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1,3,6,7-tetrahydroxyxanthone

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

Canonical Smiles	Oc1cc(O)c2c(c1)oc1c(c2=O)cc(c(c1)O)O
InChI	InChI=1S/C13H8O6/c14-5-1-9(17)12-11(2-5)19-10-4-8(16)7(15)3-6(10)13(12)18/h1-4,14-17H
InChIKey	ZHTQCPCDXKMMLU-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

Damen F, Demgne OMF, et al. (2021). A new polyketide from the bark of Hypericum roeperianum Schimp. (Hypericaceae).. Natural product research,2021, 35(14), 2381-2387. [View] [PubMed]
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]

Pubchem: 5281656

Cas: 3542-72-1

Zinc: ZINC000006090922

Kegg Ligand: C10086

Chebi: 7622

Nmrshiftdb2: 60022642

Metabolights: MTBLC7622

Chembl: CHEMBL187265

Comptox: DTXSID30188901

Pdb Ligand: NRA

Bindingdb: 50155447

CPRiL: 151788

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

Level: 0

Mol. Weight: 260.2 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp): -5.32
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.11
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.18

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.69
Plasma Protein Binding: 72.43
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-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: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 7.28
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: Toxic
Maximum Tolerated Dose: 0.99
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.37
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: 4.28
Rat (Acute): 2.17
Rat (Chronic Oral): 3.22
Fathead Minnow: 4.03
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 469.07
Hydration Free Energy: -13.17
Log(D) at pH=7.4: 2.0
Log(P): 2.35
Log S: -2.91
Log(Vapor Pressure): -8.29
Melting Point: 334.17
pKa Acid: 6.01
pKa Basic: 7.43

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	0.9336
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9301
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9294
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9238
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	3	0.9189
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9070
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.9055
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8899
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	3	0.8836
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8802
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8744
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.8724
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.8676
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8663
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8580
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8576
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8540
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8527
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8498
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8483
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.8446
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8412
Nucleoside permease	Q9KPL5	Q9KPL5_VIBCH	Vibrio cholerae serotype O1	4	0.8401
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8397
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.8378
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.8363
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.8357
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8350
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8339
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8331
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8309
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8304
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8298
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.8296
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.8265
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8227
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8221
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8215
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8179
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.8170
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8160
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8153
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8136
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8133
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8083
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8080
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8077
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8070
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.8069
Anthranilate phosphoribosyltransferase	P9WFX5	TRPD_MYCTU	Mycobacterium tuberculosis	3	0.8068
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.8061
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8051
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8039
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8001
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7968
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7958
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7930
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7924
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7910
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7759
Oxygen-insensitive NAD(P)H nitroreductase	P38489	NFSB_ECOLI	Escherichia coli	3	0.7749
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7742
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	4	0.7738
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7734
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7732
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7718
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	3	0.7668
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	3	0.7667
3',5'-cyclic-AMP phosphodiesterase 4A	P27815	PDE4A_HUMAN	Homo sapiens	4	0.7665
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7665
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7638
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7634
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7630
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7622
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7596
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7595
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.7584
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7581
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7575
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7546
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7529
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7506
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7491
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7481
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	3	0.7470
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7457
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7447
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7444
Putative cytochrome P450	Q70AS3	Q70AS3_STRPE	Streptomyces peucetius	4	0.7436
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7421
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7417
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7411
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7399
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7396
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7395
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7393
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7382
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7370
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7328
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7327
Decapping and exoribonuclease protein	O70348	DXO_MOUSE	Mus musculus	3	0.7324
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7318
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7285
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7275
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7272
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7268
Dihydrofolate reductase type 1 from Tn4003	P13955	DYRA_STAAU	Staphylococcus aureus	3	0.7267
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7253
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	3	0.7252
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7242
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7239
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7221
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7220
NAD(P)H dehydrogenase (quinone)	Q9I509	NQOR_PSEAE	Pseudomonas aeruginosa	5	0.7216
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7204
A disintegrin and metalloproteinase with thrombospondin motifs 5	Q9UNA0	ATS5_HUMAN	Homo sapiens	3	0.7185
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7181
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7172
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7171
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7170
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7170
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7169
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7162
Nitrogen regulatory protein P-II	P70731	P70731_AZOBR	Azospirillum brasilense	3	0.7161
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7157
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7154
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7123
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7123
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7109
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7088
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7085
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7075
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7068
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7059
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.7057
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7056
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7055
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7053
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7042
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7039
IAG-nucleoside hydrolase	Q9GPQ4	Q9GPQ4_TRYVI	Trypanosoma vivax	4	0.7036
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7032
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7025
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7023
Cytochrome P450	I6YD01	I6YD01_MYCTU	Mycobacterium tuberculosis	4	0.7008
Ras-related protein Rap-1b	P61224	RAP1B_HUMAN	Homo sapiens	4	0.7004

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