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Gypsogenic acid

CAT: 0804-HY-W587957-01Size: 500 µgDry Ice: NoHazardous: No
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CAT#:0804-HY-W587957-01Size:500 µg
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Description
Gypsogenic acid is a triterpenoid acid that can be isolated from Miconia stenostachya and has antibacterial and trypanoidal activities. The MICs values of Gypsogenic acid for the oral bacterial pathogens Enterococcus faecalis, Streptococcus salivarius, Streptococcus haematococcus, Streptococcus mutans and sobrinus were 50-200 μg/mL. Gypsogenic acid can induce blood cortensite cleavage in isolated mice with IC50 56.6 μM[1][2].
CAS Number
5143-05-5
UNSPSC
12352211
Hazard Statement
H302, H315, H319, H335
Target
Bacterial; Parasite
Type
Reference compound
Related Pathways
Anti-infection
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/gypsogenic-acid.html
Purity
99.9
Smiles
C[C@@]12C([C@@]3([H])[C@@](CC2)(CCC(C)(C3)C)C(O)=O)=CC[C@@]4([H])[C@]1(CC[C@]5([H])[C@@]4(CC[C@@H]([C@@]5(C)C(O)=O)O)C)C
Molecular Formula
C30H46O5
Molecular Weight
486.68
Precautions
H302, H315, H319, H335
References & Citations
[1]Scalon Cunha LC, et al. Antibacterial activity of triterpene acids and semi-synthetic derivatives against oral pathogens. Z Naturforsch C J Biosci. 2007 Sep-Oct;62 (9-10) :668-72.|[2]Cunha WR, et al. In vitro trypanocidal activity of triterpenes from miconia species. Planta Med. 2003 May;69 (5) :470-2.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Gypsogenic acid

Gypsogenic acid is a pentacyclic triterpenoid that is olean-12-ene substituted by carboxy groups at positions 23 and 28 and a hydroxy group at position 3 (the 3beta stereoisomer). It has a role as a metabolite and an antibacterial agent. It is a hydroxy carboxylic acid and a pentacyclic triterpenoid. It is a conjugate acid of a gypsogenate(2-). It derives from a hydride of an oleanane.

CAS Number5143-05-5
PubChem CID15560324
IUPAC Name(3S,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-3-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
Molecular FormulaC30H46O5
Molecular Weight486.7
XLogP6.7
Topological Polar Surface Area94.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Heavy Atom Count35
Formal Charge0
Complexity983
SMILES
C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)C(=O)O)O
InChI
InChI=1S/C30H46O5/c1-25(2)13-15-30(24(34)35)16-14-27(4)18(19(30)17-25)7-8-20-26(3)11-10-22(31)29(6,23(32)33)21(26)9-12-28(20,27)5/h7,19-22,31H,8-17H2,1-6H3,(H,32,33)(H,34,35)/t19-,20+,21+,22-,26+,27+,28+,29-,30-/m0/s1
InChIKey
PAIBKVQNJKUVCE-JUENUIDLSA-N
Chemical Structure
2D Structure
2D structure of Gypsogenic acid
CAS: 5143-05-5
CID: 15560324
Formula: C30H46O5
MW: 486.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight486.7
XLogP36.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass486.33452456
Monoisotopic Mass486.33452456
Topological Polar Surface Area94.8 Ų
Heavy Atom Count35
Formal Charge0
Complexity983
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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