Limonyl acetate - Compound Card

Limonyl acetate

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Limonyl acetate

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles CC(=O)O[C@@H]1C[C@H]2C(C)(C)O[C@@H]3[C@@]2([C@@H]2[C@@]1(C)[C@@]14O[C@@H]1C(=O)O[C@H]([C@@]4(CC2)C)c1cocc1)COC(=O)C3
InChI InChI=1S/C28H34O9/c1-14(29)34-18-10-17-24(2,3)36-19-11-20(30)33-13-27(17,19)16-6-8-25(4)21(15-7-9-32-12-15)35-23(31)22-28(25,37-22)26(16,18)5/h7,9,12,16-19,21-22H,6,8,10-11,13H2,1-5H3/t16-,17-,18+,19-,21-,22+,25-,26+,27+,28+/m0/s1
InChIKey WQDRZTIUAGZBQW-MYNUBWEDSA-N
Formula C28H34O9
HBA 9
HBD 0
MW 514.57
Rotatable Bonds 2
TPSA 113.8
LogP 3.5
Number Rings 7
Number Aromatic Rings 1
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 514.22
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Vepris glomerata Rutaceae Plantae 2695416
2 Vepris glomerata Rutaceae Plantae 2695416
3 Vepris uguenensis Rutaceae Plantae 2695421
4 Vepris uguenensis Rutaceae Plantae 2695421

Showing of synonyms

  • Kiplimo JJ, Koorbanally NA. (2012). Antibacterial activity of an epoxidised prenylated cinnamaldehdye derivative from Vepris glomerata. Phytochemistry Letters,2012,5(3),438-442. [View] [PubMed]
  • Kiplimo JJ, Shahidul Islam M, et al. (2012). Ring A-seco limonoids and flavonoids from the Kenyan Vepris uguenensis Engl. and their antioxidant activity. Phytochemistry,2012,83(2012),136-143. [View] [PubMed]
  • Kiplimo JJ, Koorbanally NA. (2012). The phytochemistry and biological activity of secondary metabolites from Kenyan Vernonia and Vepris species. PhD Thesis, University of Kwazulu-Natal, South Africa,2012. [View] [PubMed]
Pubchem: 101211607

No compound-protein relationship available.

Structure

SMILES: c1occc1C(OC(=O)C(C234)O4)C3CCC5C67C(CCC25)COC6CC(=O)OC7

Level: 1

Mol. Weight: 514.57 g/mol

Structure

SMILES: C123C(O3)C(=O)OCC2CCC4C56C(CCC14)COC5CC(=O)OC6

Level: 0

Mol. Weight: 514.57 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 514.57 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-5.24
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.12
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.42

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.57
Plasma Protein Binding
48.14
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.11
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.48
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.32
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.19
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1373.15
Rat (Acute)
5.03
Rat (Chronic Oral)
1.94
Fathead Minnow
5.55
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
484.16
Hydration Free Energy
-2.84
Log(D) at pH=7.4
2.47
Log(P)
2.32
Log S
-5.98
Log(Vapor Pressure)
-9.29
Melting Point
233.84
pKa Acid
4.55
pKa Basic
4.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7882
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7882
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7787
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7787
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7656
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7656
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7578
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7578
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7451
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7451
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7399
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7399
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7370
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7370
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7357
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7357
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7266
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7266
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7263
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7263
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7262
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7262
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7260
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7260
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7217
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7217
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7209
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7209
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7148
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7148
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7148
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7148
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 2 0.7117
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 2 0.7117
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7087
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7087
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7064
Matrix metalloproteinase-20 O60882 MMP20_HUMAN Homo sapiens 2 0.7064
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7064
Matrix metalloproteinase-20 O60882 MMP20_HUMAN Homo sapiens 2 0.7064
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7058
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7058
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7029
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7029

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