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Ganoderic Acid A

HCID 471002
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Basic information

CAS
81907-62-2
Standard SMILES
C[C@H](CC(=O)C[C@@H](C)[C@H]1C[C@H](O)[C@@]2(C)C3=C(C(=O)C[C@]12C)[C@@]1(C)CCC(=O)C(C)(C)[C@@H]1C[C@@H]3O)C(=O)O
InChIKey
DYOKDAQBNHPJFD-JNTBEZBXSA-N
Molecular formula
C30H44O7
Average molar mass
516.7 g/mol
Monoisotopic mass
516.30870374

Overview

Ganoderic acid A is a triterpenoid.

Names & identifiers

Preferred name
Ganoderic Acid A
IUPAC
(2R,6R)-6-[(5R,7S,10S,13R,14R,15S,17R)-7,15-dihydroxy-4,4,10,13,14-pentamethyl-3,11-dioxo-2,5,6,7,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoic acid
English name
Ganoderic acid A
Molecular formula
C30H44O7
Molecular weight
516.67

Names & synonyms

Ganoderic acid A81907-62-2548G37DF65(2R,6R)-6-[(5R,7S,10S,13R,14R,15S,17R)-7,15-dihydroxy-4,4,10,13,14-pentamethyl-3,11-dioxo-2,5,6,7,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoic acidDTXSID80903984Lanost-8-en-26-oic acid, 7,15-dihydroxy-3,11,23-trioxo-, (7beta,15alpha,25R)-(25R)-3,11,23-trioxo-7beta,15alpha-dihydroxy-lanost-8-ene-26-oic acid(2R,6R)-6-((5R,7S,10S,13R,14R,15S,17R)-7,15-dihydroxy-4,4,10,13,14-pentamethyl-3,11-dioxo-2,5,6,7,12,15,16,17-octahydro-1H-cyclopenta(a)phenanthren-17-yl)-2-methyl-4-oxoheptanoic acidRefChem:37018DTXCID401331919Ganoderic-acid-AMFCD26131275
Show more names
(2R,6R)Aids070759Aids-070759Ganoderic acid A-RMGanoderic acid A, >98%Ganoderic acid A (Standard)-6-((7S,10S,13R,14R,15S,17R)-2-methyl-4-oxoheptanoic acid
C30H44O7Lanost-8-en-26-oic acid, 7,15-dihydroxy-3,11,23-trioxo-, (7.beta.,15.alpha.,25R)-(2R,6R)-6-[(5R,7S,10S,13R,14R,15S,17R)-7,15-dihydroxy-4,4,10,13,14-pentamethyl-3,11-dioxo-2,5,6,7,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxo-heptanoic acidCHEMBL602899UNII-548G37DF65(7ss,15a,25R)-7,15-Dihydroxy-3,11,23-trioxo-lanost-8-en-26-oic Acid; Ganoderic acid A(25R)-7beta,15alpha-Dihydroxy-3,11,23-trioxo-5alpha-lanost-8-en-26-oic acidganoderic acid a(p)

Properties

Computed structural properties

XLogP
2.2
Topological polar surface area
129 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
7
Rotatable bonds
6
Heavy atoms
37
Formal charge
0
Complexity
1,070

Experimental & physicochemical properties

LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]

Physicochemical properties

Melting point
118 · 118~123℃
Boiling point
690.1 · 690.1±55.0 °C(Predicted)
Density
1.22 · 1.22
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C
solubility
Chloroform (Slightly, Sonicated), Methanol (Slightly)
form
Solid
pka
4.78 · 4.78±0.23(Predicted)
color
White to Pale Yellow
Major Application
metabolomicsvitamins, nutraceuticals, and natural products
InChIKey
OVUOUFPIPZJGME-YYJACZGBNA-N
SMILES
[C@@]12(C)[C@@H](O)C[C@H](/C(/C)=C/C(=O)CC(C)C(O)=O)[C@@]1(C)CC(=O)C1[C@@]3([C@]([H])(C(C)(C)C(CC3)=O)C[C@H](O)C2=1)C |&1:0,2,5,17,23,24,34,r|

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
WGK 3
hs_code
29189900
safety_code
24/25
Storage Class
11 - Combustible Solids

Chemistry & industry

Applications · 2 items

DescriptionGanoderic acid A is a triterpene that has been found in Ganoderma and has diverse biological activities. It reduces cell viability, expression of superoxide dismutase 1 (SOD1), SOD2, and SOD3, and production of reactive oxygen species (ROS) in PC3 prostate cancer cells. Ganoderic acid A (2-100 μg/ml) reduces hypoxia-induced apoptosis in H9c2 cardiomyocytes. It inhibits LPS-induced activation of NF-κB, release of TNF-α, IL-1β, and IL-6, and mitochondrial activity in primary mouse cortical microglia. Ganoderic acid A (20 and 40 mg/kg) reduces lung myeloperoxidase (MPO) activity, neutrophil infiltration, and NF-κB signaling, as well as bronchoalveolar lavage fluid (BALF) levels of TNF-α, IL-1β, and IL-6 in a mouse model of LPS-induced lung injury. It also reduces weight gain and hepatic lipid accumulation and improves insulin sensitivity in a mouse model of high-fat diet-induced obesity.

UsesGanoderic Acid A, is a new lanostanoid triterpene extracted from the fruit bodies of Ganoderma Lucidum mushroom. these compounds are shown to possess many therapeutic properties. They can be used as anti-virus, anti-inflammation, anti-tumor, immunity-promoting, anti-diabetic, etc.

Additional notes

DefinitionChEBI: Ganoderic acid A is a triterpenoid.

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
81907-62-2
PubChem CID
471002
DTXSID
DTXSID80903984
ChEMBL
CHEMBL602899
ChEBI
CHEBI:168262
UNII
548G37DF65
Nikkaji
J39.404A
FDA UNII
548 G37DF65 · 548G37DF65
UNSPSC Code
41116107 · 41116107
NACRES
25 · NA.25
Safety Statements
24 · 24/25
WGK Germany
3 · WGK 3
HS Code
29189900 · 29189900
Storage Class
11 · 11 - Combustible Solids