Khayanone-(S)-methoxy-alpha-(trifluoromethyl)phenylacetate ester - Compound Card

Khayanone-(S)-methoxy-alpha-(trifluoromethyl)phenylacetate ester

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Khayanone-(S)-methoxy-alpha-(trifluoromethyl)phenylacetate ester

Structure
Zoomed Structure
  • 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

  • Nakatani M, Abdelgaleil SA, et al. (2001). Antifeedant rings B and D opened limonoids from Khaya senegalensis. Journal of Natural Products,2001,64(10),1261-1265. [View] [PubMed]
Pubchem: 162817155

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CC(=O)OC2C(CCC(=O)C23)C4C(C3)C5C(CC4)C(OC(=O)C5)c6ccoc6

Level: 2

Mol. Weight: 720.73 g/mol

Structure

SMILES: c1ccccc1CC(=O)OC2C(CCC(=O)C23)C4C(C3)C5C(CC4)COC(=O)C5

Level: 1

Mol. Weight: 720.73 g/mol

Structure

SMILES: c1occc1C(OC(=O)C2)C3CCC(C4C23)C5CC(C4)C(=O)CC5

Level: 1

Mol. Weight: 720.73 g/mol

Structure

SMILES: C12C(=O)CCC(C2)C3C(C1)C4C(CC3)COC(=O)C4

Level: 0

Mol. Weight: 720.73 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 720.73 g/mol

Structure

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

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