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Chebulinic acid

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](COC(=O)c3cc(O)c(c(c3)O)O)O[C@H]([C@@H]([C@H]2OC(=O)c2cc(O)c(c(c2)O)O)OC(=O)c2c3[C@H]1[C@H](O)C(=O)Oc3c(c(c2)O)O)OC(=O)c1cc(O)c(c(c1)O)O
InChI	InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)/t14-,22+,24-,30-,31+,33-,34+,41-/m0/s1
InChIKey	YGVHOSGNOYKRIH-FJPMMHPYSA-N
Formula	C₄₁H₃₂O₂₇
HBA	26
HBD	13
MW	956.68
Rotatable Bonds	9
TPSA	447.09
LogP	0.02
Number Rings	7
Number Aromatic Rings	4
Heavy Atom Count	68
Formal Charge	0
Fraction CSP3	0.24
Exact Mass	956.11
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: 72284

Zinc: ZINC000195763592

Kegg Ligand: C10215

Chebi: 3584

CPRiL: 77312

SMILES: c1ccccc1C(=O)OC2C(OC3=O)C(OC(=O)c4ccccc4)OC(COC(=O)c5ccccc5)C2OC(=O)CC6CC(=O)Oc7cccc3c67

Level: 3

Mol. Weight: 956.68 g/mol

SMILES: c1ccccc1C(=O)OC2C(OC3=O)COC(COC(=O)c4ccccc4)C2OC(=O)CC5CC(=O)Oc6cccc3c56

Level: 2

Mol. Weight: 956.68 g/mol

SMILES: c1ccccc1C(=O)OC(C(C2)OC3=O)OC(COC(=O)c4ccccc4)C2OC(=O)CC5CC(=O)Oc6cccc3c56

Level: 2

Mol. Weight: 956.68 g/mol

SMILES: c1ccccc1C(=O)OC(OC2)C(OC3=O)C(OC(=O)c4ccccc4)C2OC(=O)CC5CC(=O)Oc6cccc3c56

Level: 2

Mol. Weight: 956.68 g/mol

SMILES: c1ccccc1C(=O)OCC(OCC(C2)OC3=O)C2OC(=O)CC4CC(=O)Oc5cccc3c45

Level: 1

Mol. Weight: 956.68 g/mol

SMILES: c1ccccc1C(=O)OC(OC2)C(OC3=O)CC2OC(=O)CC4CC(=O)Oc5cccc3c45

Level: 1

Mol. Weight: 956.68 g/mol

SMILES: c1ccccc1C(=O)OC(C(OC2=O)COC3)C3OC(=O)CC4CC(=O)Oc5cccc2c45

Level: 1

Mol. Weight: 956.68 g/mol

SMILES: c12c3cccc1OC(=O)CC2CC(=O)OC4CC(OC3=O)COC4

Level: 0

Mol. Weight: 956.68 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 956.68 g/mol

Antioxidant

Absorption

Caco-2 (logPapp): -6.52
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 6859.61
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 897338.5

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.43
Plasma Protein Binding: 21.67
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: 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: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 10.53
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -20863.13
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.16
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.05
Micronucleos: Toxic
NR-AhR: Toxic
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: -1628625209.81
Rat (Acute): 2.5
Rat (Chronic Oral): 6.98
Fathead Minnow: 2055802.73
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: 183163725.3
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -92.46
Log(P): -0.25
Log S: -5.84
Log(Vapor Pressure): -6031504.74
Melting Point: 362.76
pKa Acid: -43902.82
pKa Basic: -324.69

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9069
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9069
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	3	0.8992
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	3	0.8992
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.8891
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.8891
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8645
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8645
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8598
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8598
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8513
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8513
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8469
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8469
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.8468
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.8468
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8407
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8407
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8364
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8364
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8242
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8242
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8169
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8169
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8135
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8135
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8086
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8086
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8037
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8037
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8016
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8016
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.8015
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.8015
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7966
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7966
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7965
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7965
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7952
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7952
Alpha amylase	B8CZ54	B8CZ54_HALOH	Halothermothrix orenii	3	0.7939
Alpha amylase	B8CZ54	B8CZ54_HALOH	Halothermothrix orenii	3	0.7939
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7868
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7868
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7732
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7732
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7699
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7699
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7692
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7692
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7483
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7483
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7460
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7460
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7459
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7459
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7447
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7447
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7410
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7410
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7380
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7380
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7374
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7374
Neopullulanase 2	Q08751	NEPU2_THEVU	Thermoactinomyces vulgaris	3	0.7360
Neopullulanase 2	Q08751	NEPU2_THEVU	Thermoactinomyces vulgaris	3	0.7360
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	4	0.7360
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	4	0.7360
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7349
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7349
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7340
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7340
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7324
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7324
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7278
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7278
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	3	0.7261
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	3	0.7261
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7249
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7249
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7221
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7221
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7213
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7213
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7187
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7187
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7180
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7180
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7180
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7180
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7178
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7178
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	5	0.7144
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	5	0.7144
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7138
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7138
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7122
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7122
Nuclear receptor subfamily 5 group A member 2	O00482	NR5A2_HUMAN	Homo sapiens	3	0.7107
Nuclear receptor subfamily 5 group A member 2	O00482	NR5A2_HUMAN	Homo sapiens	3	0.7107
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7101
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7101
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7092
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7092
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7085
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7085
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.7065
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.7065
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7058
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7058
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	3	0.7058
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7058
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	3	0.7058
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7058
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7049
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7049
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7045
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7045
Acyl-CoA dehydrogenase, short-chain specific	Q06319	ACDS_MEGEL	Megasphaera elsdenii	4	0.7025
Acyl-CoA dehydrogenase, short-chain specific	Q06319	ACDS_MEGEL	Megasphaera elsdenii	4	0.7025

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