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1,5-dihydroxy-8-methoxyxanthone

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

Canonical Smiles	COc1ccc(c2c1c(=O)c1c(o2)cccc1O)O
InChI	InChI=1S/C14H10O5/c1-18-9-6-5-8(16)14-12(9)13(17)11-7(15)3-2-4-10(11)19-14/h2-6,15-16H,1H3
InChIKey	HUYOUKKMFHFSIU-UHFFFAOYSA-N
Formula	C₁₄H₁₀O₅
HBA	5
HBD	2
MW	258.23
Rotatable Bonds	1
TPSA	79.9
LogP	2.37
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	19
Formal Charge	0
Fraction CSP3	0.07
Exact Mass	258.05
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: 86088977

Zinc: ZINC000014822000

Nmrshiftdb2: 60070195

No compound-protein relationship available.

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

Level: 0

Mol. Weight: 258.23 g/mol

Antibacterial

Absorption

Caco-2 (logPapp): -4.81
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.560
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.04

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.160
Plasma Protein Binding: 73.69
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: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 3.980
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.200
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.020
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.140
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 4.700
Rat (Acute): 2.160
Rat (Chronic Oral): 2.630
Fathead Minnow: 4.620
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 415.770
Hydration Free Energy: -11.030
Log(D) at pH=7.4: 2.720
Log(P): 3.31
Log S: -4.37
Log(Vapor Pressure): -7.32
Melting Point: 199.52
pKa Acid: 6.72
pKa Basic: 4.74

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.9643
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9307
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9304
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.9164
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9016
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.8991
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8835
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8758
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8749
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8749
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8738
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8737
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8727
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.8725
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8720
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.8680
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8667
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.8652
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	4	0.8649
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8633
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8619
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8562
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8502
Bifunctional dihydrofolate reductase-thymidylate synthase	O02604	DRTS_PLAVI	Plasmodium vivax	3	0.8472
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.8445
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8397
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8311
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8238
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8236
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.8171
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.8105
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	3	0.8099
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8095
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.8094
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.8091
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8063
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.8061
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8034
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8031
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8025
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7998
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7997
Cobalt-precorrin-4 C(11)-methyltransferase	O87696	CBIF_BACME	Priestia megaterium	3	0.7958
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.7942
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7901
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7900
Putative HMP/thiamine-binding protein YkoF	O34911	YKOF_BACSU	Bacillus subtilis	3	0.7894
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7882
Odorant-binding protein	P81245	OBP_PIG	Sus scrofa	3	0.7858
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7843
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7837
Biphenyl dioxygenase subunit alpha	P37333	BPHA_PARXL	Paraburkholderia xenovorans	3	0.7825
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7806
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7792
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7744
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7681
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	3	0.7664
Catalase-peroxidase	Q3JNW6	KATG_BURP1	Burkholderia pseudomallei	3	0.7653
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7652
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7636
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7633
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7606
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7604
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7592
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	3	0.7575
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7573
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7556
Glycylpeptide N-tetradecanoyltransferase	Q4Q5S8	Q4Q5S8_LEIMA	Leishmania major	3	0.7543
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7540
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7525
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7510
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.7488
Pyridoxal kinase	P82197	PDXK_SHEEP	Ovis aries	3	0.7484
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7480
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7478
Ras-related protein Rap-1b	P61224	RAP1B_HUMAN	Homo sapiens	4	0.7474
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7447
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7443
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7442
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7440
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7439
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q3JRA0	ISPF_BURP1	Burkholderia pseudomallei	4	0.7438
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7427
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7404
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7400
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7395
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7372
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7342
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7337
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7328
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7323
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7312
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7296
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7294
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7282
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.7271
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	3	0.7260
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7259
Tyrosine-protein kinase HCK	P08631	HCK_HUMAN	Homo sapiens	3	0.7249
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7244
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7243
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7243
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7241
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7239
DNA mismatch repair protein MutS	P23909	MUTS_ECOLI	Escherichia coli	3	0.7236
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7227
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7223
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7206
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7205
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7197
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7190
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7186
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7184
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7182
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7178
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7175
Aklavinone 12-hydroxylase RdmE	Q54530	DNRF_STREF	Streptomyces purpurascens	4	0.7174
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7173
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7155
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7147
7,8-dihydroneopterin aldolase	J7VEZ6	J7VEZ6_BACCE	Bacillus cereus BAG3X2-1	3	0.7127
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7123
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7122
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	2	0.7116
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7107
SRSF protein kinase 1	Q96SB4	SRPK1_HUMAN	Homo sapiens	3	0.7103
Nicotinamide riboside kinase 1	Q9NWW6	NRK1_HUMAN	Homo sapiens	3	0.7097
Dimethylglycine dehydrogenase, mitochondrial	Q63342	M2GD_RAT	Rattus norvegicus	4	0.7094
Exotoxin A	P11439	TOXA_PSEAE	Pseudomonas aeruginosa	3	0.7094
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7080
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7068
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7058
Maltokinase	A1TH50	MAK_MYCVP	Mycolicibacterium vanbaalenii	3	0.7055
Aspartokinase 1, chloroplastic	Q9LYU8	AK1_ARATH	Arabidopsis thaliana	3	0.7048
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7038
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7032
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	3	0.7029
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7029
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7028
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7027
Activated CDC42 kinase 1	Q07912	ACK1_HUMAN	Homo sapiens	3	0.7027
Bifunctional dihydrofolate reductase-thymidylate synthase	O02604	DRTS_PLAVI	Plasmodium vivax	3	0.7025
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7012
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q02127	PYRD_HUMAN	Homo sapiens	3	0.7011
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7003
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7002

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