Toddaliopsin A - Compound Card

Toddaliopsin A

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Toddaliopsin A

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Acridone Alkaloid
Canonical Smiles COc1cc2[nH]c3ccccc3c(=O)c2c(c1OC)OC
InChI InChI=1S/C16H15NO4/c1-19-12-8-11-13(16(21-3)15(12)20-2)14(18)9-6-4-5-7-10(9)17-11/h4-8H,1-3H3,(H,17,18)
InChIKey ZUOLILKPUZXGOU-UHFFFAOYSA-N
Formula C16H15NO4
HBA 4
HBD 1
MW 285.3
Rotatable Bonds 3
TPSA 60.55
LogP 2.71
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 285.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Toddaliopsis bremekampii Rutaceae Plantae 992798

Showing of synonyms

  • Naidoo D, Coombes PH, et al. (2005). N-Substituted acridone alkaloids from Toddaliopsis bremekampii (Rutaceae: Toddalioideae) of south-central Africa. Phytochemistry, 2005, 66(14), 1724–1728. [View]
Pubchem: 11716159
Nmrshiftdb2: 70061637

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)[nH]c3c(c2=O)cccc3

Level: 0

Mol. Weight: 285.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.270
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.210
Plasma Protein Binding
59.42
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
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
6.760
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.770
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.080
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.910
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
3.600
Rat (Acute)
2.010
Rat (Chronic Oral)
1.960
Fathead Minnow
4.760
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
413.780
Hydration Free Energy
-11.710
Log(D) at pH=7.4
0.830
Log(P)
2.1
Log S
-3.95
Log(Vapor Pressure)
-6.61
Melting Point
212.34
pKa Acid
5.75
pKa Basic
6.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9648
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9605
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9539
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9326
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9324
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9280
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9242
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9229
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9204
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9158
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9016
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8900
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8865
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8846
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8835
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8814
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8743
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8734
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8715
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8712
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8684
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8659
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8625
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8592
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8580
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8569
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8556
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8498
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8469
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8451
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8443
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8398
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8394
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8365
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8345
Renin P00797 RENI_HUMAN Homo sapiens 3 0.8272
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8152
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8127
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8092
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8078
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8010
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8010
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8006
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8002
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7961
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7945
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7931
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7910
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7895
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7889
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7874
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7847
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7834
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7800
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7789
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7776
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7766
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7762
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7754
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7715
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7713
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7694
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7647
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7626
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7618
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7604
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7604
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7591
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7560
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7560
Cytochrome P450 2C5 P00179 CP2C5_RABIT Oryctolagus cuniculus 3 0.7531
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7530
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7525
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7500
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7497
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7489
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7481
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7461
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7451
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7451
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7447
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7447
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7437
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7427
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7427
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7424
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7417
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7414
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7398
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7392
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7371
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7367
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7364
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7358
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7356
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7354
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7352
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7351
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7344
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7343
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7343
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7332
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7330
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7329
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7302
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7291
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7275
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7274
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7267
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7256
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7251
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7249
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7248
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7239
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7239
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 2 0.7234
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7217
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7197
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7196
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7195
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7189
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7177
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7176
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 2 0.7156
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7155
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7151
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7146
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7128
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7128
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7121
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7117
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7109
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7106
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7093
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 3 0.7092
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7088
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7068
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7051
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 3 0.7026

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