Apigenin 7-O-(3''-p-coumaryl) glucoside - Compound Card

Apigenin 7-O-(3''-p-coumaryl) glucoside

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Apigenin 7-O-(3''-p-coumaryl) glucoside

Structure
Zoomed Structure
  • Family: Plantae - Labiateae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles OCC1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(cc2)O)C([C@H]([C@@H]1O)OC(=O)/C=C/c1ccc(cc1)O)O
InChI InChI=1S/C30H26O12/c31-14-24-27(37)29(42-25(36)10-3-15-1-6-17(32)7-2-15)28(38)30(41-24)39-19-11-20(34)26-21(35)13-22(40-23(26)12-19)16-4-8-18(33)9-5-16/h1-13,24,27-34,37-38H,14H2/b10-3+/t24?,27-,28?,29+,30-/m1/s1
InChIKey JEOJQDYZOZKMAG-MXZSLGOPSA-N
Formula C30H26O12
HBA 12
HBD 6
MW 578.53
Rotatable Bonds 7
TPSA 196.35
LogP 2.02
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.2
Exact Mass 578.14
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Stachys aegyptiaca Lamiaceae Plantae 1391947
2 Stachys aegyptiaca Labiateae Plantae 1391947

Showing of synonyms

  • El-Ansari M, Nawwar M, et al. (1995). Stachysetin, A Diapigenin-7-Glucoside-p,p'-Dihydroxytruxinate from Stachys Aegyptiaca. Phytochemistry, 1995, 40(5),1543-1548.. [View]
Pubchem: 44257855

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)Oc(cc3)cc(c34)oc(cc4=O)-c5ccccc5

Level: 3

Mol. Weight: 578.53 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)Oc(cc3)cc(c34)occc4=O

Level: 2

Mol. Weight: 578.53 g/mol

Structure

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

Level: 2

Mol. Weight: 578.53 g/mol

Structure

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

Level: 1

Mol. Weight: 578.53 g/mol

Structure

SMILES: C1COCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 578.53 g/mol

Structure

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

Level: 1

Mol. Weight: 578.53 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 578.53 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 578.53 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 578.53 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.65
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
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
6.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.1
Plasma Protein Binding
82.77
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.14
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.11
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.99
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
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-11897.39
Rat (Acute)
2.47
Rat (Chronic Oral)
3.25
Fathead Minnow
32.08
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
475.05
Hydration Free Energy
-3.06
Log(D) at pH=7.4
2.75
Log(P)
2.84
Log S
-4.84
Log(Vapor Pressure)
-14.35
Melting Point
235.48
pKa Acid
7.25
pKa Basic
4.6
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9554
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9493
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9265
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9243
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9223
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9202
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9139
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.9138
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.9039
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9025
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.9001
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8934
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8896
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8836
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8810
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8800
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8798
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8742
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8724
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8666
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8664
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8664
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8582
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8530
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8475
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8472
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8447
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8429
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8416
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8406
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8341
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8330
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8310
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8299
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8292
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8243
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8234
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8202
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8197
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8196
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.8138
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.8097
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8025
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8014
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8010
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8009
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8006
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7991
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7977
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7968
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7930
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7893
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7883
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7869
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7783
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7769
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7769
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7746
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7720
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7719
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7700
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7662
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7662
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7647
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7645
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7631
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7626
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7622
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7590
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7576
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7574
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7536
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7530
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7525
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7516
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7515
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7514
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7509
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7502
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7499
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7489
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7472
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7449
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7433
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7421
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7417
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7417
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7407
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7385
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7333
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7332
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7331
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7330
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7329
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7322
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7321
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7312
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7312
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7287
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7278
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7269
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7256
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7255
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7255
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7254
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 2 0.7238
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7238
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7235
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7234
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7229
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7226
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7218
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7211
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7196
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7191
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7189
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7174
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7174
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7171
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7170
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7169
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7164
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7162
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7134
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7130
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7124
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7117
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7107
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.7103
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7102
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7100
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7098
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7092
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7090
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7084
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7072
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7060
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7058
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7056
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7055
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7049
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7046
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7046
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7043
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7039
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7038
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7026
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7021
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7015
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 3 0.7015
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7013
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7008
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7006
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7005
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7001

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