Gallagic acid - Compound Card

Gallagic acid

Select a section from the left sidebar

Gallagic acid

Structure
Zoomed Structure
  • Family: Plantae - Combretaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Ellagic Acid Derivative
Canonical Smiles Oc1cc2c(=O)oc3c(c2c(c1O)O)c1c(=O)oc2c4c1c(c3O)oc(=O)c4c1c(c2O)oc(=O)c2c1c(O)c(O)c(c2)O
InChI InChI=1S/C28H10O16/c29-5-1-3-7(17(33)15(5)31)9-13-11-12-14(28(40)44-23(11)19(35)21(9)41-25(3)37)10-8-4(2-6(30)16(32)18(8)34)26(38)42-22(10)20(36)24(12)43-27(13)39/h1-2,29-36H
InChIKey UGAJKWZVPNVCIO-UHFFFAOYSA-N
Formula C28H10O16
HBA 16
HBD 8
MW 602.37
Rotatable Bonds 0
TPSA 282.68
LogP 2.65
Number Rings 8
Number Aromatic Rings 8
Heavy Atom Count 44
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 602.0
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Terminalia species Combretaceae Plantae 39992

Showing of synonyms

  • Pfundstein B, El Desouky SK, et al. (2010). Polyphenolic compounds in the fruits of Egyptian medicinal plants (Terminalia bellerica, Terminalia chebula and Terminalia horrida): Characterization, quantitation and determination of antioxidant capacities. Phytochemistry,2010,71(10),1132-1148. [View] [PubMed]
Pubchem: 5281711
Kegg Ligand: C10242
Chebi: 9454
Nmrshiftdb2: 60064616

No compound-protein relationship available.

Structure

SMILES: c12c3c4c5c6c(cccc6)c(=O)oc5cc3oc(=O)c1c7c8c(cccc8)c(=O)oc7cc2oc4=O

Level: 0

Mol. Weight: 602.37 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-5.98
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.410
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
28.4

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.320
Plasma Protein Binding
77.25
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
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
8.450
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.010
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.310
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.370
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-44597.970
Rat (Acute)
2.300
Rat (Chronic Oral)
4.270
Fathead Minnow
81.400
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
431.100
Hydration Free Energy
-3.170
Log(D) at pH=7.4
0.460
Log(P)
1.52
Log S
-4.86
Log(Vapor Pressure)
-43.26
Melting Point
513.22
pKa Acid
9.65
pKa Basic
2.0
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8742
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8742
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8572
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8572
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8540
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8540
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7989
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7989
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7958
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7958
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7958
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7958
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7651
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7651
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7637
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7637
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7561
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7561
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7529
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7529
Uricase Q00511 URIC_ASPFL Aspergillus flavus 4 0.7460
Uricase Q00511 URIC_ASPFL Aspergillus flavus 4 0.7460
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.7451
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.7451
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7425
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7425
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 4 0.7355
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 4 0.7355
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.7277
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.7277
Protease Q5RTL1 Q5RTL1_9HIV1 Human immunodeficiency virus 1 4 0.7275
Protease Q5RTL1 Q5RTL1_9HIV1 Human immunodeficiency virus 1 4 0.7275
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7267
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7267
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7257
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7257
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7192
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7192
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7178
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7178
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7109
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7109
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 3 0.7097
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 3 0.7097
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7075
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7075
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7074
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7074
Serine/threonine-protein kinase PAK 4 O96013 PAK4_HUMAN Homo sapiens 4 0.7074
Serine/threonine-protein kinase PAK 4 O96013 PAK4_HUMAN Homo sapiens 4 0.7074

Download SDF