N-methoxy-5-oxoaporphinoid - Compound Card

N-methoxy-5-oxoaporphinoid

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N-methoxy-5-oxoaporphinoid

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Aporphine Alkaloid
Canonical Smiles COC1C(=O)Cc2c3C1Cc1ccccc1c3c1c(c2)OCO1
InChI InChI=1S/C19H16O4/c1-21-18-13-6-10-4-2-3-5-12(10)17-16(13)11(7-14(18)20)8-15-19(17)23-9-22-15/h2-5,8,13,18H,6-7,9H2,1H3
InChIKey RINICNGNKUISSB-UHFFFAOYSA-N
Formula C19H16O4
HBA 4
HBD 0
MW 308.33
Rotatable Bonds 1
TPSA 44.76
LogP 2.86
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 308.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artabotrys monteiroae Annonaceae Plantae 1636225

Showing of synonyms

  • Nyandoro SS, Joseph CC, et al. (2013). New antimicrobial, mosquito larvicidal and other metabolites from two Artabotrys species. Natural Product Research,2013,27(16),1450-458. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)cc3c4c2c5c(cccc5)CC4CC(=O)C3

Level: 0

Mol. Weight: 308.33 g/mol

Mosquito larvicidal potency

Absorption

Caco-2 (logPapp)
-5.12
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.430
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.22

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.420
Plasma Protein Binding
59.35
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.100
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.780
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.570
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.730
Micronucleos
Safe
NR-AhR
Toxic
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
Toxic
T. Pyriformis
2.460
Rat (Acute)
2.120
Rat (Chronic Oral)
2.000
Fathead Minnow
5.070
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
436.950
Hydration Free Energy
-7.720
Log(D) at pH=7.4
1.870
Log(P)
3.05
Log S
-3.99
Log(Vapor Pressure)
-7.64
Melting Point
139.78
pKa Acid
8.37
pKa Basic
3.71
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9444
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9444
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9390
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9390
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9131
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9131
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9101
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9101
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.9079
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.9079
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9063
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9063
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.9029
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.9029
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.9007
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.9007
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8993
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8993
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8832
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8832
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8774
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8774
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8741
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8741
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8687
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8687
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.8654
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.8654
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8577
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8577
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8530
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8530
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8493
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8493
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8416
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8416
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8363
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8363
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.8307
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.8307
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8218
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8218
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8109
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8109
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8022
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8022
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8020
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8020
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7940
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7940
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7902
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7902
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7788
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7788
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7788
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7788
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7750
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7750
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7735
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7735
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7732
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7732
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7674
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7674
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7670
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7670
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7648
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7648
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7622
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7622
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7604
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7604
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7604
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7604
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7602
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7602
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7601
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7601
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7553
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7553
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7545
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7545
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7543
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7543
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7530
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7530
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7496
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7496
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7494
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7494
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7480
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7480
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7470
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7470
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7468
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7468
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7466
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7466
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7462
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7462
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7457
Calmodulin-2 P0DP24 CALM2_HUMAN Homo sapiens 3 0.7457
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7457
Calmodulin-2 P0DP24 CALM2_HUMAN Homo sapiens 3 0.7457
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7450
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7450
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7449
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7449
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7448
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7448
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7440
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7440
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7434
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7434
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7430
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7430
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7415
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7415
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7366
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7366
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7361
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7361
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7338
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7338
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7336
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7336
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7306
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7306
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7268
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7268
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 2 0.7230
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 2 0.7230
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7205
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7205
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7190
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7190
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7181
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7181
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7174
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7174
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7172
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7172
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7170
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7170
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7156
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7156
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7131
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7131
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7118
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7118
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7114
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7114
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7111
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7111
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7102
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7102
Cholesterol oxidase P22637 CHOD_BREST Brevibacterium sterolicum 3 0.7102
Cholesterol oxidase P22637 CHOD_BREST Brevibacterium sterolicum 3 0.7102
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7095
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7095
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7072
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7072
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7065
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7065
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7061
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7061
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7057
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7057
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7048
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7048
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7048
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7048
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7043
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7043
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7016
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7016

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