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Hydroxyhispidin-di-O-glucoside

Family: Plantae - Tamaricaceae
Kingdom: Plantae
Class: Coumarin
- Subclass: Hydroxy Coumarin Glycoside

Canonical Smiles	OC[C@@H]1OC(Oc2cc(/C=C/c3cc(O)c(c(=O)o3)O)ccc2OC2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C25H30O16/c26-7-14-17(30)19(32)21(34)24(40-14)38-12-4-2-9(1-3-10-6-11(28)16(29)23(36)37-10)5-13(12)39-25-22(35)20(33)18(31)15(8-27)41-25/h1-6,14-15,17-22,24-35H,7-8H2/b3-1+/t14-,15+,17-,18+,19+,20-,21-,22+,24?,25?/m1/s1
InChIKey	JPRMVMFEAXALTA-XIUYWGNNSA-N
Formula	C₂₅H₃₀O₁₆
HBA	16
HBD	10
MW	586.5
Rotatable Bonds	8
TPSA	269.43
LogP	-3.42
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	41
Formal Charge	0
Fraction CSP3	0.48
Exact Mass	586.15
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Tamarix articulata	Tamaricaceae	Plantae	189786

Showing of synonyms

Shaalan Y.M, Handoussa H, et al. (2018). Destabilizing the interplay between miR-1275 and IGF2BPs by Tamarix articulata and quercetin in hepatocellular carcinoma. Nat Prod Res,2018,32(18),2217-2220. [View] [PubMed]

No compound-protein relationship available.

SMILES: O=c(o1)cccc1C=Cc2cc(OC3CCCCO3)c(cc2)OC4CCCCO4

Level: 3

Mol. Weight: 586.5 g/mol

SMILES: O=c(o1)cccc1C=Cc2ccc(cc2)OC3CCCCO3

Level: 2

Mol. Weight: 586.5 g/mol

SMILES: O=c(o1)cccc1C=Cc2cc(ccc2)OC3CCCCO3

Level: 2

Mol. Weight: 586.5 g/mol

SMILES: O1CCCCC1Oc2c(cccc2)OC3CCCCO3

Level: 2

Mol. Weight: 586.5 g/mol

SMILES: c1ccccc1C=Cc2cccc(=O)o2

Level: 1

Mol. Weight: 586.5 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 586.5 g/mol

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 586.5 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 586.5 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 586.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.62
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.46
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 2.81

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.83
Plasma Protein Binding: 59.27
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: 5.86
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.05
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.99
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.39
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: -4803.72
Rat (Acute): 2.29
Rat (Chronic Oral): 4.83
Fathead Minnow: 10.34
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 618.45
Hydration Free Energy: -3.13
Log(D) at pH=7.4: -2.18
Log(P): -3.77
Log S: -2.53
Log(Vapor Pressure): -13.9
Melting Point: 228.66
pKa Acid: 2.31
pKa Basic: 6.97

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9547
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9513
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9496
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9417
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9372
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.9221
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	3	0.9173
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9076
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8974
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8932
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.8816
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8814
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8805
LysR-type regulatory protein	Q7WT50	Q7WT50_9BURK	Burkholderia sp. DNT	3	0.8802
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8796
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8697
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8680
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8680
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	3	0.8658
Uric acid degradation bifunctional protein	Q45697	PUCL_BACSB	Bacillus sp	4	0.8654
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8626
Uracil-DNA glycosylase	P20536	UNG_VACCC	Vaccinia virus	4	0.8518
Uricase	Q00511	URIC_ASPFL	Aspergillus flavus	4	0.8440
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8437
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8422
Uricase	Q00511	URIC_ASPFL	Aspergillus flavus	4	0.8383
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8375
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8365
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.8335
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8307
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8281
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	3	0.8155
Catechol O-methyltransferase	P21964	COMT_HUMAN	Homo sapiens	3	0.8124
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8050
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8041
Uracil-DNA glycosylase	P9WFQ9	UNG_MYCTU	Mycobacterium tuberculosis	4	0.8023
Uracil-DNA glycosylase	P13051	UNG_HUMAN	Homo sapiens	4	0.8010
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7952
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7884
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7880
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7862
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7858
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7849
Thymidylate kinase	Q9KQI2	KTHY_VIBCH	Vibrio cholerae serotype O1	4	0.7843
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7837
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7836
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7835
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7824
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7822
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7802
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7800
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7728
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7680
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7676
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7673
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7658
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7622
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7613
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7607
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.7585
Nucleoside phosphorylase, putative	Q57VZ2	Q57VZ2_TRYB2	Trypanosoma brucei brucei	4	0.7572
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7570
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7564
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7554
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7540
Xanthine dehydrogenase/oxidase	P22985	XDH_RAT	Rattus norvegicus	3	0.7539
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7533
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7496
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7490
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7467
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7463
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7459
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	3	0.7437
Uridine phosphorylase	P12758	UDP_ECOLI	Escherichia coli	4	0.7411
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7388
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7370
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7367
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7360
Uridine phosphorylase	P0A1F6	UDP_SALTY	Salmonella typhimurium	3	0.7349
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7332
Monomeric sarcosine oxidase	P40859	MSOX_BACB0	Bacillus sp	3	0.7320
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7305
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7304
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7293
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7286
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	3	0.7281
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7273
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7266
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7247
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.7204
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7201
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7182
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7159
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7105
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7095
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7087
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7074
Purine nucleoside phosphorylase	B9JYS2	B9JYS2_AGRVS	Agrobacterium vitis	3	0.7070
Neutrophil gelatinase-associated lipocalin	P80188	NGAL_HUMAN	Homo sapiens	3	0.7065
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7051
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7030
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7026
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7020

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