41	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000090000-15ecfa4fbd57c3fda14c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0300090000-98778e740dfb4359cb67	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0i0c-1910120000-87e191879fbe35671d70	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000090000-9dd92b4536db782e86cc	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0000090000-9ca20b1493104fdb742e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxs-1900140000-ae23fa2401edb5134264	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5320686

Pubchem Substance ID

Not Available

ChEBI ID

604269

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

KRH29-Q:CLT15-R

EAFUS ID

Not Available

Dr. Duke ID

TILIROSIDE

BIGG ID

Not Available

KNApSAcK ID

C00005851

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
Anti HIV	22587	An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.	DUKE
Diaphoretic		An agent that induces perspiration, playing a biological role in thermoregulation. Therapeutically, it's used to treat fever, detoxify, and relieve congestion. Key medical uses include managing hyperthermia, aiding in toxin removal, and alleviating symptoms of colds and flu.	DUKE
Protisticide		An agent that kills protozoans, used as a herbicide or in therapeutic applications to treat protozoan infections, with key medical uses including managing parasitic diseases and infections.	DUKE