Toddaliopsin B - Compound Card

Toddaliopsin B

Select a section from the left sidebar

Toddaliopsin B

Structure
Zoomed Structure
  • Family: Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Acridone Alkaloid
Canonical Smiles COc1cc2c(c(c1OC)OC)c(=O)c1c(n2COC(=O)C)cccc1
InChI InChI=1S/C19H19NO6/c1-11(21)26-10-20-13-8-6-5-7-12(13)17(22)16-14(20)9-15(23-2)18(24-3)19(16)25-4/h5-9H,10H2,1-4H3
InChIKey YMFPNVLLKUBOIG-UHFFFAOYSA-N
Formula C19H19NO6
HBA 7
HBD 0
MW 357.36
Rotatable Bonds 5
TPSA 75.99
LogP 2.7
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.26
Exact Mass 357.12
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: 11515966
Nmrshiftdb2: 20249211

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)
-4.54
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.380
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.170
Plasma Protein Binding
55.76
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
2.460
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.670
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.560
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.920
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
-0.170
Rat (Acute)
2.240
Rat (Chronic Oral)
2.160
Fathead Minnow
5.270
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
448.530
Hydration Free Energy
-7.910
Log(D) at pH=7.4
1.190
Log(P)
1.59
Log S
-3.66
Log(Vapor Pressure)
-7.09
Melting Point
162.86
pKa Acid
7.42
pKa Basic
2.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9673
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9604
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9363
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9340
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9336
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9248
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9118
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9000
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8938
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8902
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8813
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8810
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8722
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8694
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8670
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8666
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8634
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8611
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8610
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8605
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8547
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8521
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8413
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8380
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8372
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8252
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8201
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8184
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8102
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8088
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8049
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7953
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7898
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7845
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7831
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7829
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7818
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7807
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7749
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7742
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7739
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7715
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7711
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7690
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7672
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7660
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7643
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7637
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7586
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7563
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7513
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7504
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 4 0.7502
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7498
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7495
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7463
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7456
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7452
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7448
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7439
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7437
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7421
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7412
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7409
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7401
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7399
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7397
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7381
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7359
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7358
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7305
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7291
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7290
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7279
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7278
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7275
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7273
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7271
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7262
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7239
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7228
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7217
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7205
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7197
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 2 0.7181
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7174
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7166
Orotidine 5'-phosphate decarboxylase Q5L0U0 PYRF_GEOKA Geobacillus kaustophilus 3 0.7164
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 2 0.7164
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7161
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7159
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7157
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7153
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7144
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7143
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7133
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7113
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7111
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7111
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7101
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7081
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7079
NAD(P)H-dependent FMN reductase LOT6 Q07923 LOT6_YEAST Saccharomyces cerevisiae 5 0.7075
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7066
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7061
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7061
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7060
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7039
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7027
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7023
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7019
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7009

Download SDF