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Evoxanthine

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

Canonical Smiles	COc1c2OCOc2cc2c1c(=O)c1c(n2C)cccc1
InChI	InChI=1S/C16H13NO4/c1-17-10-6-4-3-5-9(10)14(18)13-11(17)7-12-15(16(13)19-2)21-8-20-12/h3-7H,8H2,1-2H3
InChIKey	ULBVHYNIDQSMFC-UHFFFAOYSA-N
Formula	C₁₆H₁₃NO₄
HBA	5
HBD	0
MW	283.28
Rotatable Bonds	1
TPSA	49.69
LogP	2.43
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.19
Exact Mass	283.08
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Pleiocarpa pycnantha	Apocynaceae	Plantae	1220085
2	Vepris lecomteana	Rutaceae	Plantae	1321803
3	Vepris lecomteana	Rutaceae	Plantae	1321803
4	Teclea gerrardii	Rutaceae	Plantae	1237830

Showing of synonyms

Kenmogne Kouam AD, Kenmogne SB, et al. (2019). A rotameric tryptamide alkaloid from the roots of Vepris lecomteana (Pierre) Cheek & T. Heller (Rutaceae).. Fitoterapia,2019, 135, 9-14. [View] [PubMed]
Waffo AF, Coombes PH, et al. (2007). Acridone and furoquinoline alkaloids from Teclea gerrardii(Rutaceae: Toddalioideae) of southern Africa. Phytochemistry, 2007, 68(5), 663–667. [View]
Kouam ADK, Bissoue AN, et al. (2017). Antimicrobial Furoquinoline Alkaloids from Vepris lecomteana (Pierre) Cheek & T. Heller (Rutaceae). Molecules. 2017, 23(1), 13. [View] [PubMed]
Ndongo JT, Mbing JN, et al. (2018). Carbazole-, aspidofractinine-, and aspidocarpamine-type alkaloids from Pleiocarpa pycnantha.. Journal of natural products,2018, 81(5), 1193-1202. [View] [PubMed]

Pubchem: 348484

Cas: 477-82-7

Zinc: ZINC000005495493

Nmrshiftdb2: 60070785

Comptox: DTXSID00324839

CPRiL: 428839

SMILES: O1COc(c12)cc3c(c2)c(=O)c4c([nH]3)cccc4

Level: 0

Mol. Weight: 283.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.65
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -3.930
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.15

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.480
Plasma Protein Binding: 76.05
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: 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: 5.570
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.280
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.600
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.920
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 4.330
Rat (Acute): 2.090
Rat (Chronic Oral): 1.610
Fathead Minnow: 5.000
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: 430.810
Hydration Free Energy: -9.780
Log(D) at pH=7.4: 1.110
Log(P): 2.26
Log S: -4.01
Log(Vapor Pressure): -7.42
Melting Point: 189.64
pKa Acid: 5.17
pKa Basic: 3.01

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9769
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9511
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.9287
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.9283
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.9125
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9079
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9071
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9030
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.8986
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.8912
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8905
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8882
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8860
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8738
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.8705
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.8630
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.8627
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8582
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.8513
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8503
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8465
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8424
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8424
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.8315
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8173
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8078
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7984
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.7965
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7958
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7939
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7871
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7846
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	2	0.7844
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7822
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7810
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7794
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7782
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7754
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7743
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7738
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7728
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7622
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7604
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7592
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7581
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7563
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	2	0.7549
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7545
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7512
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7505
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7502
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7498
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7475
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7466
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7461
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7459
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7458
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7452
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7450
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7445
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7438
cGMP-dependent protein kinase, putative	A5K0N4	A5K0N4_PLAVS	Plasmodium vivax	3	0.7415
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7410
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7407
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7374
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7373
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7373
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7356
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7340
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q08210	PYRD_PLAF7	Plasmodium falciparum	3	0.7337
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7329
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7329
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7318
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7316
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7313
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7310
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7307
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7280
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7258
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7255
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7247
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7220
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7215
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7184
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	2	0.7177
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7176
Deoxyribodipyrimidine photo-lyase	Q8PYK9	Q8PYK9_METMA	Methanosarcina mazei	4	0.7173
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	3	0.7168
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.7164
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7146
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7135
Prostaglandin G/H synthase 2	Q05769	PGH2_MOUSE	Mus musculus	3	0.7120
Diamine acetyltransferase 1	P21673	SAT1_HUMAN	Homo sapiens	2	0.7101
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7094
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	3	0.7093
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7061
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7058
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7053
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7042
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7035
(RS)-norcoclaurine 6-O-methyltransferase	Q5C9L7	6OMT_THLFG	Thalictrum flavum subsp. glaucum	3	0.7032
Aldo-keto reductase family 1 member A1	P50578	AK1A1_PIG	Sus scrofa	3	0.7029
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7017
Oxysterols receptor LXR-beta	P55055	NR1H2_HUMAN	Homo sapiens	3	0.7013
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7010
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7004

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