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Toddaliopsin C

Family: Plantae - Rutaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Acridone Alkaloid

Canonical Smiles	COc1cc2c(c(c1OC)O)c(=O)c1c(n2COC(=O)C)cccc1
InChI	InChI=1S/C18H17NO6/c1-10(20)25-9-19-12-7-5-4-6-11(12)16(21)15-13(19)8-14(23-2)18(24-3)17(15)22/h4-8,22H,9H2,1-3H3
InChIKey	MXIJLTRSYDOKCJ-UHFFFAOYSA-N
Formula	C₁₈H₁₇NO₆
HBA	7
HBD	1
MW	343.34
Rotatable Bonds	4
TPSA	86.99
LogP	2.4
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.22
Exact Mass	343.11
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: 11530261

Zinc: ZINC000014774883

Nmrshiftdb2: 60063113

No compound-protein relationship available.

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

Level: 0

Mol. Weight: 343.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.54
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.500
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.72

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.290
Plasma Protein Binding: 54.52
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: 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: 2.840
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.360
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.650
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.290
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 1.600
Rat (Acute): 2.110
Rat (Chronic Oral): 2.360
Fathead Minnow: 4.980
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 442.440
Hydration Free Energy: -9.360
Log(D) at pH=7.4: 1.530
Log(P): 1.85
Log S: -4.04
Log(Vapor Pressure): -7.51
Melting Point: 171.14
pKa Acid: 5.97
pKa Basic: 3.97

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	0.9543
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9448
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9321
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9227
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9189
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9139
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8956
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8897
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.8878
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8876
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	3	0.8792
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8660
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8640
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8625
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.8609
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8443
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8434
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8393
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8375
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.8342
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8331
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	3	0.8304
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	4	0.8295
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8295
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.8294
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8284
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.8246
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.8219
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8120
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8115
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8040
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8025
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	3	0.7944
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7938
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7923
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7773
NmrA-like family domain-containing protein 1	Q9HBL8	NMRL1_HUMAN	Homo sapiens	3	0.7769
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7760
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.7739
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	2	0.7729
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7726
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7692
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7689
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7653
Glutathione S-transferase A1	P08263	GSTA1_HUMAN	Homo sapiens	3	0.7640
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7632
cGMP-dependent protein kinase, putative	A5K0N4	A5K0N4_PLAVS	Plasmodium vivax	3	0.7592
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7576
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7551
Glutamate receptor ionotropic, kainate 1	P22756	GRIK1_RAT	Rattus norvegicus	3	0.7548
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7540
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7525
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7489
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q08210	PYRD_PLAF7	Plasmodium falciparum	3	0.7473
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7425
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7410
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7385
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7385
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7366
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7364
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7361
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7358
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7337
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7308
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7296
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	3	0.7267
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7264
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7212
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7212
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7204
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7196
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7194
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7188
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7186
Orotidine 5'-phosphate decarboxylase	Q5L0U0	PYRF_GEOKA	Geobacillus kaustophilus	3	0.7177
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7177
Metallo-beta-lactamase type 2	P26918	BLAB_AERHY	Aeromonas hydrophila	3	0.7170
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7167
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7163
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7126
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.7119
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7109
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.7105
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7102
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7069
L-seryl-tRNA(Sec) kinase	Q58933	PSTK_METJA	Methanocaldococcus jannaschii	2	0.7065
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7064
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7054
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	2	0.7054
Aklavinone 12-hydroxylase RdmE	Q54530	DNRF_STREF	Streptomyces purpurascens	4	0.7053
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7052
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7049
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1	Q9Y3Z3	SAMH1_HUMAN	Homo sapiens	3	0.7044
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7041
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7036
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7027
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	3	0.7017
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7014
Egl nine homolog 1	Q9GZT9	EGLN1_HUMAN	Homo sapiens	3	0.7012
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	2	0.7012
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7007
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7005
NmrA-like family domain-containing protein 1	Q9HBL8	NMRL1_HUMAN	Homo sapiens	3	0.7003

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