Apigenin 7-O-glucosyl-(1→2)-rhamnoside-(1→6)-glucoside - Compound Card

Apigenin 7-O-glucosyl-(1→2)-rhamnoside-(1→6)-glucoside

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Apigenin 7-O-glucosyl-(1→2)-rhamnoside-(1→6)-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Asparagaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles OCC1O[C@@H](OCC2O[C@@H](Oc3cc(O)c4c(c3)oc(cc4=O)c3ccc(cc3)O)C([C@H]([C@@H]2O)O)O[C@@H]2OC(C)[C@H](C([C@@H]2O)O)O)[C@H](C([C@@H]1O)O)O
InChI InChI=1S/C33H40O19/c1-11-22(38)25(41)29(45)32(47-11)52-30-27(43)24(40)20(10-46-31-28(44)26(42)23(39)19(9-34)50-31)51-33(30)48-14-6-15(36)21-16(37)8-17(49-18(21)7-14)12-2-4-13(35)5-3-12/h2-8,11,19-20,22-36,38-45H,9-10H2,1H3/t11?,19?,20?,22-,23-,24-,25?,26?,27+,28+,29+,30?,31-,32+,33-/m1/s1
InChIKey LXOPDILLGIDKLW-GKXMUKCTSA-N
Formula C33H40O19
HBA 19
HBD 11
MW 740.66
Rotatable Bonds 9
TPSA 308.12
LogP -3.27
Number Rings 6
Number Aromatic Rings 3
Heavy Atom Count 52
Formal Charge 0
Fraction CSP3 0.55
Exact Mass 740.22
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Hyacinthoides lingulata Asparagaceae Plantae 81761

Showing of synonyms

  • Hanfer M, Benramdane Z, et al. (2022). Chemical constituents, in vitro anti-inflammatory, antioxidant and hemostatic activities of the n butanol extract of Hyacinthoides lingulata (Poir.) Rothm. Natural product research, 2022, 36(12), 3124-3128. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)Oc(cc4)cc(c45)oc(cc5=O)-c6ccccc6

Level: 4

Mol. Weight: 740.66 g/mol

Structure

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)Oc(cc4)cc(c45)occc5=O

Level: 3

Mol. Weight: 740.66 g/mol

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(cc3)cc(c34)oc(cc4=O)-c5ccccc5

Level: 3

Mol. Weight: 740.66 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 740.66 g/mol

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(cc3)cc(c34)occc4=O

Level: 2

Mol. Weight: 740.66 g/mol

Structure

SMILES: O=c1ccoc(c12)cc(cc2)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 740.66 g/mol

Structure

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

Level: 2

Mol. Weight: 740.66 g/mol

Structure

SMILES: O1CCCCC1OCC2CCC(CO2)OC3CCCCO3

Level: 2

Mol. Weight: 740.66 g/mol

Structure

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

Level: 1

Mol. Weight: 740.66 g/mol

Structure

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

Level: 1

Mol. Weight: 740.66 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 740.66 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 740.66 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 740.66 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 740.66 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 740.66 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
-0.91
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
692.22

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.82
Plasma Protein Binding
42.4
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
5.74
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-14.76
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.68
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.3
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
-1252839.95
Rat (Acute)
2.5
Rat (Chronic Oral)
4.43
Fathead Minnow
1590.64
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
134273.48
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-0.71
Log(P)
-0.98
Log S
-4.35
Log(Vapor Pressure)
-4401.07
Melting Point
220.34
pKa Acid
-6.74
pKa Basic
5.85
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9493
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9466
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9238
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8926
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8746
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8710
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8657
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8445
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8352
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8343
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8278
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8115
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8042
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.8006
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8004
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.8000
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7940
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7934
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7904
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7886
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7830
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7767
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7750
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7642
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7603
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7579
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7565
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7550
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7522
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7497
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7463
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7402
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7357
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7343
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7298
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7259
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7196
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7183
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7173
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7172
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7152
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7149
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7117
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7114
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7100
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7086
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7068
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7060
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7052
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7014
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7009

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