Khayanone-1,6-dimethoxy-alpha-(trifluoromethyl)phenylacetate ester - Compound Card

Khayanone-1,6-dimethoxy-alpha-(trifluoromethyl)phenylacetate ester

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Khayanone-1,6-dimethoxy-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(=O)[C@H](C(=O)C1(C)C)C[C@]1([C@@H]2CC[C@@]2([C@H]1CC(=O)O[C@H]2c1cocc1)C)OC(=O)C(C(F)(F)F)(c1ccccc1)OC)OC(=O)C(C(F)(F)F)(c1ccccc1)OC
InChI InChI=1S/C47H48F6O13/c1-40(2)33(32(37(57)60-5)65-38(58)44(61-6,46(48,49)50)26-14-10-8-11-15-26)42(4)29-18-20-41(3)30(22-31(54)64-36(41)25-19-21-63-24-25)43(29,23-28(34(40)55)35(42)56)66-39(59)45(62-7,47(51,52)53)27-16-12-9-13-17-27/h8-17,19,21,24,28-30,32-33,36H,18,20,22-23H2,1-7H3/t28-,29+,30+,32-,33-,36-,41+,42+,43+,44?,45?/m0/s1
InChIKey QKKCECYTHOKULT-ZRSWYAKASA-N
Formula C47H48F6O13
HBA 13
HBD 0
MW 934.88
Rotatable Bonds 11
TPSA 170.94
LogP 7.7
Number Rings 7
Number Aromatic Rings 3
Heavy Atom Count 66
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 934.3
Number of Lipinski Rule Violations 3
# 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: 162817153
Nmrshiftdb2: 60045084

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CC(=O)OCC2CC(=O)C(C3)C(=O)C2C(C34OC(=O)Cc5ccccc5)CCC6C4CC(=O)OC6c7ccoc7

Level: 3

Mol. Weight: 934.88 g/mol

Structure

SMILES: c1ccccc1CC(=O)OCC2CC(=O)C(C3)C(=O)C2C(CCC4C5CC(=O)OC4)C35OC(=O)Cc6ccccc6

Level: 2

Mol. Weight: 934.88 g/mol

Structure

SMILES: c1ccccc1CC(=O)OCC2CC(=O)C(C3=O)CC(C4C23)C5C(CC4)C(OC(=O)C5)c6ccoc6

Level: 2

Mol. Weight: 934.88 g/mol

Structure

SMILES: c1ccccc1CC(=O)OC23C(C4C(=O)C(C3)C(=O)CC4)CCC5C2CC(=O)OC5c6ccoc6

Level: 2

Mol. Weight: 934.88 g/mol

Structure

SMILES: c1ccccc1CC(=O)OCC2CC(=O)C(C3=O)CC(C4C23)C5C(CC4)COC(=O)C5

Level: 1

Mol. Weight: 934.88 g/mol

Structure

SMILES: c1ccccc1CC(=O)OC23C(C4C(=O)C(C3)C(=O)CC4)CCC5C2CC(=O)OC5

Level: 1

Mol. Weight: 934.88 g/mol

Structure

SMILES: c1occc1C(OC(=O)C2)C(CC3)C2C(C4)C3C(C(=O)C45)CCC5=O

Level: 1

Mol. Weight: 934.88 g/mol

Structure

SMILES: O=C1CCC(C(=O)C12)C3C(C2)C4C(CC3)COC(=O)C4

Level: 0

Mol. Weight: 934.88 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 934.88 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 934.88 g/mol

Antifeedant
Antiviral

Absorption

Caco-2 (logPapp)
-5.13
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
2805.470
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
367354.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.480
Plasma Protein Binding
85.94
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
8.580
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-8547.750
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-4.350
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.050
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
Toxic
T. Pyriformis
-666737321.120
Rat (Acute)
2.620
Rat (Chronic Oral)
4.680
Fathead Minnow
841623.160
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
74985368.390
Hydration Free Energy
-2.920
Log(D) at pH=7.4
-21.410
Log(P)
6.45
Log S
-11.63
Log(Vapor Pressure)
-2469148.49
Melting Point
335.92
pKa Acid
-17922.41
pKa Basic
-113.52
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 3 0.8922
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 3 0.8922
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8653
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8653
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8620
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8620
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8544
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8544
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8490
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8490
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8324
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8324
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8295
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8295
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.8213
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.8213
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7986
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7986
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7933
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7933
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7811
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7811
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7783
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7783
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7694
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7694
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7657
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7657
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7627
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7627
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7618
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7618
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7614
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7614
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7611
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7611
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7558
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7558
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7464
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7464
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7444
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7444
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7434
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7434
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7432
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7432
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7424
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7424
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7381
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7381
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7325
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7325
Cystathionine gamma-synthase P56069 METB_HELPY Helicobacter pylori 3 0.7323
Cystathionine gamma-synthase P56069 METB_HELPY Helicobacter pylori 3 0.7323
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7280
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7280
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 2 0.7262
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 2 0.7262
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7230
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7230
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7211
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7211
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7191
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7191
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7173
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7173
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7148
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7148
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7140
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7140
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7128
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7128
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7123
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7123
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7096
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7096
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7080
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7080
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7073
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7073
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7050
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7050
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7049
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7049
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7023
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7023

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