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Chlorogenic acid

Family: Plantae - Rosaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Phenolic Acid

Canonical Smiles	O=C(O[C@H]1C[C@](O)(C[C@@H]([C@@H]1O)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+/t11-,12-,14-,16+/m0/s1
InChIKey	CWVRJTMFETXNAD-KJOPMHRFSA-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	Crataegus azarolus	Rosaceae	Plantae	298644
2	Crataegus monogyna	Rosaceae	Plantae	140997

Showing of synonyms

Mraihi F, Hidalgo M, et al. (2015). Wild grown red and yellow hawthorn fruits from Tunisia as source of antioxidants. Arabian Journal of Chemistry, 2015, 8(4), 570-578. [View]

Pubchem: 12310830

Gnps: CCMSLIB00011430155

Zinc: ZINC000001532763

Nmrshiftdb2: 70128206

Chembl: CHEMBL366760

Bindingdb: 50540070

CPRiL: 1404

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): -6.47
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: -2.61

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.64
Plasma Protein Binding: 62.77
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: 6.29
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.33
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: 4.18
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: -0.41
Rat (Acute): 1.88
Rat (Chronic Oral): 3.28
Fathead Minnow: 3.87
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 456.53
Hydration Free Energy: -9.42
Log(D) at pH=7.4: -1.02
Log(P): -0.51
Log S: -1.34
Log(Vapor Pressure): -13.66
Melting Point: 203.13
pKa Acid: 3.23
pKa Basic: 7.02

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	0.9270
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9147
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9121
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9008
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8614
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	3	0.8586
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.8572
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8565
Putative choline kinase	Q5CUP2	Q5CUP2_CRYPI	Cryptosporidium parvum	3	0.8535
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.8465
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8362
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.8275
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8210
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8186
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.8122
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8112
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.8110
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8046
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8035
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7983
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7936
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7926
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7915
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7909
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7906
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7883
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase	P12995	BIOA_ECOLI	Escherichia coli	3	0.7819
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7816
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7806
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7780
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7779
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7736
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7675
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7668
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7648
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7623
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7575
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7507
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7501
Shikimate dehydrogenase (NADP(+))	P56119	AROE_HELPY	Helicobacter pylori	3	0.7472
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7450
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7433
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7411
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7386
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7364
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7336
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7323
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7298
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7273
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7248
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7227
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7214
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7210
5-formyltetrahydrofolate cyclo-ligase	P75430	MTHFS_MYCPN	Mycoplasma pneumoniae	2	0.7206
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7204
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1	Q9Y3Z3	SAMH1_HUMAN	Homo sapiens	3	0.7200
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	3	0.7199
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7199
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7198
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7193
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7166
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7144
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7119
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7117
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7112
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7108
Nucleoside diphosphate kinase	Q5SLV5	NDK_THET8	Thermus thermophilus	2	0.7081
Microcin C7 self-immunity protein MccF	Q47511	MCCF_ECOLX	Escherichia coli	3	0.7065
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	4	0.7057
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7044
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7029
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7015
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7004
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7003

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