(+)-pipoxide-2-methyl ether - Compound Card

(+)-pipoxide-2-methyl ether

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(+)-pipoxide-2-methyl ether

Structure
Zoomed Structure
  • Family: Annonaceae
  • Kingdom: Plantae
  • Class: Cyclohexane Derivative
    • Subclass: Oxygenated Cyclohexane Epoxide Derivative
Canonical Smiles CO[C@H]1[C@@H](C=CC2[C@@]1(COC(=O)c1ccccc1)O2)OC(=O)c1ccccc1
InChI InChI=1S/C22H20O6/c1-25-19-17(27-21(24)16-10-6-3-7-11-16)12-13-18-22(19,28-18)14-26-20(23)15-8-4-2-5-9-15/h2-13,17-19H,14H2,1H3/t17-,18?,19+,22-/m1/s1
InChIKey KLNVBHGVSMXWOX-XFCGAFINSA-N
Formula C22H20O6
HBA 6
HBD 0
MW 380.4
Rotatable Bonds 6
TPSA 74.36
LogP 2.79
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.27
Exact Mass 380.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Monanthotaxis buchananii Annonaceae Plantae 1202420

Showing of synonyms

  • Liang G-Y, Gray AI, et al. (1988). Polyoxygenated cyclohexane epoxide derivatives from the stem bark of Monanthotaxis buchananii. Phytochemistry,1988,27(12),3857-3860. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OCC23C(O3)C=CC(C2)OC(=O)c4ccccc4

Level: 2

Mol. Weight: 350.37 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC23C(O3)C=CCC2

Level: 1

Mol. Weight: 230.26 g/mol

Structure

SMILES: C12C(O2)CC(C=C1)OC(=O)c3ccccc3

Level: 1

Mol. Weight: 216.24 g/mol

Structure

SMILES: C12C(O2)CCC=C1

Level: 0

Mol. Weight: 96.13 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.370
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.730
Plasma Protein Binding
47.7
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.750
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.810
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.520
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.300
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-26.340
Rat (Acute)
3.160
Rat (Chronic Oral)
2.090
Fathead Minnow
4.860
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
408.710
Hydration Free Energy
-4.640
Log(D) at pH=7.4
3.690
Log(P)
3.78
Log S
-4.89
Log(Vapor Pressure)
-6.91
Melting Point
70.65
pKa Acid
7.5
pKa Basic
-2.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.9543
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.9543
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.9461
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.9461
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9231
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9231
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9159
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9159
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.9119
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.9119
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8723
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8723
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.8675
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.8675
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8547
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8547
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.8379
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.8379
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 4 0.8239
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 4 0.8239
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8172
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8172
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8163
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8163
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8153
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8153
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.8108
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.8108
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 4 0.8076
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 4 0.8076
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8069
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8069
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8054
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8054
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7984
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7984
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7898
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7898
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7877
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7877
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7874
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7874
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7854
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7854
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7776
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7776
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7775
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7775
Heat shock cognate 71 kDa protein P11142 HSP7C_HUMAN Homo sapiens 3 0.7763
Heat shock cognate 71 kDa protein P11142 HSP7C_HUMAN Homo sapiens 3 0.7763
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7743
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7743
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7733
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7733
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7716
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7716
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7713
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7713
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7672
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7672
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7668
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7668
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7666
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7666
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7657
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7657
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7644
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7644
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7644
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7644
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7621
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7621
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7600
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7600
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7583
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7583
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7581
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7581
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7560
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7560
Bifunctional protein GlmU P43889 GLMU_HAEIN Haemophilus influenzae 3 0.7547
Bifunctional protein GlmU P43889 GLMU_HAEIN Haemophilus influenzae 3 0.7547
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7511
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7511
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7491
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7491
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7490
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7490
Genome polyprotein Q99AU2 Q99AU2_9HEPC Hepatitis C virus subtype 1b 3 0.7438
Genome polyprotein Q99AU2 Q99AU2_9HEPC Hepatitis C virus subtype 1b 3 0.7438
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7437
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7437
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7436
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7436
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7425
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7425
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7374
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7374
Dipeptidyl peptidase 4 P14740 DPP4_RAT Rattus norvegicus 2 0.7372
Dipeptidyl peptidase 4 P14740 DPP4_RAT Rattus norvegicus 2 0.7372
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7371
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7371
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7369
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7369
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7350
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7350
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7348
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7348
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7344
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7344
Cytochrome P450 3A4 P08684 CP3A4_HUMAN Homo sapiens 3 0.7329
Cytochrome P450 3A4 P08684 CP3A4_HUMAN Homo sapiens 3 0.7329
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7319
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7319
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7302
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7302
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7289
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7289
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 2 0.7286
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 2 0.7286
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7256
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7256
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7255
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7255
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7252
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7252
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7227
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7227
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7201
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7201
UDP-N-acetylenolpyruvoylglucosamine reductase P08373 MURB_ECOLI Escherichia coli 3 0.7197
UDP-N-acetylenolpyruvoylglucosamine reductase P08373 MURB_ECOLI Escherichia coli 3 0.7197
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7191
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7191
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7190
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7190
Beta sliding clamp P0A988 DPO3B_ECOLI Escherichia coli 2 0.7188
Beta sliding clamp P0A988 DPO3B_ECOLI Escherichia coli 2 0.7188
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7174
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7174
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7171
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7171
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7170
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7170
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7165
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7165
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7151
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7151
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7123
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7123
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7117
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7117
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7114
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7114
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7101
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.7101
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.7101
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7101
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7094
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7094
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7084
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7084
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7063
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7063
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7054
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7054
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7036
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7036
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7025
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7025
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7016
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7016
Cytochrome P450 3A4 P08684 CP3A4_HUMAN Homo sapiens 3 0.7011
Cytochrome P450 3A4 P08684 CP3A4_HUMAN Homo sapiens 3 0.7011
Lanosterol 14-alpha demethylase CYP51 P10614 CP51_YEAST Saccharomyces cerevisiae 3 0.7008
Lanosterol 14-alpha demethylase CYP51 P10614 CP51_YEAST Saccharomyces cerevisiae 3 0.7008
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7005
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7005

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