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[2,4-dihydroxy-6-(beta-D-glucopyranosyloxy)phenyl]-butan-1-one

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Tannin
- Subclass: Phloroglucinol Glycoside

Canonical Smiles	CCCC(=O)c1c(cc(cc1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C16H22O9/c1-2-3-8(19)12-9(20)4-7(18)5-10(12)24-16-15(23)14(22)13(21)11(6-17)25-16/h4-5,11,13-18,20-23H,2-3,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1
InChIKey	WVNHYQZOJMNKPX-YMILTQATSA-N
Formula	C₁₆H₂₂O₉
HBA	9
HBD	6
MW	358.34
Rotatable Bonds	6
TPSA	156.91
LogP	-0.74
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.56
Exact Mass	358.13
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Conyza aegyptiaca	Asteraceae	Plantae	741633

Showing of synonyms

Mahmouda AA, Al-Shihrya SS, et al. (2009). Biological activity of a phloroglucinol glucoside derivative from Conyza aegyptiaca. Zeitschrift fur Naturforschung C,2009,64,513-517. [View] [PubMed]

Pubchem: 51357548

Zinc: ZINC000095572401

Nmrshiftdb2: 70002616

Chembl: CHEMBL2152488

No compound-protein relationship available.

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 358.34 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 358.34 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 358.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.15
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.47
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.9

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.55
Plasma Protein Binding: 63.41
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-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: 9.13
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.58
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.73
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.76
Micronucleos: Toxic
NR-AhR: Safe
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: -1.14
Rat (Acute): 2.0
Rat (Chronic Oral): 3.95
Fathead Minnow: 3.69
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 489.83
Hydration Free Energy: -15.37
Log(D) at pH=7.4: 0.19
Log(P): 0.16
Log S: -2.46
Log(Vapor Pressure): -10.84
Melting Point: 152.22
pKa Acid: 4.85
pKa Basic: 7.06

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.9097
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.9097
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.9051
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.9051
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8780
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8780
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8297
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8297
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8172
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8172
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8021
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8021
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7996
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7996
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7922
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7922
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7896
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7896
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7883
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7883
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7864
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7864
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7828
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7828
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7816
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7816
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7727
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7727
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7679
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7679
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7679
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7679
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7671
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7671
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7659
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7659
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7647
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7647
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7644
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7644
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7638
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7638
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7619
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7619
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7613
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7613
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7500
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7500
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7457
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7457
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7455
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7455
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7436
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7436
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7360
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7360
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7290
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7290
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7250
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7250
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7249
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7249
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7232
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7232
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7229
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7229
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7217
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7217
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7186
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7186
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7181
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7181
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7164
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7164
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7159
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7159
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7130
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7130
Capsid protein VP1	O56137	O56137_9VIRU	Adeno-associated virus - 6	4	0.7076
Capsid protein VP1	O56137	O56137_9VIRU	Adeno-associated virus - 6	4	0.7076
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7026
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7026
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7026
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7026
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7010
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7010

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