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1,3,5,7-tetrahydroxyxanthone

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

Canonical Smiles	c1(=O)c2c(cc(cc2oc2c(cc(cc12)O)O)O)O
InChI	InChI=1S/C13H8O6/c14-5-1-7-12(18)11-8(16)2-6(15)4-10(11)19-13(7)9(17)3-5/h1-4,14-17H
InChIKey	ZLPUZNUPRZMFJJ-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	Hypericum roeperianum	Hypericaceae	Plantae	—
2	Hypericum roeperianum	Hypericaceae	Plantae	—
3	Psorospermum densipunctatum	Hypericaceae	Plantae	999533

Showing of synonyms

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]
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]
Sass G, Tsamo AT, et al. (2019). Vismione B Interferes with Trypanosoma cruzi Infection of Vero Cells and Human Stem Cell-Derived Cardiomyocytes.. The American journal of tropical medicine and hygiene,2019, 101(6), 1359-1368. [View] [PubMed]

Pubchem: 71473686

Zinc: ZINC000014764400

No compound-protein relationship available.

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

Level: 0

Mol. Weight: 260.2 g/mol

Antibacterial

Absorption

Caco-2 (logPapp): -5.27
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: -0.04

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.67
Plasma Protein Binding: 73.99
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: 7.0
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.01
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.0
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: Toxic
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 3.91
Rat (Acute): 2.17
Rat (Chronic Oral): 3.2
Fathead Minnow: 3.99
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: 466.57
Hydration Free Energy: -12.51
Log(D) at pH=7.4: 2.25
Log(P): 2.28
Log S: -3.27
Log(Vapor Pressure): -7.69
Melting Point: 325.8
pKa Acid: 5.77
pKa Basic: 7.25

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9418
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9270
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9254
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9245
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.9117
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9086
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8795
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.8762
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.8746
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8744
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8739
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8676
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8665
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8644
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8636
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8612
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8544
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8511
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8464
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.8429
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8410
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8355
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8349
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.8275
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8257
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8241
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	4	0.8221
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8105
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8067
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8042
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.8030
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.7997
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7966
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7943
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7933
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7928
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7919
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7905
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7893
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	4	0.7879
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7858
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	4	0.7856
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7854
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7844
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7826
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7821
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7770
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7751
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7750
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7747
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7730
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7723
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7683
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7659
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7657
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7650
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7593
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7572
3',5'-cyclic-AMP phosphodiesterase 4A	P27815	PDE4A_HUMAN	Homo sapiens	4	0.7569
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7559
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7539
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	4	0.7516
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7516
Bifunctional dihydrofolate reductase-thymidylate synthase	A7UD81	A7UD81_PLAFA	Plasmodium falciparum	4	0.7514
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7502
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7497
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7489
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7488
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7488
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.7487
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7460
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7458
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7447
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7444
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7443
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7427
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7422
Bifunctional dihydrofolate reductase-thymidylate synthase	O02604	DRTS_PLAVI	Plasmodium vivax	3	0.7421
Odorant-binding protein	P81245	OBP_PIG	Sus scrofa	3	0.7404
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7381
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7374
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7343
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7319
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7316
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7300
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7296
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7283
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7268
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7267
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7265
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7251
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7225
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7214
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.7204
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	4	0.7200
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7187
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7185
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7182
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7173
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7173
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7171
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	4	0.7167
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7161
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7157
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7137
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7135
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7132
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7129
Bifunctional dihydrofolate reductase-thymidylate synthase	A7UD81	A7UD81_PLAFA	Plasmodium falciparum	3	0.7125
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7112
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7106
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.7098
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7093
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7087
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7083
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7073
Adenosine receptor A2a	P29274	AA2AR_HUMAN	Homo sapiens	4	0.7071
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7063
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7057
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7052
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7046
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7045
Maltokinase	A1TH50	MAK_MYCVP	Mycolicibacterium vanbaalenii	3	0.7042
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	5	0.7036
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7033
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7033
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7033
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7028
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7013
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.7002

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