Isorhamnetin-3-O-[2′′′ O-acetyl-glucosyl (1→6)]-glucoside - Compound Card

Isorhamnetin-3-O-[2′′′ O-acetyl-glucosyl (1→6)]-glucoside

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Isorhamnetin-3-O-[2′′′ O-acetyl-glucosyl (1→6)]-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Brassicaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol
Canonical Smiles OC[C@@H]1OC(OC[C@@H]2OC(Oc3c(oc4c(c3=O)c(O)cc(c4)O)c3ccc(c(c3)OC)O)[C@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)OC(=O)C
InChI InChI=1S/C30H34O18/c1-10(32)44-28-24(40)20(36)17(8-31)46-30(28)43-9-18-21(37)23(39)25(41)29(47-18)48-27-22(38)19-14(35)6-12(33)7-16(19)45-26(27)11-3-4-13(34)15(5-11)42-2/h3-7,17-18,20-21,23-25,28-31,33-37,39-41H,8-9H2,1-2H3/t17-,18-,20-,21-,23+,24+,25-,28-,29?,30?/m0/s1
InChIKey RXXAOQSKAKEJKR-UFDCDGMOSA-N
Formula C30H34O18
HBA 18
HBD 9
MW 682.58
Rotatable Bonds 9
TPSA 284.73
LogP -1.84
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 48
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 682.17
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Diplotaxis acris Brassicaceae Plantae 402674

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]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 682.58 g/mol

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 682.58 g/mol

Structure

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

Level: 2

Mol. Weight: 682.58 g/mol

Structure

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

Level: 1

Mol. Weight: 682.58 g/mol

Structure

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

Level: 1

Mol. Weight: 682.58 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 682.58 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 682.58 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 682.58 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 682.58 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.63
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.99
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
78.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.81
Plasma Protein Binding
52.92
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
11.94
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.72
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.91
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.35
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
-140824.76
Rat (Acute)
2.3
Rat (Chronic Oral)
4.46
Fathead Minnow
193.15
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
7771.0
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-0.36
Log(P)
-0.58
Log S
-4.87
Log(Vapor Pressure)
-324.69
Melting Point
205.9
pKa Acid
3.97
pKa Basic
3.9
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 0.9215
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8972
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8911
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8795
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8741
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8704
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8668
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8416
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8398
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8312
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8275
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8136
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8043
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8032
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8029
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8014
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7967
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7923
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7914
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7910
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7909
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7823
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7724
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7722
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7707
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7692
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7599
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7539
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7521
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.7490
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7327
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7315
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7230
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7207
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7185
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7175
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7163
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7163
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7163
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 4 0.7158
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7157
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7097
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7084
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7066
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7050
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7033

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