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3-O-galloyl quinic acid

Family: Plantae - Anacardiaceae
Kingdom: Plantae
Class: Phenolic

Canonical Smiles	O[C@@H]1C[C@](O)(C[C@H]([C@@H]1O)OC(=O)c1cc(O)c(c(c1)O)O)C(=O)O
InChI	InChI=1S/C14H16O10/c15-6-1-5(2-7(16)10(6)18)12(20)24-9-4-14(23,13(21)22)3-8(17)11(9)19/h1-2,8-9,11,15-19,23H,3-4H2,(H,21,22)/t8-,9-,11-,14+/m1/s1
InChIKey	LDPLFHGGZNSKDS-FTBFGRRBSA-N
Formula	C₁₄H₁₆O₁₀
HBA	9
HBD	7
MW	344.27
Rotatable Bonds	3
TPSA	184.98
LogP	-1.34
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.43
Exact Mass	344.07
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Mangifera indica	Anacardiaceae	Plantae	29780

Showing of synonyms

Abdel-Mageed WM, Bayoumi SAH, et al. (2014). Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity. Bioorganic and Medicinal Chemistry,2014,22(7),2236-2243. [View] [PubMed]

Pubchem: 442988

Cas: 17365-11-6

Gnps: CCMSLIB00012176071

Zinc: ZINC000004098881

Kegg Ligand: C10834

Chebi: 9522

Nmrshiftdb2: 60028397

Chembl: CHEMBL3233512

Comptox: DTXSID60332031

CPRiL: 443905

SMILES: c1ccccc1C(=O)OC2CCCCC2

Level: 1

Mol. Weight: 344.27 g/mol

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 344.27 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 344.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.41
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.88
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.65

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.47
Plasma Protein Binding: 64.71
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: 6.34
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -3.04
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.76
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.25
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: 1.02
Rat (Acute): 1.73
Rat (Chronic Oral): 3.67
Fathead Minnow: 3.39
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: 478.36
Hydration Free Energy: -12.74
Log(D) at pH=7.4: -1.32
Log(P): -1.46
Log S: -1.42
Log(Vapor Pressure): -12.5
Melting Point: 188.35
pKa Acid: 4.0
pKa Basic: 8.11

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9260
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9260
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9099
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9099
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9009
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9009
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8752
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8752
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8651
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8651
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8608
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8608
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8519
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8519
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8493
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8493
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8492
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8492
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8448
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8448
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8446
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8446
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8416
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8416
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8399
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8399
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8241
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8241
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8212
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8212
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8170
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8170
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8144
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8144
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	4	0.8141
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	4	0.8141
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8105
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8105
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8062
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8062
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8040
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8040
CalS13	Q8KND8	Q8KND8_MICEC	Micromonospora echinospora	4	0.8018
CalS13	Q8KND8	Q8KND8_MICEC	Micromonospora echinospora	4	0.8018
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7968
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7968
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.7841
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.7841
2-dehydro-3-deoxyphosphooctonate aldolase	P0A715	KDSA_ECOLI	Escherichia coli	3	0.7811
2-dehydro-3-deoxyphosphooctonate aldolase	P0A715	KDSA_ECOLI	Escherichia coli	3	0.7811
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7810
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7810
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7751
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7751
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7740
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7740
Cytosolic IMP-GMP specific 5'-nucleotidase	Q5ZZB6	Q5ZZB6_LEGPH	Legionella pneumophila subsp. pneumophila	4	0.7705
Cytosolic IMP-GMP specific 5'-nucleotidase	Q5ZZB6	Q5ZZB6_LEGPH	Legionella pneumophila subsp. pneumophila	4	0.7705
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7677
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7677
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7658
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7658
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7657
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7657
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7619
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7619
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7612
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7612
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.7590
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.7590
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7564
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7564
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7550
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7550
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7547
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7547
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7489
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7489
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7475
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7475
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	5	0.7467
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	5	0.7467
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7451
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7451
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7448
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7448
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7420
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7420
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7407
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7407
Thymidylate synthase	P04818	TYSY_HUMAN	Homo sapiens	4	0.7367
Thymidylate synthase	P04818	TYSY_HUMAN	Homo sapiens	4	0.7367
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7354
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7354
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7346
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7346
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7345
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7345
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7318
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7318
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7293
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7293
Chromosome partitioning protein ParA	B0ZE06	B0ZE06_ECOLX	Escherichia coli	4	0.7268
Chromosome partitioning protein ParA	B0ZE06	B0ZE06_ECOLX	Escherichia coli	4	0.7268
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7265
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7265
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7259
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7259
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7243
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7243
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7217
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7217
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7197
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7197
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7187
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7187
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7167
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7167
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7166
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7166
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7152
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7152
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7149
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7149
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7133
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7133
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7122
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7122
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7097
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7097
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7092
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7092
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7069
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7069
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7060
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7060
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7056
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7056
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7044
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7044
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7006
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7006
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7002
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7002

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