Methyl angolensate - Compound Card

Methyl angolensate

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Methyl angolensate

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles COC(=O)CC1C2(C)C(CC(=O)C1(C)C)OC13C(=C)C2CCC3(C)C(OC(=O)C1)c1cocc1
InChI InChI=1S/C27H34O7/c1-15-17-7-9-25(4)23(16-8-10-32-14-16)33-22(30)13-27(15,25)34-20-12-19(28)24(2,3)18(26(17,20)5)11-21(29)31-6/h8,10,14,17-18,20,23H,1,7,9,11-13H2,2-6H3
InChIKey YNMYHRYTRCKSMI-UHFFFAOYSA-N
Formula C27H34O7
HBA 7
HBD 0
MW 470.56
Rotatable Bonds 3
TPSA 92.04
LogP 4.56
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 470.23
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Khaya senegalensis Meliaceae Plantae 587579
2 Khaya senegalensis Meliaceae Plantae 587579

Showing of synonyms

  • Nakatani M, Abdelgaleil SAM, et al. (2000). Khayanolides A and B, new rearranged phragmalin limonoid antifeedants from Khaya senegalensis. Tetrahedron Letters,2000,41(33),6473-6477. [View]
  • Abdelgaleil SAM, Okamura H, et al. (2001). Khayanolides, rearranged phragmalin limonoid antifeedants from Khaya senegalensis. Tetrahedron,2001,57(1),119-126. [View]
Pubchem: 419676
Nmrshiftdb2: 70019862
CPRiL: 245920
Structure

SMILES: C1CC(=O)CC(O2)C1C(C3=C)CCC(C234)C(OC(=O)C4)c5ccoc5

Level: 1

Mol. Weight: 470.56 g/mol

Structure

SMILES: C1CC(=O)CC(O2)C1C(C3=C)CCC(C234)COC(=O)C4

Level: 0

Mol. Weight: 470.56 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 470.56 g/mol

Antifeedant

Absorption

Caco-2 (logPapp)
-4.92
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.860
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.58

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.230
Plasma Protein Binding
23.79
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.570
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.330
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.560
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.660
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-217.950
Rat (Acute)
4.080
Rat (Chronic Oral)
2.070
Fathead Minnow
5.100
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
458.650
Hydration Free Energy
-2.980
Log(D) at pH=7.4
3.370
Log(P)
3.27
Log S
-5.43
Log(Vapor Pressure)
-8.16
Melting Point
185.46
pKa Acid
7.05
pKa Basic
4.45
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8546
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8546
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8211
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8211
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8128
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8128
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8098
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8098
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7975
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7975
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7814
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7814
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7792
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7792
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7778
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7778
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7750
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7750
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7673
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7673
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7601
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7601
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7565
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7565
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.7551
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.7551
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7536
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7536
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7520
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7520
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7437
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7437
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
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7391
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7391
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7389
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7389
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7386
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7386
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7386
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7386
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 2 0.7367
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7367
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 2 0.7367
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7367
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7365
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7365
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7353
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7353
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7343
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7343
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 2 0.7338
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 2 0.7338
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7311
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7311
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7300
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7300
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7288
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7288
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7272
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7272
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7259
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7259
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7230
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7230
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7227
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7227
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7220
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7220
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7203
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7203
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7195
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7195
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7194
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7194
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7191
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7191
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7189
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7189
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7170
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7170
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7169
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7169
Cholesterol oxidase P22637 CHOD_BREST Brevibacterium sterolicum 3 0.7162
Cholesterol oxidase P22637 CHOD_BREST Brevibacterium sterolicum 3 0.7162
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7159
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7159
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 2 0.7156
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 2 0.7156
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7152
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7152
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7142
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7142
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7105
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7105
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7103
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7103
Alanine racemase Q180W0 Q180W0_CLOD6 Clostridioides difficile 2 0.7101
Alanine racemase Q180W0 Q180W0_CLOD6 Clostridioides difficile 2 0.7101
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7090
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7090
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7086
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7086
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7070
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7070
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7066
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7066
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7060
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7060
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7041
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7041
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7041
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7041
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7039
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7039
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7036
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7036
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7032
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7032
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7030
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7030
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7028
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7028
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7027
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7027
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7023
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7023
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7021
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7021
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7018
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7018
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7007
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7007
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7001
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7001

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