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Isorhamnetin-3-O-rhamnoside

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

Canonical Smiles	COc1cc(ccc1O)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O
InChI	InChI=1S/C22H22O11/c1-8-16(26)18(28)19(29)22(31-8)33-21-17(27)15-12(25)6-10(23)7-14(15)32-20(21)9-3-4-11(24)13(5-9)30-2/h3-8,16,18-19,22-26,28-29H,1-2H3/t8-,16-,18+,19+,22-/m0/s1
InChIKey	UXXAEVMOIUAYQT-UFGFRKJLSA-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	Diplotaxis acris	Brassicaceae	Plantae	402674
2	Diplotaxis harra	Brassicaceae	Plantae	308281

Showing of synonyms

Hussein S.R, Marzouk M.M, et al. (2017). Chemosystematic significance of flavonoids isolated from Diplotaxis acris (Brassicaceae) and related taxa. Natural product research, 2017, 31(3), 347-350. [View] [PubMed]
Kassem M.E, Afifi M.S, et al. (2013). Two new flavonol glycosides and biological activities of Diplotaxis harra (Forssk.) Boiss. Natural product research, 2013, 27(24), 2272-80. [View] [PubMed]

Pubchem: 23634491

Cas: 67068-82-0

Zinc: ZINC000040412761

Nmrshiftdb2: 60005544

Chembl: CHEMBL485261

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 462.41 g/mol

SMILES: c1cccc(c12)occ(c2=O)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): -6.81
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.310
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.5

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.940
Plasma Protein Binding: 82.25
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: 14.870
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.830
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: 5.670
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: -107.920
Rat (Acute): 2.350
Rat (Chronic Oral): 3.890
Fathead Minnow: 4.000
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: 598.650
Hydration Free Energy: -4.050
Log(D) at pH=7.4: 1.190
Log(P): 1.26
Log S: -4.77
Log(Vapor Pressure): -10.52
Melting Point: 199.31
pKa Acid: 5.66
pKa Basic: 5.34

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9193
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9149
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9072
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8950
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8942
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8892
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8819
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8775
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8725
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8707
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8622
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8608
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8600
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8574
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8552
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8388
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8368
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8337
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8318
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8277
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8185
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8138
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8064
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.8063
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8007
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7944
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7939
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7932
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7932
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7921
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7916
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7897
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7896
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7892
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7866
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7854
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	7	0.7841
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7828
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7825
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7786
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7773
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7759
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7665
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7644
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7631
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	3	0.7620
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7610
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7600
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7584
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7540
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7534
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7530
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7509
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7421
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7386
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7372
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7350
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7294
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7291
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7245
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7236
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7235
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7218
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7212
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.7205
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7193
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7177
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7177
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7176
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7160
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7157
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7138
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7121
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7117
Kinesin heavy chain	Q41460	Q41460_SOLTU	Solanum tuberosum	3	0.7116
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7114
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7074
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7049
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7048
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7044
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7037
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7023
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7016
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7015
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7014
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7013
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7006

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