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5-O-caffeoylquinic acid

Family: Plantae - Hypericaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Benzophenone Glycoside

Canonical Smiles	O=C(OC1CC(O)(CC(C1O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
InChI	InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+
InChIKey	CWVRJTMFETXNAD-DUXPYHPUSA-N
Formula	C₁₆H₁₈O₉
HBA	8
HBD	6
MW	354.31
Rotatable Bonds	4
TPSA	164.75
LogP	-0.65
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	354.1
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Hypericum humifusum	Hypericaceae	Plantae	626746

Showing of synonyms

Rouis Z, Abid N, et al. (2013). Benzophenone glycosides from Hypericum humifusum ssp. austral. Journal of Natural Products,2013,76(5),979-982. [View] [PubMed]

Pubchem: 5315832

Cas: 534-61-2

Gnps: CCMSLIB00005467735

Chebi: 143036

Nmrshiftdb2: 60020307

Bindingdb: 153327

CPRiL: 69678

SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 354.31 g/mol

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 354.31 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 354.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.45
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.13
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.63

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.64
Plasma Protein Binding: 6.49
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: 6.47
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.12
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.63
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.15
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: 3.86
Rat (Acute): 1.87
Rat (Chronic Oral): 3.31
Fathead Minnow: 3.9
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: 452.62
Hydration Free Energy: -9.37
Log(D) at pH=7.4: -0.94
Log(P): -0.7
Log S: -1.31
Log(Vapor Pressure): -13.09
Melting Point: 193.73
pKa Acid: 3.26
pKa Basic: 7.03

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
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9150
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9150
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9114
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9114
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9059
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9059
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	3	0.8962
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	3	0.8962
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8781
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8781
3-dehydroquinate dehydratase	P9WPX7	AROQ_MYCTU	Mycobacterium tuberculosis	3	0.8700
3-dehydroquinate dehydratase	P9WPX7	AROQ_MYCTU	Mycobacterium tuberculosis	3	0.8700
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8664
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8664
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.8396
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.8396
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8390
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8390
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8365
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8365
Nucleoside diphosphate kinase	Q2SWE7	NDK_BURTA	Burkholderia thailandensis	3	0.8362
Nucleoside diphosphate kinase	Q2SWE7	NDK_BURTA	Burkholderia thailandensis	3	0.8362
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.8343
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.8343
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8209
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8209
Carboxyethyl-arginine beta-lactam-synthase	P0DJQ7	BLS_STRCL	Streptomyces clavuligerus	3	0.8165
Carboxyethyl-arginine beta-lactam-synthase	P0DJQ7	BLS_STRCL	Streptomyces clavuligerus	3	0.8165
Ectonucleoside triphosphate diphosphohydrolase I	Q5ZUA2	Q5ZUA2_LEGPH	Legionella pneumophila subsp. pneumophila	3	0.8119
Ectonucleoside triphosphate diphosphohydrolase I	Q5ZUA2	Q5ZUA2_LEGPH	Legionella pneumophila subsp. pneumophila	3	0.8119
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8062
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8062
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8056
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8056
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.8037
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.8037
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8018
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8018
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7930
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7930
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7918
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7918
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7884
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7884
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7770
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7770
Amino-acid acetyltransferase	Q5FAK7	Q5FAK7_NEIG1	Neisseria gonorrhoeae	3	0.7712
Amino-acid acetyltransferase	Q5FAK7	Q5FAK7_NEIG1	Neisseria gonorrhoeae	3	0.7712
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7653
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7653
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7624
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7624
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7605
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7605
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.7551
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.7551
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7538
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7538
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7478
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7478
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7422
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7422
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7421
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7421
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7418
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7418
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7393
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7393
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7387
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7387
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7386
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7386
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7374
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7374
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7346
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7346
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7345
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7345
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7341
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7341
Putative choline kinase	Q5CUP2	Q5CUP2_CRYPI	Cryptosporidium parvum	3	0.7340
Putative choline kinase	Q5CUP2	Q5CUP2_CRYPI	Cryptosporidium parvum	3	0.7340
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7338
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7338
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7294
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7294
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7227
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7227
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7213
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7213
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7212
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7212
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7201
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7201
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7180
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7180
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7178
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7178
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7173
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7173
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7148
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7148
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7135
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7135
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7135
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7135
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7132
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7132
Tryptophan--tRNA ligase	Q9PIB4	SYW_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7119
Tryptophan--tRNA ligase	Q9PIB4	SYW_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7119
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7116
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7116
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7077
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7077
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7077
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7077
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7068
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7068
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7044
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7044
Bifunctional protein GAL10	P04397	GAL10_YEAST	Saccharomyces cerevisiae	5	0.7042
Bifunctional protein GAL10	P04397	GAL10_YEAST	Saccharomyces cerevisiae	5	0.7042
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7030
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7030
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7026
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7026
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7016
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7016
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7015
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7015
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7003
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7003

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