Structure Database (LMSD)

Common Name
Gypsogenic acid
Systematic Name
3β-hydroxyolean-12-ene-23,28-dioic acid
Synonyms
LM ID
LMPR0106150032
Formula
C30H46O5
Exact Mass
Calculate m/z
486.334525
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C30 isoprenoids (triterpenes) [PR0106]
Oleanane triterpenoids [PR010615]

Biological Context

Gypsogenic acid is a triterpene acid that has been found in M. stenostachya and has antibacterial and trypanocidal activities.1,2 It is active against the oral bacterial pathogens E. faecalis, S. salivarius, S. sanguinis, S. mitis, S. mutans, and S. sobrinus (MICs = 50-200 µg/ml).1 Gypsogenic acid induces lysis of T. cruzi in isolated mouse blood (IC50 = 56.6 µM).2

This information has been provided by Cayman Chemical

References

1. Cunha, L.C.S., e Silva, M.L.A., Furtado, N.A.J.C., et al. Antibacterial activity of triterpene acids and semi-synthetic derivatives against oral pathogens. Z. Naturforsch. C. J. Biosci. 62(9-10), 668-672 (2007).
2. Cunha, W.R., Martins, C.H., da Silva, F., D., et al. In vitro trypanocidal activity of triterpenes from Miconia species. Planta Med. 69(5), 470-472 (2003).

String Representations

InChiKey (Click to copy)
PAIBKVQNJKUVCE-JUENUIDLSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
OC([C@]12CCC(C[C@@]1([H])C1[C@@](C)(CC2)[C@@]2(C)[C@]([H])(CC=1)[C@]1(C)[C@@]([H])(CC2)[C@@](C(=O)O)(C)[C@@H](O)CC1)(C)C)=O

Other Databases

CHEBI ID
71531
PubChem CID
15560324
Cayman ID
36025

Calculated Physicochemical Properties

Heavy Atoms 35
Rings 5
Aromatic Rings 0
Rotatable Bonds 2
Van der Waals Molecular Volume 501.79
Topological Polar Surface Area 94.83
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 6.58
Molar Refractivity 135.16

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Updated at
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