ChemFOnt: Showing chemical card for Salvianolic acid K (CFc000282462)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:50 UTC

Chemfont ID

CFc000282462

Molecule Identification

Common Name

Salvianolic acid K

Definition

Salvianolic acid K, also known as salvianolate K, is a member of the class of compounds known as lignans, neolignans and related compounds. Lignans, neolignans and related compounds are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9¬¥ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. Salvianolic acid K is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Salvianolic acid K can be found in common sage, which makes salvianolic acid K a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-{4-[(1E)-3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoate	Generator
Salvianolate K	Generator

Chemical Formula

C₂₇H₂₄O₁₃

Average Molecular Weight

556.4717

Monoisotopic Molecular Weight

556.121690854

IUPAC Name

2-{4-[(1E)-3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

Traditional Name

2-{4-[(1E)-3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

CAS Registry Number

None

SMILES

OC(C(OC1=CC=C(\C=C\C(=O)OC(CC2=CC=C(O)C(O)=C2)C(O)=O)C=C1O)C(O)=O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C27H24O13/c28-16-5-1-14(10-18(16)30)11-22(26(35)36)39-23(33)8-3-13-2-7-21(20(32)9-13)40-25(27(37)38)24(34)15-4-6-17(29)19(31)12-15/h1-10,12,22,24-25,28-32,34H,11H2,(H,35,36)(H,37,38)/b8-3+

InChI Key

AZOCLKLJIKZOLF-FPYGCLRLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Neolignan skeleton
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Phenoxyacetate
3-phenylpropanoic-acid
Tricarboxylic acid or derivatives
Catechol
Phenoxy compound
Phenol ether
Styrene
Sugar acid
Phenol
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Ether
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic alcohol
Organic oxide
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302946)

Food

Herb and spice

Herb

Common sage (FooDB: FOOD00165)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.037 g/L	ALOGPS
logP	3.11	ALOGPS
logP	3.33	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	2.81	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	231.51 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	135.8 m³·mol⁻¹	ChemAxon
Polarizability	53.11 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

External Links

HMDB ID

HMDB0302946

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007006

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Salvianolic acid K (CFc000282462)

MOL for CFc000282462 (Salvianolic acid K)

3D MOL for CFc000282462 (Salvianolic acid K)

3D SDF for CFc000282462 (Salvianolic acid K)

3D-SDF for CFc000282462 (Salvianolic acid K)

PDB for CFc000282462 (Salvianolic acid K)

3D PDB for CFc000282462 (Salvianolic acid K)

SMILES for CFc000282462 (Salvianolic acid K)

INCHI for CFc000282462 (Salvianolic acid K)

Structure for CFc000282462 (Salvianolic acid K)

3D Structure for CFc000282462 (Salvianolic acid K)