Oxoanolobine - Compound Card

Oxoanolobine

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Oxoanolobine

Structure
Zoomed Structure
  • Family: Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Oxoaporphine Alkaloid
Canonical Smiles Oc1ccc2c(c1)C(=O)c1c3c2c2OCOc2cc3ccn1
InChI InChI=1S/C17H9NO4/c19-9-1-2-10-11(6-9)16(20)15-13-8(3-4-18-15)5-12-17(14(10)13)22-7-21-12/h1-6,19H,7H2
InChIKey ALNCSCLTBCGURW-UHFFFAOYSA-N
Formula C17H9NO4
HBA 5
HBD 1
MW 291.26
Rotatable Bonds 0
TPSA 68.65
LogP 2.88
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.06
Exact Mass 291.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Anonidium mannii Annonaceae Plantae 2109291

Showing of synonyms

  • Ngangoue MO, Ngameni B, et al. (2021). A phenanthridin-6( 5H )-one derivative and a lanostane-type triterpene with antibacterial properties from Anonidium mannii (Oliv). Engl. & Diels (Annonaceae). Natural product research,2021, 35(21), 4041-4050. [View] [PubMed]
Pubchem: 135985965
Nmrshiftdb2: 60063531

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)cc3c4c2c5c(cccc5)C(=O)c4ncc3

Level: 0

Mol. Weight: 275.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.490
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.280
Plasma Protein Binding
83.75
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
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.590
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.110
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.900
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.010
Micronucleos
Toxic
NR-AhR
Toxic
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
Toxic
T. Pyriformis
3.650
Rat (Acute)
2.360
Rat (Chronic Oral)
1.710
Fathead Minnow
4.800
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
468.380
Hydration Free Energy
-10.170
Log(D) at pH=7.4
2.180
Log(P)
2.82
Log S
-5.88
Log(Vapor Pressure)
-10.01
Melting Point
314.0
pKa Acid
8.15
pKa Basic
3.46
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.9566
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9450
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9310
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.9272
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9099
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9028
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9022
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9011
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8885
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8860
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8845
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8799
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8778
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8778
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8762
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8592
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8590
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8588
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8559
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8479
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8409
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8371
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8367
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8332
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8323
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8297
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8294
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8279
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8241
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8209
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8179
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8166
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8157
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8122
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8079
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.8047
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.8044
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7989
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7961
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7939
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7911
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7900
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7884
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7852
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7840
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7826
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7802
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7793
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7751
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7751
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7732
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7721
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7720
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7696
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7686
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7682
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7681
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7634
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7602
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7596
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7587
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7557
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7555
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7552
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7551
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7525
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7519
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7514
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7494
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.7491
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7464
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7438
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7404
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7386
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7383
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7382
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7381
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7380
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7362
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7357
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7350
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7346
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7339
Adenosine monophosphate-protein transferase Q8ZVF7 Q8ZVF7_PYRAE Pyrobaculum aerophilum 3 0.7326
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7294
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7281
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 3 0.7277
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7275
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7270
High affinity nerve growth factor receptor P04629 NTRK1_HUMAN Homo sapiens 3 0.7258
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7257
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7252
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7247
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7236
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7222
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7204
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7204
Bifunctional dihydrofolate reductase-thymidylate synthase A7UD81 A7UD81_PLAFA Plasmodium falciparum 3 0.7191
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7189
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7187
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 4 0.7186
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7184
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7179
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7175
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7167
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7160
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7148
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7147
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7140
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7139
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7127
Mitogen-activated protein kinase kinase kinase 14 Q99558 M3K14_HUMAN Homo sapiens 3 0.7125
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7105
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7086
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7085
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7079
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7074
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7070
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7034
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7034
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7032
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7032
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7030
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7023
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7021
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7017
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7016
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7009

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