Naringenin 7-glucoside - Compound Card

Naringenin 7-glucoside

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Naringenin 7-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles OCC1OC(Oc2cc3OC(CC(=O)c3c(c2)O)c2ccc(cc2)O)C(C(C1O)O)O
InChI InChI=1S/C21H22O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-6,14,16,18-24,26-28H,7-8H2
InChIKey DLIKSSGEMUFQOK-UHFFFAOYSA-N
Formula C21H22O10
HBA 10
HBD 6
MW 434.4
Rotatable Bonds 4
TPSA 166.14
LogP -0.02
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 434.12
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Phlomis aurea Lamiaceae Plantae 997702

Showing of synonyms

  • El-Negoumy S, Abdalla M, et al. (1986). Flavonoids of Phlomis Aurea and P. Floccosa. Phytochemistry, 1986, 25(3), 772-774.. [View]
Pubchem: 282013
Nmrshiftdb2: 60021657

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(CC2=O)Oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 434.4 g/mol

Structure

SMILES: O=C1CCOc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 434.4 g/mol

Structure

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 434.4 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 434.4 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 434.4 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 434.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.82
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.23
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.88
Plasma Protein Binding
14.29
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
12.88
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.99
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.67
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.67
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
-46.29
Rat (Acute)
2.36
Rat (Chronic Oral)
3.85
Fathead Minnow
4.27
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
544.48
Hydration Free Energy
-5.53
Log(D) at pH=7.4
0.7
Log(P)
0.15
Log S
-3.7
Log(Vapor Pressure)
-11.69
Melting Point
203.22
pKa Acid
5.21
pKa Basic
6.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9451
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9404
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9296
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.9145
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8870
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8850
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8842
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8825
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8688
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8687
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.8661
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8608
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8598
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8569
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8567
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8500
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8491
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8462
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8360
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8293
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8270
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8251
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8249
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8188
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8186
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8175
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8162
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8145
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8143
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8133
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8036
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7975
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7880
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7838
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7820
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7814
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7790
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7786
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7784
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7775
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7767
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7682
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7629
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7556
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7556
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7549
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7519
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7518
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7508
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7475
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7460
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7454
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7433
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7421
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7341
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7288
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7283
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7266
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7247
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7227
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7213
6-phosphogluconate dehydrogenase, decarboxylating P96789 6PGD_LACLM Lactococcus lactis subsp. cremoris 3 0.7202
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7178
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7163
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7162
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7159
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7159
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7146
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7137
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.7133
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7123
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7111
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7093
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7080
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7054
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7046
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7033
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7022

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