3-O-acetyl chlorogenic acid - Compound Card

3-O-acetyl chlorogenic acid

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3-O-acetyl chlorogenic acid

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Glycoside
Canonical Smiles CC(=O)OC1CC(O)(CC(C1O)OC(=O)/C=C/c1ccc(c(c1)O)O)C(=O)O
InChI InChI=1S/C18H20O10/c1-9(19)27-13-7-18(26,17(24)25)8-14(16(13)23)28-15(22)5-3-10-2-4-11(20)12(21)6-10/h2-6,13-14,16,20-21,23,26H,7-8H2,1H3,(H,24,25)/b5-3+
InChIKey QFNRJVOIKSXASD-HWKANZROSA-N
Formula C18H20O10
HBA 9
HBD 5
MW 396.35
Rotatable Bonds 5
TPSA 170.82
LogP -0.08
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.39
Exact Mass 396.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Carissa edulis Apocynaceae Plantae 992661

Showing of synonyms

  • Al-Youssef HM and Hassan WHB. (2014). Chemical constituents of Carissa edulis Vahl. Arabian Journal of Chemistry,2014,in press. [View]

No compound-protein relationship available.

Structure

SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 396.35 g/mol

Structure

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 396.35 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 396.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.34
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.33
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.57
Plasma Protein Binding
-0.47
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
9.41
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.72
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.81
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.76
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
2.41
Rat (Acute)
2.05
Rat (Chronic Oral)
3.52
Fathead Minnow
3.93
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
449.23
Hydration Free Energy
-8.81
Log(D) at pH=7.4
-0.16
Log(P)
0.18
Log S
-2.03
Log(Vapor Pressure)
-10.92
Melting Point
203.41
pKa Acid
4.27
pKa Basic
5.24
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 0.9270
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9153
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9153
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9129
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9129
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9117
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9117
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.8992
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.8992
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8676
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8676
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8609
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8609
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.8455
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.8455
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8430
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8430
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8364
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8364
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8278
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8278
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 3 0.8257
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 3 0.8257
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8209
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8209
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8054
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8054
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8035
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8035
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.7969
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.7969
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7954
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7954
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7944
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7944
Nucleoside diphosphate kinase Q2SWE7 NDK_BURTA Burkholderia thailandensis 3 0.7912
Nucleoside diphosphate kinase Q2SWE7 NDK_BURTA Burkholderia thailandensis 3 0.7912
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7905
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7905
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7883
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7883
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7877
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7877
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7840
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7840
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7800
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7800
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7762
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7762
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7718
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7718
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7703
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7703
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7692
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7692
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7683
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7683
Ectonucleoside triphosphate diphosphohydrolase I Q5ZUA2 Q5ZUA2_LEGPH Legionella pneumophila subsp. pneumophila 3 0.7673
Ectonucleoside triphosphate diphosphohydrolase I Q5ZUA2 Q5ZUA2_LEGPH Legionella pneumophila subsp. pneumophila 3 0.7673
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7665
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7665
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7560
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7560
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7557
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7557
Shikimate dehydrogenase (NADP(+)) P56119 AROE_HELPY Helicobacter pylori 3 0.7531
Shikimate dehydrogenase (NADP(+)) P56119 AROE_HELPY Helicobacter pylori 3 0.7531
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7511
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7511
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7443
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7443
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7427
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7427
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7405
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7405
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7402
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7402
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7397
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7397
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7384
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7384
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7384
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7384
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7344
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7344
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7328
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7328
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7322
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7322
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7315
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7315
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7301
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7301
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
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7223
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7223
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7221
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7221
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7219
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7219
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7203
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7203
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7202
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7202
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7160
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7160
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7159
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7159
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7150
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7150
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7141
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7141
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7135
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7135
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 3 0.7125
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 3 0.7125
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7117
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
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7112
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7111
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7111
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7084
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7084
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7066
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7066
L-lactate dehydrogenase Q5SJA1 LDH_THET8 Thermus thermophilus 3 0.7057
L-lactate dehydrogenase Q5SJA1 LDH_THET8 Thermus thermophilus 3 0.7057
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7046
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7046
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7043
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7043
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7013
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7013
Probable bifunctional SAT/APS kinase O67174 SATC_AQUAE Aquifex aeolicus 3 0.7008
Probable bifunctional SAT/APS kinase O67174 SATC_AQUAE Aquifex aeolicus 3 0.7008
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7003
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7003

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