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Isorhamnetin 7-O-alpha-L-rhamnopyranoside

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

Canonical Smiles	COc1cc(ccc1O)c1oc2cc(O[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)cc(c2c(=O)c1O)O
InChI	InChI=1S/C22H22O11/c1-8-16(25)18(27)20(29)22(31-8)32-10-6-12(24)15-14(7-10)33-21(19(28)17(15)26)9-3-4-11(23)13(5-9)30-2/h3-8,16,18,20,22-25,27-29H,1-2H3/t8-,16-,18+,20+,22-/m0/s1
InChIKey	XLQFMBLUUSGXQY-FDTPGTFWSA-N
Formula	C₂₂H₂₂O₁₁
HBA	11
HBD	6
MW	462.41
Rotatable Bonds	4
TPSA	179.28
LogP	0.79
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	462.12
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Moricandia nitens	Brassicaceae	Plantae	264187

Showing of synonyms

Marzouk M.M, Al-Nowaihi A.S.M, et al. (2010). Chemosystematic studies on certain species of the family Brassicaceae(Cruciferae) in Egypt. Biochemical Systematics and Ecology, 2010, 38(4), 680–685.. [View]

Pubchem: 102007835

Cas: 17331-72-5

Zinc: ZINC000238773562

Nmrshiftdb2: 60071194

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 462.41 g/mol

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 462.41 g/mol

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

Level: 1

Mol. Weight: 462.41 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 462.41 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 462.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 462.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.64
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.270
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.2

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.030
Plasma Protein Binding: 85.82
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: 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: 13.700
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.590
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.150
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.730
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: -110.720
Rat (Acute): 2.360
Rat (Chronic Oral): 3.940
Fathead Minnow: 4.090
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: 585.090
Hydration Free Energy: -3.790
Log(D) at pH=7.4: 0.880
Log(P): 0.32
Log S: -4.85
Log(Vapor Pressure): -10.82
Melting Point: 214.83
pKa Acid: 5.38
pKa Basic: 4.85

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9670
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9530
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9315
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9278
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9175
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9145
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.9081
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9080
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9049
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9031
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8957
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8905
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8899
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8898
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	5	0.8871
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8870
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8842
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.8803
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8783
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8780
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8722
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.8665
Cyclin-dependent kinase 5	Q00535	CDK5_HUMAN	Homo sapiens	5	0.8550
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.8525
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8514
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.8458
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8457
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8412
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8407
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8392
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.8365
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8351
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8344
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8311
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8299
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8296
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	5	0.8253
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8230
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.8206
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8196
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8193
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8184
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.8112
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8103
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8093
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8092
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8090
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8080
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8078
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8049
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8034
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8020
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8020
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8016
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7983
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7927
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7917
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7905
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7903
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7890
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7883
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7870
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7865
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7853
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7843
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.7836
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7834
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7826
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	4	0.7802
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7767
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7764
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7760
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7753
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7751
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7735
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7692
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7684
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7662
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7658
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7644
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7643
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7641
Catalase-peroxidase	Q3JNW6	KATG_BURP1	Burkholderia pseudomallei	3	0.7634
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7632
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7624
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7622
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7591
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7590
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.7580
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7540
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7536
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7535
Laminarinase	Q9WXN1	Q9WXN1_THEMA	Thermotoga maritima	3	0.7506
Cyclin-dependent kinase 6	Q00534	CDK6_HUMAN	Homo sapiens	5	0.7493
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7489
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7477
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7457
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	3	0.7453
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7452
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	4	0.7438
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	5	0.7432
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7413
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7397
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7385
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	4	0.7368
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7364
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7363
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7356
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7343
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7342
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7333
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7327
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	3	0.7318
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7306
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7298
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7295
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7295
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7293
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7271
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7271
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7271
Beta-glucosidase 12	B8AVF0	BGL12_ORYSI	Oryza sativa subsp. indica	3	0.7267
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7258
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7254
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7252
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7232
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7228
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7225
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7217
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7211
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7195
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7187
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7186
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	4	0.7186
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7181
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7172
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7145
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7138
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7128
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	4	0.7125
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7110
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	5	0.7106
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7105
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7104
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7101
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7090
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7069
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7064
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7044
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7044
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7043
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7030
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7024
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.7022
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7007
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7001

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