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Wentixanthone A

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Xanthone

Canonical Smiles	OC[C@@H](COC(=O)c1c(C)cc(c2c1oc1cc(O)cc(c1c2=O)O)C(=O)OC)O
InChI	InChI=1S/C20H18O10/c1-8-3-11(19(26)28-2)15-17(25)16-12(24)4-9(22)5-13(16)30-18(15)14(8)20(27)29-7-10(23)6-21/h3-5,10,21-24H,6-7H2,1-2H3/t10-/m0/s1
InChIKey	LQGDSHBIUYDSQX-JTQLQIEISA-N
Formula	C₂₀H₁₈O₁₀
HBA	10
HBD	4
MW	418.35
Rotatable Bonds	5
TPSA	163.73
LogP	0.96
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	30
Formal Charge	0
Fraction CSP3	0.25
Exact Mass	418.09
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aspergillus wentii	Trichocomaceae	Fungi	5066

Showing of synonyms

Form I.C, Bonus M, et al. (2019). Xanthone, benzophenone and bianthrone derivatives from the hypersaline lake-derived fungus Aspergillus wentii. Bioorg Med Chem,2019,27(20),115005. [View] [PubMed]

Pubchem: 146682317

Nmrshiftdb2: 70067122

Chembl: CHEMBL4546924

No compound-protein relationship available.

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

Level: 0

Mol. Weight: 418.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.28
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.86
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.25

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.97
Plasma Protein Binding: 39.41
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: Non-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: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.74
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -0.01
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.69
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.57
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: -16.71
Rat (Acute): 2.0
Rat (Chronic Oral): 3.55
Fathead Minnow: 4.31
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 541.78
Hydration Free Energy: -8.24
Log(D) at pH=7.4: 2.12
Log(P): 2.04
Log S: -3.81
Log(Vapor Pressure): -9.41
Melting Point: 181.5
pKa Acid: 7.69
pKa Basic: 5.48

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9291
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9242
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9150
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.9102
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9003
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8976
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.8922
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.8902
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8853
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.8813
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8753
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	3	0.8726
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8726
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8574
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8468
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.8439
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8408
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8364
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8336
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8244
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8219
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8204
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	4	0.8196
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8150
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8137
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8132
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8124
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8107
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.8073
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.8030
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.8021
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7975
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7920
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7857
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7845
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7829
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7828
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7825
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7810
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7800
Mitogen-activated protein kinase kinase kinase 7	O43318	M3K7_HUMAN	Homo sapiens	4	0.7769
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7745
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7727
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7716
tRNA(Phe) (4-demethylwyosine(37)-C(7)) aminocarboxypropyltransferase	O58523	TYW2_PYRHO	Pyrococcus horikoshii	3	0.7669
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7653
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7607
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7589
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	3	0.7547
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7523
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7518
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7513
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.7504
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7502
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7480
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7466
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7448
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7417
Beta-glucosidase 12	B8AVF0	BGL12_ORYSI	Oryza sativa subsp. indica	3	0.7409
ADP-ribosylation factor 1, putative	C4LXL1	C4LXL1_ENTHI	Entamoeba histolytica	4	0.7391
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7375
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7332
ADP-ribosylation factor 1, putative	C4LXL1	C4LXL1_ENTHI	Entamoeba histolytica	4	0.7312
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	3	0.7306
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7283
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7241
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7237
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7236
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7226
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7215
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7202
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7174
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7173
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7171
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7169
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7141
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7140
Angiotensin-converting enzyme	Q10714	ACE_DROME	Drosophila melanogaster	3	0.7123
Pol polyprotein	P32542	POL_EIAVC	Equine infectious anemia virus	4	0.7121
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7119
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7116
Protein kinase domain-containing protein	C1EBN1	C1EBN1_MICCC	Micromonas commoda	4	0.7115
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7101
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7064
Nitrogen regulatory protein P-II	P70731	P70731_AZOBR	Azospirillum brasilense	3	0.7058
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7053
Cell division cycle 7-related protein kinase	O00311	CDC7_HUMAN	Homo sapiens	4	0.7046
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7038
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7035
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	3	0.7034
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7029
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7018
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7011
LD-carboxypeptidase	A0A6L8PVW7	A0A1Q4LWC0_BACAN	Bacillus anthracis	3	0.7010
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7003

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