Toddaliopsin D - Compound Card

Toddaliopsin D

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Toddaliopsin D

Structure
Zoomed Structure
  • Family: Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Acridone Alkaloid
Canonical Smiles COCn1c2cc(OC)c(c(c2c(=O)c2c1cccc2)OC)OC
InChI InChI=1S/C18H19NO5/c1-21-10-19-12-8-6-5-7-11(12)16(20)15-13(19)9-14(22-2)17(23-3)18(15)24-4/h5-9H,10H2,1-4H3
InChIKey RVFSXHMVSWIGES-UHFFFAOYSA-N
Formula C18H19NO5
HBA 6
HBD 0
MW 329.35
Rotatable Bonds 5
TPSA 58.92
LogP 2.78
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.28
Exact Mass 329.13
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: 11624058
Nmrshiftdb2: 20249262

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 195.22 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.52
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.190
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.290
Plasma Protein Binding
56.57
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-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
3.590
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
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.500
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.310
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
2.040
Rat (Acute)
2.350
Rat (Chronic Oral)
2.210
Fathead Minnow
5.170
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
430.250
Hydration Free Energy
-9.650
Log(D) at pH=7.4
1.060
Log(P)
1.88
Log S
-2.99
Log(Vapor Pressure)
-6.62
Melting Point
155.13
pKa Acid
7.3
pKa Basic
3.26
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 0.9657
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9629
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9564
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9453
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9400
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9375
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9279
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9161
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9094
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9009
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9002
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8909
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8879
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8877
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8810
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8757
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8750
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8739
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8723
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8642
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8635
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8585
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8467
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8466
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8411
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8407
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8334
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8126
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8106
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8092
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8046
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7973
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7909
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7832
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7831
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7824
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7819
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7811
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7805
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7794
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7789
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7788
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7782
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7760
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7759
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7754
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7746
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7730
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7712
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7673
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7656
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7653
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7643
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7639
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7631
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7629
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7615
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7608
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7602
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7588
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7587
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7587
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7565
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7556
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7555
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7555
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7534
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7529
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7519
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7515
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7492
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7482
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7463
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7452
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7449
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7447
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7442
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7440
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7435
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7420
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7420
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7417
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7412
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7397
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7397
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7390
NAD(P)H-dependent FMN reductase LOT6 Q07923 LOT6_YEAST Saccharomyces cerevisiae 5 0.7382
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7380
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7376
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7373
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7360
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7355
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7345
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7337
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 2 0.7331
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7329
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 2 0.7325
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7317
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7312
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7308
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7302
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7302
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7301
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7299
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7294
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7293
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7291
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 2 0.7275
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 2 0.7275
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 4 0.7266
Phospholipase A2, membrane associated P14555 PA2GA_HUMAN Homo sapiens 2 0.7261
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7254
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7253
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7246
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7238
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7236
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7224
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7218
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7216
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7194
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7190
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7180
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7170
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7166
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 2 0.7165
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7164
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 3 0.7149
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7146
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7137
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7129
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7129
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 2 0.7121
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7117
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7111
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7087
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7080
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7062
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7040
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7029
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7024
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7019
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7011

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