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Toddaliopsin B

Family: Plantae - 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

Zinc: ZINC000014774893

Nmrshiftdb2: 20249211

No compound-protein relationship available.

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

Level: 0

Mol. Weight: 357.36 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

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