ChemFOnt: Showing chemical card for Physcion (CFc000335961)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:28:49 UTC

Chemfont ID

CFc000335961

Molecule Identification

Common Name

Physcion

Definition

Physcion, also known as emodin monomethyl ether or parienin, is a member of the class of compounds known as anthraquinones. Anthraquinones are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Physcion is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Physcion can be synthesized from 2-methylanthraquinone. Physcion can also be synthesized into torososide B and physcion 8-gentiobioside. Physcion can be found in common sage, garden rhubarb, and sorrel, which makes physcion a potential biomarker for the consumption of these food products. Physcion has also been shown to protect lichens against UV-B light, at high altitudes in Alpine regions. The UV-B light stimulates production of parietin and the parietin protects the lichens from damage. Lichens in arctic regions such as Svarlbard retain this capability though they do not encounter damaging levels of UV-B, a capability that could help protect the lichens in case of Ozone layer thinning .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,8-Dihydroxy-3-methoxy-6-methyl-9,10-anthracenedione	ChEBI
1,8-Dihydroxy-3-methoxy-6-methylanthraquinone	ChEBI
1,8-Dihydroxy-3-methyl-6-methoxyanthraquinone	ChEBI
Emodin monomethyl ether	ChEBI
Parienin	ChEBI
Parietin	ChEBI
Physcione	ChEBI
Rheochrysidin	ChEBI
Emodin 3-methyl ether	MeSH

Chemical Formula

C₁₆H₁₂O₅

Average Molecular Weight

284.2635

Monoisotopic Molecular Weight

284.068473494

IUPAC Name

1,8-dihydroxy-3-methoxy-6-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

physcion

CAS Registry Number

521-61-9

SMILES

COC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(C)C=C1O)C2=O

InChI Identifier

InChI=1S/C16H12O5/c1-7-3-9-13(11(17)4-7)16(20)14-10(15(9)19)5-8(21-2)6-12(14)18/h3-6,17-18H,1-2H3

InChI Key

FFWOKTFYGVYKIR-UHFFFAOYSA-N

Chemical Taxonomy

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

Anthraquinone
9,10-anthraquinone
Aryl ketone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
Ketone
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Anthraquinone type (C17045 )

Functional Ontology

Not Available

Exogenous (FooDB: )

Food

Herb and spice

Herb

Sorrel (FooDB: FOOD00164)
Common sage (FooDB: FOOD00165)

Vegetable

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

Process

Not Available

Role

Biological role

Calcium antagonist (FooDB: )
Anti septic (FooDB: )
Cathartic (FooDB: )
Purgative (FooDB: )

Industrial application

Agriculture

Pesticide (FooDB: )

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.087 g/L	ALOGPS
logP	2.95	ALOGPS
logP	3.97	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.89	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.62 m³·mol⁻¹	ChemAxon
Polarizability	28.69 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon