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Cudraxanthone

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

Canonical Smiles	COc1cc2oc3c(O)cccc3c(=O)c2c(c1CC=C(C)C)O
InChI	InChI=1S/C19H18O5/c1-10(2)7-8-11-14(23-3)9-15-16(17(11)21)18(22)12-5-4-6-13(20)19(12)24-15/h4-7,9,20-21H,8H2,1-3H3
InChIKey	INFMYEMPDJIILH-UHFFFAOYSA-N
Formula	C₁₉H₁₈O₅
HBA	5
HBD	2
MW	326.35
Rotatable Bonds	3
TPSA	79.9
LogP	3.87
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.21
Exact Mass	326.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Hypericum roeperianum	Hypericaceae	Plantae	—

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]

Pubchem: 10449043

Cas: 77741-56-1

Zinc: ZINC000014819722

Chebi: 175157

Nmrshiftdb2: 60030274

Chembl: CHEMBL1224332

Bindingdb: 50325679

No compound-protein relationship available.

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

Level: 0

Mol. Weight: 326.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.7
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.650
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.18

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.250
Plasma Protein Binding: 64.77
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: Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 2.450
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.640
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.840
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.940
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: 3.590
Rat (Acute): 2.150
Rat (Chronic Oral): 2.810
Fathead Minnow: 5.260
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 440.510
Hydration Free Energy: -10.620
Log(D) at pH=7.4: 3.110
Log(P): 4.94
Log S: -5.79
Log(Vapor Pressure): -7.66
Melting Point: 161.18
pKa Acid: 7.05
pKa Basic: 6.09

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.9159
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9010
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.9006
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8922
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8848
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8771
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8738
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8615
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8587
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8529
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8317
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8243
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8220
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8213
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8207
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8180
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.8117
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.8111
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.8043
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.7987
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7984
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7977
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7977
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7964
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7898
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.7840
Bifunctional dihydrofolate reductase-thymidylate synthase	O02604	DRTS_PLAVI	Plasmodium vivax	3	0.7840
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7839
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7820
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7788
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7771
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7711
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7689
Biphenyl dioxygenase subunit alpha	P37333	BPHA_PARXL	Paraburkholderia xenovorans	3	0.7683
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7673
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7636
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7577
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7545
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7505
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7490
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7489
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7474
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7474
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7471
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7429
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7425
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7423
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7404
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7401
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7398
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7384
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	4	0.7351
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7346
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7341
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7341
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7335
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7299
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7283
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7264
Exotoxin A	P11439	TOXA_PSEAE	Pseudomonas aeruginosa	3	0.7261
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7258
Protein S100-A4	P26447	S10A4_HUMAN	Homo sapiens	3	0.7249
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7245
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7225
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7223
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7219
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7210
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7208
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7188
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7182
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.7173
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7163
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7150
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7149
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7126
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7111
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7110
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7105
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7104
Eukaryotic translation initiation factor 4E type 3	Q9DBB5	IF4E3_MOUSE	Mus musculus	3	0.7092
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7074
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7050
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	2	0.7043
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7036
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7030
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7027
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7020
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7017
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7017
ADP-ribosyl cyclase/cyclic ADP-ribose hydrolase 2	Q10588	BST1_HUMAN	Homo sapiens	4	0.7014
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7013
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7007

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