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6′-methoxy-2′,4-dihydroxychalcone -4′-O-beta-D-glucoside

Family: Plantae - Compositae
Kingdom: Plantae
Class: Chalcone

Canonical Smiles	OC[C@H]1O[C@@H](Oc2cc(O)c(c(c2)OC)C(=O)/C=C/c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C22H24O10/c1-30-16-9-13(31-22-21(29)20(28)19(27)17(10-23)32-22)8-15(26)18(16)14(25)7-4-11-2-5-12(24)6-3-11/h2-9,17,19-24,26-29H,10H2,1H3/b7-4+/t17-,19-,20+,21-,22-/m1/s1
InChIKey	VMXQTEKZPPIWMS-YKCILCNNSA-N
Formula	C₂₂H₂₄O₁₀
HBA	10
HBD	6
MW	448.42
Rotatable Bonds	7
TPSA	166.14
LogP	0.18
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	448.14
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Helichrysum foetidum	Compositae	Plantae	261783

Showing of synonyms

Malolo FA, Bissoue Nouga A, et al. (2015). Protease-inhibiting, molecular modeling and antimicrobial activities of extracts and constituents from Helichrysum foetidum and Helichrysum mechowianum (compositae).. Chemistry Central journal,2015, 9, 32. [View] [PubMed]

Pubchem: 10095186

Zinc: ZINC000033955938

Nmrshiftdb2: 70087065

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)c2ccc(cc2)OC3CCCCO3

Level: 2

Mol. Weight: 448.42 g/mol

SMILES: c1ccccc1C(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 448.42 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 448.42 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 448.42 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 448.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.66
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.220
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.75

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.860
Plasma Protein Binding: 77.5
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: 10.600
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.640
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.850
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.220
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: -61.290
Rat (Acute): 2.330
Rat (Chronic Oral): 4.020
Fathead Minnow: 4.340
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 545.780
Hydration Free Energy: -4.250
Log(D) at pH=7.4: 0.720
Log(P): 0.47
Log S: -4.37
Log(Vapor Pressure): -10.89
Melting Point: 179.41
pKa Acid: 5.59
pKa Basic: 4.3

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9447
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.9361
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.9261
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9224
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9150
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8899
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8862
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8656
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8590
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8492
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8405
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8363
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8361
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.8327
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.8249
Matrilysin	P09237	MMP7_HUMAN	Homo sapiens	3	0.8136
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8122
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.8116
Decaprenylphosphoryl-beta-D-ribose oxidase	I6X8C4	I6X8C4_MYCTU	Mycobacterium tuberculosis	3	0.8112
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.8108
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8107
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8096
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7996
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7986
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7980
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7963
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7945
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7936
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7891
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7822
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	4	0.7812
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7798
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7784
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7752
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7748
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.7742
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7724
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7707
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7702
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7701
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7689
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7687
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7679
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7669
C-1-tetrahydrofolate synthase, cytoplasmic	P11586	C1TC_HUMAN	Homo sapiens	4	0.7667
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7625
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7625
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7616
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7615
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7573
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7544
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7539
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7536
Ephrin type-A receptor 2	P29317	EPHA2_HUMAN	Homo sapiens	3	0.7480
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7478
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7462
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7459
Isoflavone-7-O-methyltransferase 8	O24529	7OMT8_MEDSA	Medicago sativa	5	0.7452
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7446
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7435
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7427
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7407
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7390
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7382
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7373
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7369
Uridine phosphorylase	Q5XA29	Q5XA29_STRP6	Streptococcus pyogenes serotype M6	3	0.7360
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7354
Isoliquiritigenin 2'-O-methyltransferase	P93324	CHOMT_MEDSA	Medicago sativa	3	0.7346
Ribonuclease TTHA0252	Q5SLP1	RNSE_THET8	Thermus thermophilus	3	0.7345
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7330
Polymerase basic protein 2	Q2LG68	Q2LG68_9INFA	Influenza A virus)	4	0.7327
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7305
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7305
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7291
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7279
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7276
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7276
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	3	0.7257
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7254
Formate--tetrahydrofolate ligase	Q2RM91	FTHS_MOOTA	Moorella thermoacetica	2	0.7250
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7239
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7235
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7205
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7195
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7194
Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	RET_HUMAN	Homo sapiens	3	0.7183
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	3	0.7172
Adenosine monophosphate-protein transferase	Q8ZVF7	Q8ZVF7_PYRAE	Pyrobaculum aerophilum	3	0.7162
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7149
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7149
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7143
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7140
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7127
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7124
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7122
Putative pteridine reductase 2	Q8I814	Q8I814_TRYCR	Trypanosoma cruzi	4	0.7098
Protein RecA	Q59560	RECA_MYCS2	Mycolicibacterium smegmatis155)	3	0.7089
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7081
Chromosome partitioning protein ParA	B0ZE06	B0ZE06_ECOLX	Escherichia coli	3	0.7073
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7071
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7068
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7047
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein	Q5SHN1	Q5SHN1_THET8	Thermus thermophilus	3	0.7044
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7036
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7034
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7025
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7019
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7018
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7005

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