Methyl uguenenoate - Compound Card

Methyl uguenenoate

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Methyl uguenenoate

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles COC(=O)C[C@@H]1OC([C@H]2[C@@]1(CO)[C@H]1CC[C@@]3([C@]4([C@@]1(C(=O)C2)C)O[C@@H]4C(=O)O[C@H]3c1cocc1)C)(C)C
InChI InChI=1S/C27H34O9/c1-23(2)16-10-17(29)25(4)15(26(16,13-28)18(35-23)11-19(30)32-5)6-8-24(3)20(14-7-9-33-12-14)34-22(31)21-27(24,25)36-21/h7,9,12,15-16,18,20-21,28H,6,8,10-11,13H2,1-5H3/t15-,16-,18-,20-,21+,24-,25-,26+,27+/m0/s1
InChIKey XCLFXSUTXZKNFU-QGBLDOQRSA-N
Formula C27H34O9
HBA 9
HBD 1
MW 502.56
Rotatable Bonds 4
TPSA 124.8
LogP 2.75
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.74
Exact Mass 502.22
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Vepris uguenensis Rutaceae Plantae 2695421
2 Vepris uguenensis Rutaceae Plantae 2695421
3 Vepris uguenensis Rutaceae Plantae 2695421

Showing of synonyms

  • Cheplogoi PK, Mulholland DA, et al. (2008). An azole, an amide and a limonoid from Vepris uguenensis (Rutaceae). Phytochemistry,2008,69(6),1384-1388. [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: 24862590
Nmrshiftdb2: 60072532

No compound-protein relationship available.

Structure

SMILES: c1occc1C(OC(=O)C(C234)O4)C3CCC5C6C(COC6)CC(=O)C25

Level: 1

Mol. Weight: 502.56 g/mol

Structure

SMILES: C123C(O3)C(=O)OCC2CCC4C5C(COC5)CC(=O)C14

Level: 0

Mol. Weight: 502.56 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 502.56 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-5.19
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.820
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.450
Plasma Protein Binding
50.74
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
11.110
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.200
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.150
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.450
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
-708.910
Rat (Acute)
5.880
Rat (Chronic Oral)
2.160
Fathead Minnow
3.470
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
490.810
Hydration Free Energy
-2.850
Log(D) at pH=7.4
2.050
Log(P)
2.42
Log S
-4.42
Log(Vapor Pressure)
-9.48
Melting Point
216.64
pKa Acid
4.57
pKa Basic
3.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7791
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7791
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7745
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7745
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7740
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7740
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7665
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7665
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7606
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7606
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7488
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7488
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7448
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7448
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.7438
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.7438
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7408
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7408
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7382
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7382
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7358
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7358
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7305
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7305
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7300
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7300
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 2 0.7273
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7273
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 2 0.7273
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7273
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7270
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7270
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7212
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7212
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7184
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7184
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7177
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7177
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7172
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7172
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7171
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7171
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7157
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7157
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7143
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7143
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7142
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7142
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 2 0.7138
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 2 0.7138
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7113
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7113
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7091
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7091
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 2 0.7074
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 2 0.7074
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7071
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7071
Alanine racemase Q180W0 Q180W0_CLOD6 Clostridioides difficile 2 0.7067
Alanine racemase Q180W0 Q180W0_CLOD6 Clostridioides difficile 2 0.7067
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7053
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7053
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7041
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7041
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7008
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7008
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7001
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7001

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