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Chlorogenic acid butyl ester

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

Canonical Smiles	CCCCOC(=O)[C@]1(O)C[C@@H](O)[C@H]([C@@H](C1)OC(=O)C=Cc1ccc(c(c1)O)O)O
InChI	InChI=1S/C20H26O9/c1-2-3-8-28-19(26)20(27)10-15(23)18(25)16(11-20)29-17(24)7-5-12-4-6-13(21)14(22)9-12/h4-7,9,15-16,18,21-23,25,27H,2-3,8,10-11H2,1H3/t15-,16-,18-,20+/m1/s1
InChIKey	VNLREARKISTOAD-CIWUYKSXSA-N
Formula	C₂₀H₂₆O₉
HBA	9
HBD	5
MW	410.42
Rotatable Bonds	7
TPSA	153.75
LogP	0.61
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	410.16
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Thymelaea microphylla	Thymelaeaceae	Plantae	224056

Showing of synonyms

Kerbab K, Mekhelfi T, et al. (2015). Chemical composition and antioxidant activity of a polar extract of Thymelaea microphylla Coss. Et Dur. Nat Prod Res,2015,29(7),671-5. [View] [PubMed]

Pubchem: 6481825

No compound-protein relationship available.

SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 410.42 g/mol

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 410.42 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 410.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.99
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.89
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -2.01

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.64
Plasma Protein Binding: 64.89
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: 11.95
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.94
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.49
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.76
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -11.36
Rat (Acute): 2.0
Rat (Chronic Oral): 3.29
Fathead Minnow: 4.11
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 468.34
Hydration Free Energy: -11.34
Log(D) at pH=7.4: 1.48
Log(P): 1.76
Log S: -2.87
Log(Vapor Pressure): -9.19
Melting Point: 146.07
pKa Acid: 6.01
pKa Basic: 4.99

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	0.9346
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.9164
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9117
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.9074
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9073
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8851
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8804
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8802
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8797
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8795
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8757
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8719
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8626
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8615
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8547
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.8515
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8508
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8456
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.8425
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8407
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8367
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8281
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8249
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.8240
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8208
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8089
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8060
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8053
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8051
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7935
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7921
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7892
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7814
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7778
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7767
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7765
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7729
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7716
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7708
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7682
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7644
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	4	0.7639
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7629
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7611
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7559
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7501
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7495
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7465
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7451
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7420
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7407
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7373
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7372
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7366
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7347
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7346
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7345
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7334
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7323
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7316
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	3	0.7305
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7290
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7288
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7275
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7273
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7272
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7255
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7253
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7233
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7229
Purine nucleoside phosphorylase	Q9BMI9	Q9BMI9_SCHMA	Schistosoma mansoni	3	0.7211
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7211
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7205
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	2	0.7191
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7190
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7189
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	3	0.7186
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7184
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7181
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7179
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7170
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	3	0.7167
S-methyl-5'-thioinosine phosphorylase	Q9HZK1	MTIP_PSEAE	Pseudomonas aeruginosa	3	0.7167
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7166
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7164
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7160
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7150
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7146
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7130
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7129
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7122
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7112
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7107
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7107
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7100
Purine nucleoside phosphorylase 2	P45563	XAPA_ECOLI	Escherichia coli	3	0.7097
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7097
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7085
Sodium/potassium-transporting ATPase subunit alpha	Q4H132	Q4H132_SQUAC	Squalus acanthias	2	0.7070
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7061
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7061
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7051
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7049
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7047
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7045
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7033
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7031
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7030
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7021
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7014
Adenosylhomocysteinase	P10760	SAHH_RAT	Rattus norvegicus	5	0.7011
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7009
16S rRNA (adenine(1408)-N(1))-methyltransferase	A8C927	NPMA_ECOLX	Escherichia coli	3	0.7008
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7005
Holliday junction branch migration complex subunit RuvB	Q9PMT7	RUVB_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	2	0.7003
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7001

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