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Monathadiepoxide methyl ether

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Cyclohexane Derivative
- Subclass: Oxygenated Cyclohexane Epoxide Derivative

Canonical Smiles	CO[C@H]1[C@H](OC(=O)c2ccccc2)C2OC2C2[C@@]1(COC(=O)c1ccccc1)O2
InChI	InChI=1S/C22H20O7/c1-25-18-16(28-21(24)14-10-6-3-7-11-14)15-17(27-15)19-22(18,29-19)12-26-20(23)13-8-4-2-5-9-13/h2-11,15-19H,12H2,1H3/t15?,16-,17?,18+,19?,22+/m1/s1
InChIKey	KEKCBORMGWEQCM-PZQNWFJNSA-N
Formula	C₂₂H₂₀O₇
HBA	7
HBD	0
MW	396.4
Rotatable Bonds	6
TPSA	86.89
LogP	2.0
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.36
Exact Mass	396.12
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.

SMILES: c1ccccc1C(=O)OCC23C(O3)C4C(O4)C(C2)OC(=O)c5ccccc5

Level: 2

Mol. Weight: 396.4 g/mol

SMILES: c1ccccc1C(=O)OCC23C(O3)C4C(O4)CC2

Level: 1

Mol. Weight: 396.4 g/mol

SMILES: c1ccccc1C(=O)OC(C2O3)CC(O4)C4C23

Level: 1

Mol. Weight: 396.4 g/mol

SMILES: C12C3C(O3)CCC1O2

Level: 0

Mol. Weight: 396.4 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 396.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.9
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.400
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.29

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.730
Plasma Protein Binding: 34.84
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: 12.420
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.770
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: -0.800
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.410
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: -63.900
Rat (Acute): 3.820
Rat (Chronic Oral): 1.850
Fathead Minnow: 4.950
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 422.020
Hydration Free Energy: -3.080
Log(D) at pH=7.4: 3.080
Log(P): 2.89
Log S: -4.24
Log(Vapor Pressure): -7.25
Melting Point: 79.19
pKa Acid: 6.35
pKa Basic: -3.51

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.9548
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.9548
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9510
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9510
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9327
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9327
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9321
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9321
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.9202
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.9202
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9183
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9183
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.9073
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.9073
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.8742
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.8742
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.8731
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.8731
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8351
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8351
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.8301
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.8301
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.8296
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.8296
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8292
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8292
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8078
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8078
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8034
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8034
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	2	0.7926
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	2	0.7926
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7919
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7919
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7917
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7917
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7913
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7913
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7812
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7812
Metallo-beta-lactamase type 2	P52699	BLAB_SERMA	Serratia marcescens	3	0.7755
Metallo-beta-lactamase type 2	P52699	BLAB_SERMA	Serratia marcescens	3	0.7755
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7753
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7753
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7731
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7731
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7729
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.7729
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.7729
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7729
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	3	0.7622
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	3	0.7622
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7611
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7611
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7552
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7552
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7551
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7551
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7469
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7469
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7430
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7430
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7424
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7424
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7383
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7383
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7368
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7368
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7365
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7365
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7361
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7361
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7352
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7352
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7344
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7344
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7336
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7336
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7330
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7330
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	3	0.7313
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	3	0.7313
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7310
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7310
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	2	0.7300
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	2	0.7300
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7285
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7285
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7280
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7280
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7274
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7274
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7254
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7254
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7252
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7252
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7250
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7250
Pyruvate:ferredoxin oxidoreductase	P94692	PFOR_DESAF	Desulfocurvibacter africanus	3	0.7247
Pyruvate:ferredoxin oxidoreductase	P94692	PFOR_DESAF	Desulfocurvibacter africanus	3	0.7247
Pol protein	Q000H7	Q000H7_9HIV1	Human immunodeficiency virus 1	3	0.7236
Pol protein	Q000H7	Q000H7_9HIV1	Human immunodeficiency virus 1	3	0.7236
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7225
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7225
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7217
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7217
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7208
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7208
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7202
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7202
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7198
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7198
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7194
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7194
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	2	0.7188
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	2	0.7188
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7183
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7183
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7163
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7163
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7147
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7147
Fatty acid-binding protein, adipocyte	P15090	FABP4_HUMAN	Homo sapiens	2	0.7143
Fatty acid-binding protein, adipocyte	P15090	FABP4_HUMAN	Homo sapiens	2	0.7143
Ribosomal protein S6 kinase beta-1	P23443	KS6B1_HUMAN	Homo sapiens	2	0.7139
Ribosomal protein S6 kinase beta-1	P23443	KS6B1_HUMAN	Homo sapiens	2	0.7139
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7135
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7135
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7134
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7134
UDP-N-acetylenolpyruvoylglucosamine reductase	P08373	MURB_ECOLI	Escherichia coli	3	0.7123
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7123
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7123
UDP-N-acetylenolpyruvoylglucosamine reductase	P08373	MURB_ECOLI	Escherichia coli	3	0.7123
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7115
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7115
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7114
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7114
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7109
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7109
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7103
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7103
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7084
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7084
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7075
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7075
Polymerase basic protein 2	P31345	PB2_I75A3	Influenza A virus	2	0.7074
Polymerase basic protein 2	P31345	PB2_I75A3	Influenza A virus	2	0.7074
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7069
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7069
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7055
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7055
Carboxypeptidase A1	P00730	CBPA1_BOVIN	Bos taurus	2	0.7053
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7053
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7053
Carboxypeptidase A1	P00730	CBPA1_BOVIN	Bos taurus	2	0.7053
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7042
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7042
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7037
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7037
Cytochrome P450 3A4	P08684	CP3A4_HUMAN	Homo sapiens	3	0.7029
Cytochrome P450 3A4	P08684	CP3A4_HUMAN	Homo sapiens	3	0.7029
Alanine racemase	Q180W0	Q180W0_CLOD6	Clostridioides difficile	2	0.7028
Alanine racemase	Q180W0	Q180W0_CLOD6	Clostridioides difficile	2	0.7028
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7027
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7027
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7022
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7022
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7018
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7018
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	4	0.7004
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	4	0.7004

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