(-)-shikimic acid-4-O-gallate - Compound Card

(-)-shikimic acid-4-O-gallate

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(-)-shikimic acid-4-O-gallate

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Polyphenol
Canonical Smiles OC1CC(=CC(C1OC(=O)c1c(C)cc(c(c1O)O)O)O)C(=O)O
InChI InChI=1S/C15H16O9/c1-5-2-7(16)11(19)12(20)10(5)15(23)24-13-8(17)3-6(14(21)22)4-9(13)18/h2-3,8-9,13,16-20H,4H2,1H3,(H,21,22)
InChIKey IJBOJSLRPYVMTA-UHFFFAOYSA-N
Formula C15H16O9
HBA 8
HBD 6
MW 340.28
Rotatable Bonds 3
TPSA 164.75
LogP -0.23
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 340.08
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia helioscopia Euphorbiaceae Plantae 154990

Showing of synonyms

  • Mohamed AH, Hegazy MF, et al. (2012). Euphorbia helioscopia: Chemical constituents and biological activities. International Journal of Phytopharmacology,2012,3(1),78-90. [View]
Pubchem: 163044300

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC2CC=CCC2

Level: 1

Mol. Weight: 340.28 g/mol

Structure

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 340.28 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 340.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.33
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.380
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-4.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.640
Plasma Protein Binding
20.39
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
8.830
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.770
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.190
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.830
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
7.120
Rat (Acute)
1.840
Rat (Chronic Oral)
3.230
Fathead Minnow
3.900
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
462.020
Hydration Free Energy
-9.120
Log(D) at pH=7.4
-1.490
Log(P)
-0.15
Log S
-1.56
Log(Vapor Pressure)
-11.18
Melting Point
167.33
pKa Acid
4.09
pKa Basic
6.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8877
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8877
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8873
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8873
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8828
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8828
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 3 0.8659
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 3 0.8659
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8537
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8537
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 3 0.8480
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 3 0.8480
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 4 0.8458
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 4 0.8458
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8435
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8435
dTDP-4-dehydro-6-deoxyglucose 3-epimerase Q5SFD1 CHMJ_STRBI Streptomyces bikiniensis 4 0.8383
dTDP-4-dehydro-6-deoxyglucose 3-epimerase Q5SFD1 CHMJ_STRBI Streptomyces bikiniensis 4 0.8383
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 4 0.8352
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 4 0.8352
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8321
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8321
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7991
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7991
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.7986
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.7986
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7927
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7927
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7924
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7924
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7907
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7907
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7902
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7902
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7859
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7859
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 5 0.7846
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 5 0.7846
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7825
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7825
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.7820
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.7820
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7807
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7807
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7805
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7805
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7776
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7776
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7738
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7738
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7724
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7724
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7663
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7663
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7639
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7639
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7601
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7601
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7598
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7598
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7577
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7577
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 4 0.7555
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 4 0.7555
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7545
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7545
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 6 0.7542
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 6 0.7542
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7517
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7517
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.7513
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.7513
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7491
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7491
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7455
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7455
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7431
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7431
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7402
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7402
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 6 0.7370
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 6 0.7370
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7363
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7363
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7327
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7327
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7325
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7325
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7313
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7313
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7294
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7294
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7280
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7280
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7249
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7249
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7247
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7247
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 5 0.7247
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 5 0.7247
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7210
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7210
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7204
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7204
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7197
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7197
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7189
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7189
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7181
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7181
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 5 0.7178
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 5 0.7178
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7164
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7164
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7163
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7163
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7156
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7156
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7139
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7139
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7130
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7130
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7124
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7124
MutT/nudix family protein O33199 O33199_MYCTO Mycobacterium tuberculosis 3 0.7114
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7114
MutT/nudix family protein O33199 O33199_MYCTO Mycobacterium tuberculosis 3 0.7114
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7114
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7112
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7112
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7108
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7108
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7096
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7096
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7084
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7084
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7078
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7078
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7061
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7061
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7058
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7058
Chaperone protein HtpG P0A6Z3 HTPG_ECOLI Escherichia coli 3 0.7049
Chaperone protein HtpG P0A6Z3 HTPG_ECOLI Escherichia coli 3 0.7049
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase Q9WY79 MURE_THEMA Thermotoga maritima 3 0.7028
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase Q9WY79 MURE_THEMA Thermotoga maritima 3 0.7028
Decapping and exoribonuclease protein O70348 DXO_MOUSE Mus musculus 3 0.7022
Decapping and exoribonuclease protein O70348 DXO_MOUSE Mus musculus 3 0.7022

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