Select a section from the left sidebar
Khayanone-(S)-methoxy-alpha-(trifluoromethyl)phenylacetate ester
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Limonoid
Canonical Smiles | COC(=O)[C@H]([C@@H]1[C@]2(C)C(OC(=O)C(C(F)(F)F)(c3ccccc3)OC)[C@H](C(=O)C1(C)C)C[C@]1([C@@H]2CC[C@@]2([C@H]1CC(=O)O[C@H]2c1ccoc1)C)O)O |
---|---|
InChI | InChI=1S/C37H43F3O11/c1-32(2)26(25(42)30(44)47-5)34(4)22-12-14-33(3)23(16-24(41)50-28(33)19-13-15-49-18-19)35(22,46)17-21(27(32)43)29(34)51-31(45)36(48-6,37(38,39)40)20-10-8-7-9-11-20/h7-11,13,15,18,21-23,25-26,28-29,42,46H,12,14,16-17H2,1-6H3/t21-,22+,23+,25-,26-,28-,29?,33+,34+,35+,36?/m0/s1 |
InChIKey | OBQBTYWXXGLSGM-HGPYRURNSA-N |
Formula | C37H43F3O11 |
HBA | 11 |
HBD | 2 |
MW | 720.73 |
Rotatable Bonds | 7 |
TPSA | 158.8 |
LogP | 4.83 |
Number Rings | 6 |
Number Aromatic Rings | 2 |
Heavy Atom Count | 51 |
Formal Charge | 0 |
Fraction CSP3 | 0.62 |
Exact Mass | 720.28 |
Number of Lipinski Rule Violations | 2 |
# | Species | Family | Kingdom | NCBI Taxonomy ID |
---|---|---|---|---|
1 | Khaya senegalensis | Meliaceae | Plantae | 587579 |
Showing of synonyms
Khayanone-(S)-methoxy-alpha-(trifluoromethyl)phenylacetate ester
Pubchem:
162817155
No compound-protein relationship available.
SMILES: c1ccccc1CC(=O)OC2C(CCC(=O)C23)C4C(C3)C5C(CC4)C(OC(=O)C5)c6ccoc6
Level: 2
Mol. Weight: 720.73 g/mol
SMILES: c1ccccc1CC(=O)OC2C(CCC(=O)C23)C4C(C3)C5C(CC4)COC(=O)C5
Level: 1
Mol. Weight: 720.73 g/mol
SMILES: c1occc1C(OC(=O)C2)C3CCC(C4C23)C5CC(C4)C(=O)CC5
Level: 1
Mol. Weight: 720.73 g/mol
SMILES: C12C(=O)CCC(C2)C3C(C1)C4C(CC3)COC(=O)C4
Level: 0
Mol. Weight: 720.73 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 720.73 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 720.73 g/mol
Antifeedant
Antiviral
Absorption
- Caco-2 (logPapp)
- -5.41
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -2.900
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 311.09
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.520
- Plasma Protein Binding
- 89.9
- 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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 9.440
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.400
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.740
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.000
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Toxic
- 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
- -571095.300
- Rat (Acute)
- 3.580
- Rat (Chronic Oral)
- 2.940
- Fathead Minnow
- 731.860
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 60289.760
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 4.720
- Log(P)
- 3.91
- Log S
- -6.9
- Log(Vapor Pressure)
- -1953.4
- Melting Point
- 261.92
- pKa Acid
- 3.19
- pKa Basic
- 2.01
Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
---|---|---|---|---|---|
Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 1.0080 |
Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 1.0080 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8871 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8871 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8843 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8843 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8828 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8828 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8733 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8733 |
Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.8672 |
Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.8672 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8614 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8614 |
Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.8599 |
Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.8599 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8495 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8495 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8420 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8420 |
Antitumor antibiotic C-1027 apoprotein | Q06110 | CAGA_STRGL | Streptomyces globisporus | 3 | 0.8339 |
Antitumor antibiotic C-1027 apoprotein | Q06110 | CAGA_STRGL | Streptomyces globisporus | 3 | 0.8339 |
CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8297 |
CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8297 |
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8215 |
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8215 |
Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.8010 |
Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.8010 |
Stimulator of interferon genes protein | Q86WV6 | STING_HUMAN | Homo sapiens | 3 | 0.7949 |
Stimulator of interferon genes protein | Q86WV6 | STING_HUMAN | Homo sapiens | 3 | 0.7949 |
Insulin-degrading enzyme | P14735 | IDE_HUMAN | Homo sapiens | 2 | 0.7901 |
Insulin-degrading enzyme | P14735 | IDE_HUMAN | Homo sapiens | 2 | 0.7901 |
Nociceptin receptor | P41146 | OPRX_HUMAN | Homo sapiens | 3 | 0.7873 |
Nociceptin receptor | P41146 | OPRX_HUMAN | Homo sapiens | 3 | 0.7873 |
Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7840 |
Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7840 |
Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7818 |
Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7818 |
Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.7815 |
Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.7815 |
Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7813 |
Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7813 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7793 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7793 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7758 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7758 |
Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7732 |
Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7732 |
Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7711 |
Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7711 |
Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7673 |
Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7673 |
3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7665 |
3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7665 |
cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7593 |
cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7593 |
Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7527 |
Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7527 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7521 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7521 |
Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7505 |
Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7505 |
CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7503 |
CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7503 |
Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7467 |
Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7467 |
D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7424 |
D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7424 |
NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 2 | 0.7415 |
NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 2 | 0.7415 |
Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7379 |
Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7379 |
Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7353 |
Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7353 |
Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7341 |
Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7341 |
Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7299 |
Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7299 |
ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 2 | 0.7272 |
ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 2 | 0.7272 |
Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7227 |
Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7227 |
Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7223 |
Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7223 |
Nucleoside diphosphate kinase | Q5UQL3 | NDK_MIMIV | Acanthamoeba polyphaga mimivirus | 2 | 0.7219 |
Nucleoside diphosphate kinase | Q5UQL3 | NDK_MIMIV | Acanthamoeba polyphaga mimivirus | 2 | 0.7219 |
NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7216 |
NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7216 |
cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7211 |
cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7211 |
Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7191 |
Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7191 |
N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7175 |
N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7175 |
Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7163 |
Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7163 |
Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 2 | 0.7156 |
Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 2 | 0.7156 |
Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 2 | 0.7146 |
Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 2 | 0.7146 |
Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7141 |
Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7141 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7112 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7112 |
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7099 |
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7099 |
Acetylcholinesterase | P22303 | ACES_HUMAN | Homo sapiens | 3 | 0.7071 |
Acetylcholinesterase | P22303 | ACES_HUMAN | Homo sapiens | 3 | 0.7071 |
Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 2 | 0.7066 |
Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 2 | 0.7066 |
Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7032 |
Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7032 |
Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 2 | 0.7025 |
Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 2 | 0.7025 |
Prolyl endopeptidase | P23687 | PPCE_PIG | Sus scrofa | 3 | 0.7013 |
Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7013 |
Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7013 |
Prolyl endopeptidase | P23687 | PPCE_PIG | Sus scrofa | 3 | 0.7013 |
Purine nucleoside phosphorylase | P50389 | PNPH_SACS2 | Saccharolobus solfataricus | 3 | 0.7006 |
Purine nucleoside phosphorylase | P50389 | PNPH_SACS2 | Saccharolobus solfataricus | 3 | 0.7006 |