6-methoxyapigenin 7-glucoside - Compound Card

6-methoxyapigenin 7-glucoside

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6-methoxyapigenin 7-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Labiateae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles OCC1O[C@@H](Oc2cc3oc(cc(=O)c3c(c2OC)O)c2ccc(cc2)O)C([C@H]([C@@H]1O)O)O
InChI InChI=1S/C22H22O11/c1-30-21-14(32-22-20(29)19(28)17(26)15(8-23)33-22)7-13-16(18(21)27)11(25)6-12(31-13)9-2-4-10(24)5-3-9/h2-7,15,17,19-20,22-24,26-29H,8H2,1H3/t15?,17-,19+,20?,22-/m1/s1
InChIKey GCLAFEGUXXHIFT-PHBXNUNNSA-N
Formula C22H22O11
HBA 11
HBD 6
MW 462.41
Rotatable Bonds 5
TPSA 179.28
LogP 0.06
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 Phlomis aurea Lamiaceae Plantae 997702
2 Phlomis floccosa Lamiaceae Plantae 572125
3 Phlomis aurea Labiateae Plantae 997702
4 Phlomis floccosa Labiateae Plantae 572125

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: 44258433
Nmrshiftdb2: 60052302

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 462.41 g/mol

Structure

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

Level: 1

Mol. Weight: 462.41 g/mol

Structure

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

Level: 1

Mol. Weight: 462.41 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 462.41 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 462.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 462.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.54
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.19
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.99
Plasma Protein Binding
75.12
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
12.01
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.61
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.05
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.97
Micronucleos
Toxic
NR-AhR
Toxic
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
-127.42
Rat (Acute)
2.34
Rat (Chronic Oral)
3.72
Fathead Minnow
4.25
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
572.78
Hydration Free Energy
-3.62
Log(D) at pH=7.4
0.9
Log(P)
0.87
Log S
-4.63
Log(Vapor Pressure)
-11.24
Melting Point
212.53
pKa Acid
5.79
pKa Basic
4.61
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9572
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9497
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9170
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9127
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8997
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8880
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8786
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8772
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8728
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8688
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8674
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8673
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8664
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8580
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8491
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.8478
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8446
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8371
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8355
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8305
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8287
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8283
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8202
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8194
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8191
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8145
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8086
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8078
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8062
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8045
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8020
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7983
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7981
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7973
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7961
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7959
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7957
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7955
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7944
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7931
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7916
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7891
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7848
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7837
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7836
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7835
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7805
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7803
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7779
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7776
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7729
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7728
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7704
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7692
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7652
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7645
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7633
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7630
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7598
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7567
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7558
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7556
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7547
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7522
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7511
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.7509
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7502
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7474
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7449
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7393
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7391
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7378
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7369
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7350
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7331
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7322
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7314
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7303
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 4 0.7296
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 2 0.7296
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7295
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7278
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7272
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7264
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7261
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7259
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 5 0.7258
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 6 0.7255
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7249
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7212
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7207
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7180
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7179
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7166
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7154
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7152
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7140
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7140
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7134
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7122
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 4 0.7113
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 5 0.7111
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7107
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7078
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7076
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7054
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7046
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7042
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7035
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7030
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7026
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 4 0.7014
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7014
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7009

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