Showing Compound Chrysophanol 8-gentiobioside (FDB019094)

Record Information

Version

1.0

Creation date

2010-04-08 22:14:08 UTC

Update date

2019-11-26 03:17:05 UTC

Primary ID

FDB019094

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Chrysophanol 8-gentiobioside

Description

Chrysophanol 8-gentiobioside belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Chrysophanol 8-gentiobioside has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, herbs and spices, pulses, and robusta coffees (Coffea canephora). This could make chrysophanol 8-gentiobioside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Chrysophanol 8-gentiobioside.

CAS Number

54944-38-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	4.54 g/L	ALOGPS
logP	-0.31	ALOGPS
logP	-0.56	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.49	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	232.9 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	134.71 m³·mol⁻¹	ChemAxon
Polarizability	56.32 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

C27H30O14

IUPAC name

1-hydroxy-3-methyl-8-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione

InChI Identifier

InChI=1S/C27H30O14/c1-9-5-11-16(12(29)6-9)21(33)17-10(18(11)30)3-2-4-13(17)39-27-25(37)23(35)20(32)15(41-27)8-38-26-24(36)22(34)19(31)14(7-28)40-26/h2-6,14-15,19-20,22-29,31-32,34-37H,7-8H2,1H3

InChI Key

DFCJAHQKYCYICW-UHFFFAOYSA-N

Isomeric SMILES

CC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1OC1OC(COC3OC(CO)C(O)C(O)C3O)C(O)C(O)C1O)C2=O

Average Molecular Weight

578.5187

Monoisotopic Molecular Weight

578.163555668

Classification

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

9,10-anthraquinone
Anthraquinone
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Vinylogous acid
Ketone
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Organic oxygen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Cytoplasm

Cell and elements:

Extracellular

Role

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	Not Available
Isoelectric point	Not Available
Mass Composition	C 56.06%; H 5.23%; O 38.72%	DFC
Melting Point	Mp 168-170°	DFC
Optical Rotation	[a]D -55.2 (c, 0.29 in MeOH)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Chrysophanol 8-gentiobioside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03di-3632190000-04f9c83dbe39f989fc7f	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001r-5721139000-c60e60d1cfa61bb528ca	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, "Chrysophanol 8-gentiobioside,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Chrysophanol 8-gentiobioside, TMS_2_15, 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	splash10-0bt9-0191080000-5edcd362cc1122b9b4a4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0291100000-06ff2ab654a062acb9a9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-1590000000-e7458306a41f336b0229	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fb9-2581190000-a35ac445dcdeb71d20db	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2490020000-844563a748647b54529f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-2390000000-4e20eef9a45df76a2447	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-61a00de4d7e65428c82c	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0391110000-dc5e3306ca005c90c129	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-4690200000-074beb930eb2a918c316	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090040000-e7110d9bb5c6a85c006f	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-4090530000-d70319d5dbd774ddb76e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zfr-6291010000-fa20c46e9f1258f5e64d	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB39488

CRC / DFC (Dictionary of Food Compounds) ID

CMM74-G:LPC48-T

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

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

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Food	Content Range	Average	Reference

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Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

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

Showing Compound Chrysophanol 8-gentiobioside (FDB019094)

Structure for FDB019094 (Chrysophanol 8-gentiobioside)