ANPDB

Select a section from the left sidebar

8,10-dihydroxy-3-(4hydroxy-3,5-dimethoxyphenyl-2-(hydroxymethyl)-2,3-dihydro-[1,4]dioxino[2,3-c]xanthen-7-one

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

Canonical Smiles	OC[C@@H]1Oc2c(O[C@H]1c1cc(OC)c(c(c1)OC)O)ccc1c2oc2cc(O)cc(c2c1=O)O
InChI	InChI=1S/C24H20O10/c1-30-16-5-10(6-17(31-2)21(16)29)22-18(9-25)34-24-14(32-22)4-3-12-20(28)19-13(27)7-11(26)8-15(19)33-23(12)24/h3-8,18,22,25-27,29H,9H2,1-2H3/t18-,22-/m0/s1
InChIKey	ZIXRDOIIRHBBIP-AVRDEDQJSA-N
Formula	C₂₄H₂₀O₁₀
HBA	10
HBD	4
MW	468.41
Rotatable Bonds	4
TPSA	148.05
LogP	2.95
Number Rings	5
Number Aromatic Rings	4
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.21
Exact Mass	468.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	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]

Pubchem: 162852391

Zinc: ZINC000013381027

Nmrshiftdb2: 70132053

No compound-protein relationship available.

SMILES: c1cccc(c2=O)c1oc(c23)c4c(cc3)OC(CO4)c5ccccc5

Level: 1

Mol. Weight: 468.41 g/mol

SMILES: O1CCOc(cc2)c1c(c23)oc4c(c3=O)cccc4

Level: 0

Mol. Weight: 468.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 468.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.87
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.020
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.04

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.350
Plasma Protein Binding: 70.59
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-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: 8.860
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.260
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.000
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.950
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: -289.590
Rat (Acute): 2.230
Rat (Chronic Oral): 3.170
Fathead Minnow: 5.540
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 582.180
Hydration Free Energy: -2.990
Log(D) at pH=7.4: 2.340
Log(P): 2.61
Log S: -6.15
Log(Vapor Pressure): -10.21
Melting Point: 244.69
pKa Acid: 6.94
pKa Basic: 2.25

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9522
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9303
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9281
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9233
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9223
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.9063
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9039
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.9038
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9037
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8845
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8834
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8773
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8692
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8682
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8592
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8467
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8465
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.8424
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8419
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8398
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8343
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8288
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8274
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	4	0.8265
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.8250
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8195
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8178
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8159
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8120
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8115
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8063
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8023
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.7996
Dihydrofolate reductase	O30463	O30463_MYCAV	Mycobacterium avium	4	0.7970
Cyclin-dependent kinase 6	Q00534	CDK6_HUMAN	Homo sapiens	3	0.7899
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7842
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7800
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7762
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	4	0.7755
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7707
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7675
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7660
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7646
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7553
Uracil-DNA glycosylase	P13051	UNG_HUMAN	Homo sapiens	4	0.7549
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7545
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7538
Odorant-binding protein	P81245	OBP_PIG	Sus scrofa	3	0.7506
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7498
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7496
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7480
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7443
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7439
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7436
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7327
tRNA (adenine(9)-N1)-methyltransferase	Q4J894	TRM10_SULAC	Sulfolobus acidocaldarius	4	0.7325
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	4	0.7309
Thymidylate synthase ThyA	P9WFR9	TYSY_MYCTU	Mycobacterium tuberculosis	3	0.7307
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7295
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.7284
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7268
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7263
Rho family GTPase	C4M4W4	C4M4W4_ENTHI	Entamoeba histolytica	4	0.7248
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7233
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7231
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7212
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7193
DNA mismatch repair protein MutS	P23909	MUTS_ECOLI	Escherichia coli	3	0.7166
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7150
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7150
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7135
Glucose-1-phosphate thymidylyltransferase 1	P37744	RMLA1_ECOLI	Escherichia coli	5	0.7130
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7129
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	3	0.7114
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7110
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	4	0.7103
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7097
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7066
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7055
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7049
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7046
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7039
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7033
Uracil-DNA glycosylase	P9WFQ9	UNG_MYCTU	Mycobacterium tuberculosis	4	0.7024

Download SDF