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1,3,5,6-tetrahydroxyxanthone

Family: Plantae - Hypericaceae
Kingdom: Plantae
Class: Xanthone
- Subclass: Tetrahydroxyxanthone

Canonical Smiles	Oc1cc(O)c2c(c1)oc1c(c2=O)ccc(c1O)O
InChI	InChI=1S/C13H8O6/c14-5-3-8(16)10-9(4-5)19-13-6(11(10)17)1-2-7(15)12(13)18/h1-4,14-16,18H
InChIKey	CCEBJWKUMKKCDF-UHFFFAOYSA-N
Formula	C₁₃H₈O₆
HBA	6
HBD	4
MW	260.2
Rotatable Bonds	0
TPSA	111.13
LogP	1.77
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	19
Formal Charge	0
Fraction CSP3	0.0
Exact Mass	260.03
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Garcinia nobilis	Clusiaceae	Plantae	469933
2	Garcinia polyantha	Guttiferae	Plantae	469941
3	Hypericum roeperianum	Guttiferae	Plantae	—
4	Hypericum roeperianum	Hypericaceae	Plantae	—
5	Hypericum roeperianum	Hypericaceae	Plantae	—

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]
Demgne OMF, Damen F, et al. (2021). Botanicals and phytochemicals from the bark of Hypericum roeperianum (Hypericaceae) had strong antibacterial activity and showed synergistic effects with antibiotics against multidrug-resistant bacteria expressing active efflux pumps.. Journal of ethnopharmacology,2021, 277, 114257. [View] [PubMed]
Guefack MF, Damen F, et al. (2020). Cytotoxic Constituents of the Bark of Hypericum roeperianum towards Multidrug-Resistant Cancer Cells.. Evidence-based complementary and alternative medicine : eCAM,2020, 2020, 4314807. [View] [PubMed]
Louh GN, Lannang AM, et al. (2008). Polyanxanthone A, B and C, three xanthones from the wood trunk of Garcinia polyantha Oliv.. Phytochemistry,2008, 69(4), 1013-1017. [View] [PubMed]
Damen F, Simo Mpetga JD, et al. (2022). Roeperone A, a new tetraoxygenated xanthone and other compounds from the leaves of Hypericum roeperianum Schimp. (Hypericaceae).. Natural product research,2022, 36(8), 2071-2077. [View] [PubMed]

Pubchem: 5479774

Cas: 5084-31-1

Zinc: ZINC000014764374

Nmrshiftdb2: 60025834

Chembl: CHEMBL448040

Comptox: DTXSID80420484

Bindingdb: 50292547

CPRiL: 168823

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

Level: 0

Mol. Weight: 260.2 g/mol

Anti-inflammatory

Antibacterial

Absorption

Caco-2 (logPapp): -5.29
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.12
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.03

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.72
Plasma Protein Binding: 73.67
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: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 7.45
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.62
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.13
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.52
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 4.29
Rat (Acute): 2.28
Rat (Chronic Oral): 3.26
Fathead Minnow: 4.02
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 464.33
Hydration Free Energy: -12.83
Log(D) at pH=7.4: 1.87
Log(P): 2.32
Log S: -2.8
Log(Vapor Pressure): -8.14
Melting Point: 312.23
pKa Acid: 5.05
pKa Basic: 7.47

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9353
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9299
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9292
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9241
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9193
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	3	0.9152
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.9143
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8891
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8880
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8814
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8792
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8768
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	4	0.8762
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.8721
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8663
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8630
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8544
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8537
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.8536
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8532
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8530
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.8520
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8436
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8392
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8370
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8360
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8329
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.8328
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8327
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	3	0.8306
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8303
Anthranilate phosphoribosyltransferase	P9WFX5	TRPD_MYCTU	Mycobacterium tuberculosis	3	0.8258
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.8255
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8251
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8245
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8209
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	3	0.8173
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.8162
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8150
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8131
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8128
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8125
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8093
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8073
Cyclin-dependent kinase 6	Q00534	CDK6_HUMAN	Homo sapiens	3	0.8057
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8053
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8034
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8026
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8024
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.7969
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7959
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	3	0.7957
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.7945
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7893
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7847
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	4	0.7846
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	4	0.7808
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7806
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7795
cAMP-dependent protein kinase catalytic subunit alpha	P05132	KAPCA_MOUSE	Mus musculus	3	0.7780
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7776
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7757
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7749
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7730
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7724
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7721
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7719
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.7713
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7693
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7645
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7645
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7635
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7635
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7627
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7622
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7596
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7588
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7582
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7572
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7560
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7558
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7548
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7535
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7519
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7507
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7486
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7466
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	3	0.7466
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7449
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7444
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7439
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7436
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7425
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7425
Protoporphyrinogen oxidase, mitochondrial	O24164	PPOM_TOBAC	Nicotiana tabacum	3	0.7409
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7408
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7397
Protein mono-ADP-ribosyltransferase PARP14	Q460N5	PAR14_HUMAN	Homo sapiens	3	0.7376
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7374
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7371
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7370
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7354
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7342
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7324
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	3	0.7318
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	3	0.7305
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7295
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7285
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7277
Catalase-peroxidase	Q3JNW6	KATG_BURP1	Burkholderia pseudomallei	3	0.7262
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7256
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.7254
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7238
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7219
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	3	0.7206
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7205
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7201
Nitrogen regulatory protein P-II	P70731	P70731_AZOBR	Azospirillum brasilense	3	0.7196
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7168
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7153
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7138
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7131
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7128
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7127
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7120
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7118
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7104
Riboflavin kinase	Q969G6	RIFK_HUMAN	Homo sapiens	4	0.7100
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7097
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7090
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7089
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7086
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7067
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7066
Granule-bound starch synthase 1, chloroplastic/amyloplastic	Q0DEV5	SSG1_ORYSJ	Oryza sativa subsp. japonica	3	0.7066
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7054
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7038
Transthyretin	P02766	TTHY_HUMAN	Homo sapiens	3	0.7036
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7032
Decapping and exoribonuclease protein	O70348	DXO_MOUSE	Mus musculus	3	0.7028
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	4	0.7018
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7009
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7006
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7004
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7001

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