Apigenin 7-(6”-p-coumaroyl)glucoside - Compound Card

Apigenin 7-(6”-p-coumaroyl)glucoside

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Apigenin 7-(6”-p-coumaroyl)glucoside

Structure
Zoomed Structure
  • Family: Plantae - Labiateae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Lactoyl Flavonoid
Canonical Smiles O=C(OCC1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(cc2)O)C([C@H]([C@@H]1O)O)O)/C=C/c1ccc(cc1)O
InChI InChI=1S/C30H26O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-27(36)28(37)29(38)30(42-24)40-19-11-20(33)26-21(34)13-22(41-23(26)12-19)16-4-8-18(32)9-5-16/h1-13,24,27-33,36-38H,14H2/b10-3+/t24?,27-,28+,29?,30-/m1/s1
InChIKey WPQRDUGBKUNFJW-TUSHMLLXSA-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 Marrubium vulgare Lamiaceae Plantae 41230
2 Marrubium vulgare Labiateae Plantae 41230
3 Stachys aegyptiaca Lamiaceae Plantae 1391947
4 Stachys aegyptiaca Labiateae Plantae 1391947

Showing of synonyms

  • Nawwar M, El-Mousallamy A, et al. (1989). Flavonoid Lactates from Leaves of Marrubium Vulgare. Phytochemistry, 1989, 28(11), 3201-3206.. [View]
  • 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: 44257826

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)Oc(cc3)cc(c34)oc(cc4=O)-c5ccccc5

Level: 3

Mol. Weight: 578.53 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)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: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 578.53 g/mol

Structure

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

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)
-6.8
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.01
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
6.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.11
Plasma Protein Binding
81.39
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
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
8.7
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.38
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.03
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.86
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-11685.9
Rat (Acute)
2.38
Rat (Chronic Oral)
3.65
Fathead Minnow
31.29
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
475.31
Hydration Free Energy
-3.12
Log(D) at pH=7.4
2.73
Log(P)
3.1
Log S
-5.5
Log(Vapor Pressure)
-13.88
Melting Point
240.32
pKa Acid
6.97
pKa Basic
5.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9559
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9497
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9299
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9181
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9093
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9049
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8942
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8923
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8923
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8792
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8772
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8727
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8553
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8522
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8507
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8468
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8464
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8440
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8420
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.8418
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8376
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8374
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8371
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8362
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8297
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8286
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8274
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8249
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8214
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8161
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8152
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8133
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8131
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8091
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.8080
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8056
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8045
Beta sliding clamp P0A988 DPO3B_ECOLI Escherichia coli 3 0.8038
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8030
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8024
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.8022
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7964
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7957
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7956
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7949
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7940
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7938
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7919
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7915
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7915
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7894
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7884
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7882
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7851
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7839
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7831
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7784
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7776
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7762
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7748
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7736
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7723
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7707
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7690
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7679
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7662
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7640
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7623
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7566
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7551
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7538
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7534
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7525
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7513
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7509
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7503
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7501
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7486
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 3 0.7434
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7431
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7424
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7392
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7370
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7366
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7364
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 3 0.7363
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 3 0.7362
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7360
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7356
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7354
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7338
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7331
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7330
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 2 0.7325
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7324
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7320
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7317
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7311
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7299
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7290
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7286
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7282
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7259
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7249
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7244
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7241
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7237
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7233
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7231
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7227
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7226
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7214
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7213
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7209
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7209
Probable bifunctional SAT/APS kinase O67174 SATC_AQUAE Aquifex aeolicus 3 0.7205
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7198
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7195
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7175
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7170
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7165
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7151
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7141
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7127
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7116
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7110
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7107
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7097
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7095
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7090
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7088
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7079
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7073
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7070
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7065
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7064
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7061
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 3 0.7057
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7057
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7055
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7053
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7053
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7049
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7047
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7045
Nuclear receptor subfamily 5 group A member 2 O00482 NR5A2_HUMAN Homo sapiens 3 0.7038
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7035
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7030
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7029
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7029
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7026
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7009
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7009
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7008

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