Tecleanone - Compound Card

Tecleanone

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Tecleanone

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Acridone Alkaloid
Canonical Smiles COc1cc(OC)cc(c1C(=O)c1ccccc1NC)OC
InChI InChI=1S/C17H19NO4/c1-18-13-8-6-5-7-12(13)17(19)16-14(21-3)9-11(20-2)10-15(16)22-4/h5-10,18H,1-4H3
InChIKey QJOXEVMFTGODDY-UHFFFAOYSA-N
Formula C17H19NO4
HBA 5
HBD 1
MW 301.34
Rotatable Bonds 6
TPSA 56.79
LogP 2.99
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 301.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Teclea gerrardii Rutaceae Plantae 1237830

Showing of synonyms

  • Waffo AF, Coombes PH, et al. (2007). Acridone and furoquinoline alkaloids from Teclea gerrardii(Rutaceae: Toddalioideae) of southern Africa. Phytochemistry, 2007, 68(5), 663–667. [View]
Pubchem: 304461
Nmrshiftdb2: 60064545

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)c2ccccc2

Level: 1

Mol. Weight: 301.34 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 301.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.38
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.620
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.210
Plasma Protein Binding
48.42
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.940
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.630
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.930
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.890
Micronucleos
Toxic
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
Safe
T. Pyriformis
3.630
Rat (Acute)
2.150
Rat (Chronic Oral)
2.040
Fathead Minnow
4.730
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
376.170
Hydration Free Energy
-11.470
Log(D) at pH=7.4
2.290
Log(P)
3.38
Log S
-4.88
Log(Vapor Pressure)
-6.26
Melting Point
94.92
pKa Acid
9.36
pKa Basic
5.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.9662
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9630
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9553
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.9475
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9378
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.9365
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9264
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9169
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9012
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8967
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8948
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8897
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8845
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8571
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8564
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8553
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8478
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8442
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8380
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8351
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8329
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8316
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8300
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8217
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8162
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8161
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8146
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8141
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8113
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8104
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.8068
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8058
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8053
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.8037
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.8021
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7988
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7967
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7964
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7958
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7947
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7941
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7929
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7888
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7835
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7823
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7782
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7772
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7769
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7768
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7760
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7757
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7738
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7727
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7724
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7712
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7711
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7691
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7682
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7681
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 3 0.7674
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7656
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7656
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7650
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7643
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7606
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 3 0.7591
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7581
Dipeptidyl peptidase 4 P22411 DPP4_PIG Sus scrofa 3 0.7580
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7567
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7558
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7523
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7509
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7499
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7495
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7495
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7489
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 3 0.7470
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7460
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7457
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7457
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.7441
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7434
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7430
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7427
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7425
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7405
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7403
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.7398
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7389
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 2 0.7387
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7383
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7375
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7353
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7348
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7346
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7321
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7319
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7315
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.7307
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7305
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7297
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7296
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7292
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7283
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7279
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7255
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7251
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7249
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7241
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7238
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7227
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 3 0.7215
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7190
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7184
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7178
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7178
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7176
GMP reductase Q81JJ9 GUAC_BACAN Bacillus anthracis 2 0.7176
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7174
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7173
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7172
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7172
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7172
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7164
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7160
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7137
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7131
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7130
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7118
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7116
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7112
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7108
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7101
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7092
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7088
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7087
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7079
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7071
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7070
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q8ZMF7 ISPF_SALTY Salmonella typhimurium 3 0.7070
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 4 0.7061
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7060
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7057
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 2 0.7056
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7052
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7050
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7048
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7033
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7030
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7023
Deoxyribodipyrimidine photo-lyase Q8PYK9 Q8PYK9_METMA Methanosarcina mazei 4 0.7020
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7017
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 2 0.7015
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7013
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7011
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7002

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