U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry MIXED
Molecular Formula C22H40O7
Molecular Weight 416.5488
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AGARICIC ACID

SMILES

CCCCCCCCCCCCCCCCC(C(O)=O)C(O)(CC(O)=O)C(O)=O

InChI

InChIKey=HZLCGUXUOFWCCN-UHFFFAOYSA-N
InChI=1S/C22H40O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18(20(25)26)22(29,21(27)28)17-19(23)24/h18,29H,2-17H2,1H3,(H,23,24)(H,25,26)(H,27,28)

HIDE SMILES / InChI

Molecular Formula C22H40O7
Molecular Weight 416.5488
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created using several sources including: http://doctorschar.com/agaric-fomitopsis-officinalis/; http://www.drugfuture.com/chemdata/agaricic-acid.html; https://www.ncbi.nlm.nih.gov/pubmed/5249940; https://www.ncbi.nlm.nih.gov/pubmed/5721536; https://www.ncbi.nlm.nih.gov/pubmed/5781578; https://www.ncbi.nlm.nih.gov/pubmed/17508207; https://www.ncbi.nlm.nih.gov/pubmed/17163944

Agaricic acid is a resin acid that obtained by extraction with alcohol from obtained from various fungus plants (mushroom) such as Polyporus officinalis (a wood-decay fungus). Since the late 19th century it was used as an antipyretic and antiperspirant, and was official in the German Pharmacopoeia under the name of Agaricinum. Agaricic acid is a sesquihydrate, odorless, almost tasteless, crystalline powder, little soluble in cold water. It is irritant to the gastro-intestinal tract. Experiments on the synthesis of agaricic acid as well as studies of its pharmacological properties are known since 1960s. It was found that Agaricic acid was highly inhibitory (50 to 100%) to malic and alpha-glycerophosphate dehydrogenases of the insect trypanosomatid, Crithidia fasciculata. Agaricic acid is a mycotoxin and is considered under regulations and guidelines established in European Union to protect the consumer from the harmful effects mycotoxins in food. Agaricic acid is among the newest agents to function in the treatment of wrinkles: it inhibits the cross-linking process which leads to dermal proteins denaturation.

CNS Activity

Curator's Comment: Depresses the nervous, respiratory, and circulatory systems in animals. Owing to its power over the sympathetic and spinal nervous system, certain cases of epilepsy and chorea have been controlled by it; in neuralgia and insanity it has been found of value where nutrition was imperfect and the cerebral circulation feeble.

Originator

Curator's Comment: Jahns, in 1883, isolated agaric acid from the alcoholic extract of the fungus, for which he found the formula. The formula and the bi-basic nature of the acid was confirmed by Schmieder, in 1886, who made an exhaustive study of the chemistry of this fungus.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Pharmacologic study of norcaperatic and agaricic acids.
1967 Dec
Agaric acid.
1981
Agaric acid induces mitochondrial permeability transition through its interaction with the adenine nucleotide translocase. Its dependence on membrane fluidity.
2005 Aug
The effect of N-ethylmaleimide on permeability transition as induced by carboxyatractyloside, agaric acid, and oleate.
2008
Patents

Patents

Sample Use Guides

Tincture of boletus, 1 to 5 drops; specific boletus, fraction of a drop to 5 drops; agaricin, 1/16 to ⅓ grain.
Route of Administration: Oral
In Vitro Use Guide
Agaricic acid inhibited 50% growth of of the insect trypanosomatid, Crithidia fasciculata at 7 mM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:13:49 GMT 2023
Edited
by admin
on Fri Dec 15 15:13:49 GMT 2023
Record UNII
2XE342S7L6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AGARICIC ACID
MI  
Common Name English
AGARICIC ACID, (±)-
Common Name English
AGARIC ACID [MART.]
Common Name English
LARICIC ACID
Common Name English
.ALPHA.-CETYLCITRIC ACID
Common Name English
Agaric acid [WHO-DD]
Common Name English
AGARICIC ACID [MI]
Common Name English
AGARIC ACID
MART.   WHO-DD  
Common Name English
AGARICINUM [HPUS]
Common Name English
(±)-AGARICIC ACID
Common Name English
NSC-65690
Code English
AGARICINUM
HPUS  
Common Name English
2-HYDROXY-1,2,3-NON-DECANETRICARBOXLIC ACID
Common Name English
N-HEXADECYLCITRIC ACID
Common Name English
AGARICINIC ACID
Common Name English
NSC-60429
Code English
AGARICIN
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C471
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
211-566-5
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
PRIMARY
NSC
65690
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
PRIMARY
DAILYMED
2XE342S7L6
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
PRIMARY
MESH
C011396
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
PRIMARY
NCI_THESAURUS
C83523
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
PRIMARY
RXCUI
1441428
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
PRIMARY RxNorm
EVMPD
SUB12749MIG
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
PRIMARY
CAS
666-99-9
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
PRIMARY
PUBCHEM
12629
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
PRIMARY
FDA UNII
2XE342S7L6
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
PRIMARY
MERCK INDEX
m1448
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
PRIMARY Merck Index
SMS_ID
100000077982
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID2046705
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
PRIMARY
WIKIPEDIA
Agaric acid
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
PRIMARY
NSC
60429
Created by admin on Fri Dec 15 15:13:49 GMT 2023 , Edited by admin on Fri Dec 15 15:13:49 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY