Khayanone-1,6-dibenzoate - Compound Card

Khayanone-1,6-dibenzoate

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Khayanone-1,6-dibenzoate

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles COC(=O)[C@H]([C@H]1C(C)(C)C(=O)[C@H]2C(=O)[C@]1(C)[C@H]1CC[C@@]3([C@H]([C@]1(C2)OC(=O)c1ccccc1)CC(=O)O[C@H]3c1ccoc1)C)OC(=O)c1ccccc1
InChI InChI=1S/C41H42O11/c1-38(2)31(30(37(47)48-5)51-35(45)23-12-8-6-9-13-23)40(4)27-16-18-39(3)28(20-29(42)50-34(39)25-17-19-49-22-25)41(27,21-26(32(38)43)33(40)44)52-36(46)24-14-10-7-11-15-24/h6-15,17,19,22,26-28,30-31,34H,16,18,20-21H2,1-5H3/t26-,27+,28+,30-,31-,34-,39+,40+,41+/m0/s1
InChIKey ODVSJFWWHXUHJP-HYALVKKASA-N
Formula C41H42O11
HBA 11
HBD 0
MW 710.78
Rotatable Bonds 7
TPSA 152.48
LogP 6.11
Number Rings 7
Number Aromatic Rings 3
Heavy Atom Count 52
Formal Charge 0
Fraction CSP3 0.46
Exact Mass 710.27
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: 163040319
Nmrshiftdb2: 60045079

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OCC2CC(=O)C(C3)C(=O)C2C(C34OC(=O)c5ccccc5)CCC6C4CC(=O)OC6c7ccoc7

Level: 3

Mol. Weight: 710.78 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CC(=O)C(C3)C(=O)C2C(CCC4C5CC(=O)OC4)C35OC(=O)c6ccccc6

Level: 2

Mol. Weight: 710.78 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CC(=O)C(C3=O)CC(C4C23)C5C(CC4)C(OC(=O)C5)c6ccoc6

Level: 2

Mol. Weight: 710.78 g/mol

Structure

SMILES: c1ccccc1C(=O)OC23C(C4C(=O)C(C3)C(=O)CC4)CCC5C2CC(=O)OC5c6ccoc6

Level: 2

Mol. Weight: 710.78 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC(CC2=O)C(C(=O)C23)C4C(C3)C5C(CC4)COC(=O)C5

Level: 1

Mol. Weight: 710.78 g/mol

Structure

SMILES: c1ccccc1C(=O)OC23C(C4C(=O)C(C3)C(=O)CC4)CCC5C2CC(=O)OC5

Level: 1

Mol. Weight: 710.78 g/mol

Structure

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

Level: 1

Mol. Weight: 710.78 g/mol

Structure

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

Level: 0

Mol. Weight: 710.78 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 710.78 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 710.78 g/mol

Antifeedant
Antiviral

Absorption

Caco-2 (logPapp)
-5.08
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
3.660
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1150.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.790
Plasma Protein Binding
97.77
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
9.960
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-29.590
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.020
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.670
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
-2092800.110
Rat (Acute)
4.580
Rat (Chronic Oral)
2.870
Fathead Minnow
2648.310
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
230850.850
Hydration Free Energy
-2.920
Log(D) at pH=7.4
5.000
Log(P)
5.33
Log S
-5.98
Log(Vapor Pressure)
-7564.69
Melting Point
261.67
pKa Acid
-25.15
pKa Basic
0.89
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9376
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9376
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9338
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9338
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9083
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9083
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9011
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9011
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8955
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8955
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8901
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8901
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8897
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8897
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8880
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8880
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8860
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8860
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8749
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8749
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 3 0.8645
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 3 0.8645
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 3 0.8585
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 3 0.8585
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8507
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8507
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8388
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8388
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8364
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8364
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7830
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7830
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7820
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7820
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7784
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7784
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7783
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7783
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7774
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7774
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7759
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7759
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7680
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7680
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7666
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7666
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7660
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7660
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7653
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7653
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7651
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7651
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7609
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7609
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7561
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7561
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7522
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7522
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7504
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7504
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 3 0.7477
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7477
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 3 0.7477
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7477
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7473
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7473
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 3 0.7439
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 3 0.7439
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7406
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7406
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7404
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7404
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.7401
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.7401
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7370
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7370
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7348
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7348
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 3 0.7323
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 3 0.7323
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7277
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7277
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7276
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7276
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7235
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7235
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7171
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7171
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7161
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7161
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7157
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7157
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 2 0.7156
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 2 0.7156
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7154
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7154
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7139
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7139
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7133
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7133
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7130
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7130
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7121
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7121
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7118
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7118
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7093
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7093
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7090
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7090
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7088
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7088
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7086
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7086
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7071
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7071
Thymidylate synthase P45352 TYSY_RAT Rattus norvegicus 2 0.7058
Thymidylate synthase P45352 TYSY_RAT Rattus norvegicus 2 0.7058
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 3 0.7056
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 3 0.7056
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7035
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7035
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7019
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7019
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7017
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7017
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7005
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7005

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