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Isorhamnetin 5-glucoside

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Glycoside

Canonical Smiles	CCC1O[C@@H](Oc2cc(O)cc3c2c(=O)c(c(o3)c2ccc(c(c2)OC)O)O)C([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C23H24O11/c1-3-12-17(26)19(28)21(30)23(33-12)34-15-8-10(24)7-14-16(15)18(27)20(29)22(32-14)9-4-5-11(25)13(6-9)31-2/h4-8,12,17,19,21,23-26,28-30H,3H2,1-2H3/t12?,17-,19+,21?,23+/m1/s1
InChIKey	KOMHZTUOBVVDPX-JDVMTWNBSA-N
Formula	C₂₃H₂₄O₁₁
HBA	11
HBD	6
MW	476.43
Rotatable Bonds	5
TPSA	179.28
LogP	1.18
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	476.13
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Artemisia monosperma	Asteraceae	Plantae	72348
2	Artemisia monosperma	Asteraceae	Plantae	72348

Showing of synonyms

Saleh NAM, El-Newumy SI, et al. (1985). Flavonoid glycosides of Artemisia monosperma and A. herba-alba.. Phytochemistry,1985,24(1),201-203. [View]
Saleh NAM, El-Negoumy SI, et al. (1987). Flavonoids of Artemisia judaica, A. monosperma and A. Herba-alba.. Phytochemistry,1987,26(11),3059-3064. [View]

Pubchem: 44259378

Cas: 34199-20-7

Nmrshiftdb2: 60073366

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)cccc3OC4CCCCO4

Level: 2

Mol. Weight: 476.43 g/mol

SMILES: O=c1ccoc(c12)cccc2OC3CCCCO3

Level: 1

Mol. Weight: 476.43 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 476.43 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 476.43 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 476.43 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 476.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.76
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.32
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.3

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.02
Plasma Protein Binding: 78.27
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: 14.25
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.62
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.08
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.01
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: -187.83
Rat (Acute): 2.35
Rat (Chronic Oral): 3.87
Fathead Minnow: 4.24
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: 592.55
Hydration Free Energy: -3.83
Log(D) at pH=7.4: 1.01
Log(P): 0.48
Log S: -4.76
Log(Vapor Pressure): -10.63
Melting Point: 206.32
pKa Acid: 5.25
pKa Basic: 5.74

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9509
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9509
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9093
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9093
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9053
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9053
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9045
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9045
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9028
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9028
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8949
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8949
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8907
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8907
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8840
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8840
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8800
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8800
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8783
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8783
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8633
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8633
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8431
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8431
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8382
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8382
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8356
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8356
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8319
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8319
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8262
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8262
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8255
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8255
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.8161
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.8161
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8099
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8099
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8079
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8079
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.8072
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.8072
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7963
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7963
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7918
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7918
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7900
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7900
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7876
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7876
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.7846
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.7846
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7834
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7834
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7829
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7829
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7807
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7807
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7758
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7758
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7754
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7754
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7667
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7667
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7655
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7655
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7651
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7651
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7631
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7631
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7629
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7629
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7559
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7559
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7507
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7507
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	5	0.7430
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	5	0.7430
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7424
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7424
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7365
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7365
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7358
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7358
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7354
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7354
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7343
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7343
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7339
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7339
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7329
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7329
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7310
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7310
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7266
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7266
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7255
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7255
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7247
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7247
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7225
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7225
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7203
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7203
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7202
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7202
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.7191
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.7191
Laminarinase	Q9WXN1	Q9WXN1_THEMA	Thermotoga maritima	3	0.7175
Laminarinase	Q9WXN1	Q9WXN1_THEMA	Thermotoga maritima	3	0.7175
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.7165
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.7165
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7158
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7158
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7149
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7149
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7116
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7116
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7115
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7115
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7091
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7091
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.7087
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.7087
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7079
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7079
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7078
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7078
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7074
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7074
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	3	0.7069
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	3	0.7069
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7061
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7061
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7028
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7028
Putative secreted protein	C9Z6T8	C9Z6T8_STRSW	Streptomyces scabiei	4	0.7005
Putative secreted protein	C9Z6T8	C9Z6T8_STRSW	Streptomyces scabiei	4	0.7005
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7002
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7002

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