Structure Database (LMSD)

Common Name
Moronic acid
Systematic Name
3-oxoolean-18-en-28-oic acid
Synonyms
LM ID
LMPR0106150002
Formula
C30H46O3
Exact Mass
Calculate m/z
454.344696
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

Moronic acid is a triterpenoid that has been found in M. euosma and has diverse biological activities.1,2,3,4 It inhibits α-glucosidase and α-amylase (IC50s = 10.57 and 20.08 µg/ml, respectively).1 Moronic acid inhibits the replication of HIV-1 in H9 T cells (EC50 = <0.1 µg/ml).2 It decreases intestinal macrophage infiltration and the levels of Tnf-α, Il-6, and Il-1β in a mouse model of chronic colitis induced by the sulfated polysaccharide dextran sulfate (DSS).3 Moronic acid inhibits ear edema induced by the PKC activator 12-O-tetradecanoylphorbol-13-acetate (TPA) in mice (ID50 = 379 nmol/ear). It also reduces the number of tumors per mouse and the percentage of mice with tumors in a two-stage mouse skin model of tumor formation initiated and promoted by the polycyclic aromatic hydrocarbon (PAH) 7,12-dimethylbenz[a]anthracene (DMBA) and TPA, respectively.4

This information has been provided by Cayman Chemical

References

1. Koki, M., Yalo, M., Makhaba, M., et al. Phytochemical investigation and biological studies on selected Searsia species. Plants (Basel) 11(20), 2793 (2022).
1. Koki, M., Yalo, M., Makhaba, M., et al. Phytochemical investigation and biological studies on selected Searsia species. Plants (Basel) 11(20), 2793 (2022).
2. Ito, J., Chang, F.R., Wang, H.K., et al. Anti-AIDS agents. 48.(1) Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian propolis. J. Nat. Prod. 64(10), 1278-1287 (2001).
2. Ito, J., Chang, F.R., Wang, H.K., et al. Anti-AIDS agents. 48.(1) Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian propolis. J. Nat. Prod. 64(10), 1278-1287 (2001).
3. Ruan, S. Moronic acid improves intestinal inflammation in mice with chronic colitis by inhibiting intestinal macrophage polarization. J. Biochem. Mol. toxicol. 36(11), e23188 (2022).
3. Ruan, S. Moronic acid improves intestinal inflammation in mice with chronic colitis by inhibiting intestinal macrophage polarization. J. Biochem. Mol. toxicol. 36(11), e23188 (2022).
4. Yasukawa, K., Yu, S.Y., Tsutsumi, S., et al. Inhibitory effects of Brazilian propolis on tumor promotion in two-stage mouse skin carcinogenesis. J. Pharm. Nutr. Sci. 2(1), 71-76 (2012).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Ozoroa mucronata (#1158814)
Magnoliopsida (#3398)
Moronic acid, a simple triterpenoid keto acid with antimicrobial activity isolated from Ozoroa mucronata.,
Planta Med, 1979
Pubmed ID: 538108

String Representations

InChiKey (Click to copy)
UMYJVVZWBKIXQQ-QALSDZMNSA-N
InChi (Click to copy)
InChI=1S/C30H46O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h18-19,21-22H,8-17H2,1-7H3,(H,32,33)/t19-,21+,22-,27+,28-,29-,30+/m1/s1
SMILES (Click to copy)
C1CC(=O)C(C)(C)[C@]2([H])CC[C@@]3(C)[C@@]4(C)[C@@]([H])(C5[C@](C(=O)O)(CCC(C)(C)C=5)CC4)CC[C@]3([H])[C@@]12C

Other Databases

Wikipedia
Moronic_acid
CHEBI ID
30815
PubChem CID
489941
Cayman ID
30654

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 5
Aromatic Rings 0
Rotatable Bonds 1
Van der Waals Molecular Volume 484.21
Topological Polar Surface Area 54.37
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 7.44
Molar Refractivity 131.68

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Created at
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Updated at
4th Apr 2024