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Lichexanthone

Family: Plantae - Sapotaceae
Kingdom: Plantae
Class: Xanthone

Canonical Smiles	COc1cc(C)c2c(c1)oc1c(c2=O)c(O)cc(c1)OC
InChI	InChI=1S/C16H14O5/c1-8-4-9(19-2)6-12-14(8)16(18)15-11(17)5-10(20-3)7-13(15)21-12/h4-7,17H,1-3H3
InChIKey	QDLAGTHXVHQKRE-UHFFFAOYSA-N
Formula	C₁₆H₁₄O₅
HBA	5
HBD	1
MW	286.28
Rotatable Bonds	2
TPSA	68.9
LogP	2.98
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.19
Exact Mass	286.08
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Dacryodes edulis	Burseraceae	Plantae	246365
2	Garcinia nobilis	Clusiaceae	Plantae	469933
3	Mallotus oppositifolius	Euphorbiaceae	Plantae	396489
4	Dialium excelsum	Leguminosae/Fabaceae	Plantae	1608024
5	Trichilia rubescens	Meliaceae	Plantae	1672008
6	Trilepisium madagascariense	Moraceae	Plantae	241931
7	Tridesmostemon omphalocarpoides	Sapotaceae	Plantae	2709045

Showing of synonyms

Dzoyem J, Lannang A, et al. (2015). Anti-inflammatory activity of benzophenone and xanthone derivatives isolated from Garcinia (Clusiaceae) species. Phytochemistry Letters, 2015, 14, 153-158. [View]
Tchangoue YAN, Tchamgoue J, et al. (2020). Antibacterial phloroglucinols derivatives from the leaves of Mallotus oppositifolius (Geisler) Müll. Arg. (Euphorbiaceae).. Fitoterapia,2020, 142, 104527. [View] [PubMed]
Awantu A, Lenta B, et al. (2011). Dialiumoside, an Olean-18-ene Triterpenoid from Dialium excelsum. Zeitschrift für Naturforschung B. 2011, 66(6), 624-628. [View]
Dongmo KJJ, Tali MBT, et al. (2023). In vitro antiplasmodial activity and toxicological profile of extracts, fractions and chemical constituents of leaves and stem bark from Dacryodes edulis (Burseraceae).. BMC complementary medicine and therapies,2023, 23(1), 211. [View] [PubMed]
Fru C, Sandjo L, et al. (2013). Omphalocarpoidone, a new lanostane-type furano-spiro-γ-lactone from the wood of Tridesmostemon omphalocarpoides Engl. (Sapotaceae). Phytochemistry Letters, 2013, 6(4), 676-680. [View]
Tsamo AT, Melong R, et al. (2019). Rubescins I and J, further limonoid derivatives from the stem bark of Trichilia rubescens (Meliaceae).. Natural product research,2019, 33(2), 196-203. [View] [PubMed]
Ango YP, Kapche GDWF, et al. (2016). Three New Derivatives and Others Constituents from the Roots and Twigs of Trilepisium madagascariense DC. Helvetica Chimica Acta, 2016, 99:642-649. [View]

Pubchem: 5358904

Cas: 15222-53-4

Gnps: CCMSLIB00004751507

Chebi: 67821

Nmrshiftdb2: 60029367

Metabolights: MTBLC67821

Chembl: CHEMBL470650

Comptox: DTXSID80164977

CPRiL: 119777

SMILES: c1cccc(c12)oc3c(c2=O)cccc3

Level: 0

Mol. Weight: 286.28 g/mol

Anti-inflammatory

Anti-plasmodial

Absorption

Caco-2 (logPapp): -4.58
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.340
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.86

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.410
Plasma Protein Binding: 72.21
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: 1.660
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.500
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.470
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.890
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: 4.510
Rat (Acute): 2.030
Rat (Chronic Oral): 2.310
Fathead Minnow: 4.970
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 416.510
Hydration Free Energy: -10.510
Log(D) at pH=7.4: 3.080
Log(P): 3.94
Log S: -5.09
Log(Vapor Pressure): -6.93
Melting Point: 215.35
pKa Acid: 7.9
pKa Basic: 3.55

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9470
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.9393
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9385
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9359
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.9340
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.9318
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.9317
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9219
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.9027
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8977
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.8960
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8881
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8790
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8778
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	4	0.8742
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8736
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8732
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8685
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8668
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8652
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8617
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8584
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.8562
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.8551
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.8532
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8526
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8507
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8495
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8446
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8442
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8361
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8359
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8337
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8297
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8295
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.8283
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8256
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8238
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8221
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8203
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8176
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8145
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.8130
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8116
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8102
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.8064
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.8064
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8042
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8040
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.8014
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7988
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7924
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	3	0.7914
Oxygen-insensitive NAD(P)H nitroreductase	P38489	NFSB_ECOLI	Escherichia coli	3	0.7904
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7883
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7882
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7879
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7877
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7866
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7861
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7856
Catalase-peroxidase	Q3JNW6	KATG_BURP1	Burkholderia pseudomallei	3	0.7825
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7746
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7739
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7729
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7722
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7714
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7676
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7646
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7645
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7643
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7630
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7611
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7583
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7557
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7556
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7548
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7532
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7530
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7527
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7521
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7497
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7495
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7485
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7485
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7475
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7434
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	3	0.7421
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7419
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7401
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7400
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7394
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7383
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7376
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7371
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7370
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	3	0.7368
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7353
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial	P08559	ODPA_HUMAN	Homo sapiens	3	0.7349
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7338
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7325
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7317
Dihydrofolate reductase	O30463	O30463_MYCAV	Mycobacterium avium	3	0.7286
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.7280
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7279
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7278
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7271
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7268
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	2	0.7262
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7238
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7235
Orotidine 5'-phosphate decarboxylase	O58462	PYRF_PYRHO	Pyrococcus horikoshii	3	0.7227
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7220
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7204
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7202
Biphenyl dioxygenase subunit alpha	P37333	BPHA_PARXL	Paraburkholderia xenovorans	3	0.7197
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7183
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7183
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7172
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.7159
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7158
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7151
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7137
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7135
Dihydrofolate reductase	P16184	DYR_PNECA	Pneumocystis carinii	3	0.7132
Actin-related protein 3	P61157	ARP3_BOVIN	Bos taurus	3	0.7131
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7127
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7073
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7069
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	4	0.7057
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7055
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7051
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.7046
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7045
DNA mismatch repair protein MutS	P23909	MUTS_ECOLI	Escherichia coli	3	0.7042
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7039
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7038
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7037
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7035
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7022
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7014
tRNA (adenine(9)-N1)-methyltransferase	Q4J894	TRM10_SULAC	Sulfolobus acidocaldarius	4	0.7009
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7002

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