Apigenin C-caffeoyl pentoside - Compound Card

Apigenin C-caffeoyl pentoside

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Apigenin C-caffeoyl pentoside

Structure
Zoomed Structure
  • Family: Plantae - Potamogetonaceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles OCC1OC(C(C1O)O)OC(=O)/C=C/c1ccc(c(c1)c1cc(O)c2c(c1)oc(cc2=O)c1ccc(cc1)O)O
InChI InChI=1S/C29H24O11/c30-13-24-27(36)28(37)29(39-24)40-25(35)8-2-14-1-7-19(32)18(9-14)16-10-20(33)26-21(34)12-22(38-23(26)11-16)15-3-5-17(31)6-4-15/h1-12,24,27-33,36-37H,13H2/b8-2+
InChIKey UJUIYTLJMOJADK-KRXBUXKQSA-N
Formula C29H24O11
HBA 11
HBD 6
MW 548.5
Rotatable Bonds 6
TPSA 187.12
LogP 2.24
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 548.13
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Potamogeton perfoliatus Potamogetonaceae Plantae 55320

Showing of synonyms

  • Rezq S, Mahmoud M.F, et al. (2021). Anti-Inflammatory, Antipyretic, and Analgesic Properties of Potamogeton perfoliatus Extract: In Vitro and In Vivo Study. Molecules, 2021, 26(16), 4826. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCC1OC(=O)C=Cc2cc(ccc2)-c(cc3)cc(c34)oc(cc4=O)-c5ccccc5

Level: 3

Mol. Weight: 548.5 g/mol

Structure

SMILES: O1CCCC1OC(=O)C=Cc2cc(ccc2)-c(cc3)cc(c34)occc4=O

Level: 2

Mol. Weight: 548.5 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)-c4ccccc4

Level: 2

Mol. Weight: 548.5 g/mol

Structure

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

Level: 1

Mol. Weight: 548.5 g/mol

Structure

SMILES: O=c1ccoc(c12)cc(cc2)-c3ccccc3

Level: 1

Mol. Weight: 548.5 g/mol

Structure

SMILES: O1CCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 548.5 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 548.5 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 548.5 g/mol

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 548.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.55
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.0
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
2.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.22
Plasma Protein Binding
63.01
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
7.0
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.02
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
6.39
Micronucleos
Toxic
NR-AhR
Toxic
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
-5128.35
Rat (Acute)
2.54
Rat (Chronic Oral)
3.56
Fathead Minnow
18.0
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
548.38
Hydration Free Energy
-3.04
Log(D) at pH=7.4
2.65
Log(P)
3.44
Log S
-4.31
Log(Vapor Pressure)
-9.6
Melting Point
242.04
pKa Acid
7.26
pKa Basic
6.09
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 0.9495
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9286
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9263
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9174
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9149
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9053
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9029
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8982
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8974
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8966
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8949
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8910
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8855
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8853
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8841
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8743
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8714
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.8688
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8653
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8600
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8530
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8515
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8497
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8444
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.8440
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8433
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8433
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8428
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8396
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8338
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8330
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.8327
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8311
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8257
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8243
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8200
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8140
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8104
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8066
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8059
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8053
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8029
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8025
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8013
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7995
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7969
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7958
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7956
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7915
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7885
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7868
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7811
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7802
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7796
Kelch-like ECH-associated protein 1 Q14145 KEAP1_HUMAN Homo sapiens 3 0.7795
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7780
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7777
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7776
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7758
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7734
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7712
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7699
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7686
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7664
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7662
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7651
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 4 0.7647
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7642
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7621
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7609
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 4 0.7603
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7596
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 2 0.7595
Fumarate reductase subunit D P0A8Q3 FRDD_ECOLI Escherichia coli 3 0.7593
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7591
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7588
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7573
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7571
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7556
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7537
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 4 0.7534
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7531
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7528
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7500
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7498
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7484
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7477
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7473
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7449
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7448
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7440
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7425
Renin P00797 RENI_HUMAN Homo sapiens 5 0.7404
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7392
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7383
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 3 0.7375
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7374
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7367
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7360
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.7350
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7349
Probable bifunctional SAT/APS kinase O67174 SATC_AQUAE Aquifex aeolicus 3 0.7348
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7347
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7336
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7326
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7324
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7316
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7308
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7299
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7296
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7285
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7285
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7285
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7283
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7248
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7225
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7225
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7219
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7209
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7209
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7203
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7188
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7185
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7182
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7173
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7173
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7170
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7165
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7164
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic P49235 HGGL1_MAIZE Zea mays 2 0.7163
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7148
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7135
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7134
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7126
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7106
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7085
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 3 0.7084
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7081
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7071
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7070
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7064
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7062
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7060
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7057
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7055
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7052
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7051
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7045
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7044
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 4 0.7043
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7039
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7039
Tyrosine-protein kinase ABL1 P00519 ABL1_HUMAN Homo sapiens 3 0.7033
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7026
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7008

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