Chebulagic acid - Compound Card

Chebulagic acid

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Chebulagic acid

Structure
Zoomed Structure
  • Family: Plantae - Combretaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Chebulic Ellagitannin
Canonical Smiles OC(=O)C[C@@H]1C(=O)O[C@@H]2[C@H]3COC(=O)c4cc(O)c(c(c4c4c(C(=O)O[C@@H]2[C@@H](OC(=O)c2c5[C@H]1[C@H](O)C(=O)Oc5c(c(c2)O)O)[C@@H](O3)OC(=O)c1cc(O)c(c(c1)O)O)cc(O)c(c4O)O)O)O
InChI InChI=1S/C41H30O27/c42-13-1-8(2-14(43)24(13)49)35(56)68-41-34-33-31(64-39(60)12(6-19(47)48)22-23-11(38(59)67-34)5-17(46)27(52)32(23)65-40(61)30(22)55)18(63-41)7-62-36(57)9-3-15(44)25(50)28(53)20(9)21-10(37(58)66-33)4-16(45)26(51)29(21)54/h1-5,12,18,22,30-31,33-34,41-46,49-55H,6-7H2,(H,47,48)/t12-,18+,22-,30-,31+,33-,34+,41-/m0/s1
InChIKey HGJXAVROWQLCTP-YABCKIEDSA-N
Formula C41H30O27
HBA 26
HBD 13
MW 954.66
Rotatable Bonds 4
TPSA 447.09
LogP -0.0
Number Rings 8
Number Aromatic Rings 4
Heavy Atom Count 68
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 954.1
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: 442674
Kegg Ligand: C10214
Chebi: 3583
Nmrshiftdb2: 60028483
Bindingdb: 50366290
CPRiL: 100846
Structure

SMILES: c1cccc(c1c23)C(=O)OCC4C5C(OC(=O)c2cccc3)C(C(O4)OC(=O)c6ccccc6)OC(=O)c7c8c(ccc7)OC(=O)CC8CC(=O)O5

Level: 1

Mol. Weight: 954.66 g/mol

Structure

SMILES: c1cccc(c1c23)C(=O)OCC4C5C(OC(=O)c2cccc3)C(CO4)OC(=O)c6c7c(ccc6)OC(=O)CC7CC(=O)O5

Level: 0

Mol. Weight: 954.66 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 954.66 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-6.47
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
8672.05
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1134258.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.44
Plasma Protein Binding
16.11
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
Inhibitor

Excretion

Clearance
9.99
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-26372.12
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.3
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.05
Micronucleos
Toxic
NR-AhR
Toxic
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
-2058619247.63
Rat (Acute)
2.56
Rat (Chronic Oral)
7.31
Fathead Minnow
2598578.54
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
231526016.31
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-121.78
Log(P)
-0.75
Log S
-5.53
Log(Vapor Pressure)
-7624050.96
Melting Point
381.48
pKa Acid
-55518.77
pKa Basic
-415.36
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8144
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8144
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8106
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8106
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7983
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7983
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7827
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7827
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7783
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7783
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 4 0.7716
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 4 0.7716
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7696
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7696
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7679
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7679
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7657
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7657
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7558
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7558
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7458
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7458
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7404
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7404
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7293
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7293
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7281
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7281
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7254
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7254
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7243
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7243
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7208
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7208
Nuclear receptor subfamily 5 group A member 2 O00482 NR5A2_HUMAN Homo sapiens 3 0.7135
Nuclear receptor subfamily 5 group A member 2 O00482 NR5A2_HUMAN Homo sapiens 3 0.7135
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7062
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7062
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7038
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7038
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7004
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7004

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