Isorhamnetin-3-O-beta-D-glucosyl-7-O-alpha-L-rhamnoside - Compound Card

Isorhamnetin-3-O-beta-D-glucosyl-7-O-alpha-L-rhamnoside

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Isorhamnetin-3-O-beta-D-glucosyl-7-O-alpha-L-rhamnoside

Structure
Zoomed Structure
  • Family: Plantae - Resedaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone Glycoside
Canonical Smiles OC[C@@H]1O[C@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)c2ccc(c(c2)OC)O)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(40-9)41-11-6-13(31)17-15(7-11)42-25(10-3-4-12(30)14(5-10)39-2)26(20(17)34)44-28-24(38)22(36)19(33)16(8-29)43-28/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9-,16-,18-,19-,21+,22+,23+,24-,27-,28+/m0/s1
InChIKey NEJKEXUJCSYMCC-UJBZMDDSSA-N
Formula C28H32O16
HBA 16
HBD 9
MW 624.55
Rotatable Bonds 7
TPSA 258.43
LogP -1.74
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 44
Formal Charge 0
Fraction CSP3 0.46
Exact Mass 624.17
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Reseda villosa Resedaceae Plantae 415837

Showing of synonyms

  • Berrahal D, Kabouche A, et al. (2006). Flavonoid glycosides from Reseda villosa (Resedaceae). Biochemical Systematics and Ecology, 2006, 34(10), 777-779. [View]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(-c4ccccc4)c(c3=O)OC5CCCCO5

Level: 3

Mol. Weight: 624.55 g/mol

Structure

SMILES: O1CCCCC1Oc(cc2)cc(c23)occ(c3=O)OC4CCCCO4

Level: 2

Mol. Weight: 624.55 g/mol

Structure

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

Level: 2

Mol. Weight: 624.55 g/mol

Structure

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

Level: 2

Mol. Weight: 624.55 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 624.55 g/mol

Structure

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

Level: 1

Mol. Weight: 624.55 g/mol

Structure

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

Level: 1

Mol. Weight: 624.55 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 624.55 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 624.55 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 624.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.61
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.210
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
14.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.840
Plasma Protein Binding
71.72
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
9.730
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.550
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.960
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.600
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
-23584.520
Rat (Acute)
2.270
Rat (Chronic Oral)
4.660
Fathead Minnow
46.300
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
380.530
Hydration Free Energy
-2.930
Log(D) at pH=7.4
-0.410
Log(P)
-0.73
Log S
-4.65
Log(Vapor Pressure)
-17.33
Melting Point
230.59
pKa Acid
3.64
pKa Basic
5.51
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8873
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8852
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8782
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8587
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8584
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8572
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8341
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8282
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8166
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8159
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7963
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7890
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7794
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7794
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7741
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7730
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7728
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7692
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7689
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7683
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7646
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7503
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7478
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7474
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7423
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7386
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7355
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7334
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7330
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7329
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7326
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7321
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7319
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7226
Prothrombin P00734 THRB_HUMAN Homo sapiens 4 0.7217
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 4 0.7205
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7193
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7186
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7167
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7118
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7115
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7095
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7039

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