Caffeic acid-O-hexoside - Compound Card

Caffeic acid-O-hexoside

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Caffeic acid-O-hexoside

Structure
Zoomed Structure
  • Family: Lamiaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles OCC1OC(Oc2cc(/C=C/C(=O)O)ccc2O)C(C(C1O)O)O
InChI InChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(24-10)23-9-5-7(1-3-8(9)17)2-4-11(18)19/h1-5,10,12-17,20-22H,6H2,(H,18,19)/b4-2+
InChIKey QOPSZFXPZWQLOG-DUXPYHPUSA-N
Formula C15H18O9
HBA 8
HBD 6
MW 342.3
Rotatable Bonds 5
TPSA 156.91
LogP -1.33
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 342.1
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Rosmarinuseriocalyx Lamiaceae Plantae —

Showing of synonyms

  • Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]
Pubchem: 6124133

No compound-protein relationship available.

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 178.23 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.97
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.45
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.6
Plasma Protein Binding
2.58
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
6.76
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.81
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.59
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
1.23
Rat (Acute)
1.77
Rat (Chronic Oral)
3.73
Fathead Minnow
4.12
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
489.11
Hydration Free Energy
-15.42
Log(D) at pH=7.4
-2.55
Log(P)
-0.32
Log S
-1.67
Log(Vapor Pressure)
-10.73
Melting Point
165.85
pKa Acid
3.19
pKa Basic
5.79
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 3 0.9516
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8899
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.8728
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8645
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8489
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8381
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.8291
Adenylate cyclase 2 A0A2U2H3Y1 A0A384LKY8_YERPE Yersinia pestis 3 0.8248
Feruloyl esterase A O42807 FAEA_ASPNG Aspergillus niger 3 0.8223
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8057
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7943
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7828
Protein UshA P07024 USHA_ECOLI Escherichia coli 3 0.7827
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7722
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7702
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7657
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7657
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7654
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7642
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7626
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7625
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7582
Transcriptional regulator URE2 P23202 URE2_YEAST Saccharomyces cerevisiae 3 0.7493
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7478
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7453
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7433
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7427
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7426
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7409
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7408
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 4 0.7397
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7394
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7371
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7312
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7303
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7252
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7247
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7244
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7229
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7228
NTPase P4 Q94M05 Q94M05_9VIRU Pseudomonas phage phi12 3 0.7169
Metallophosphoesterase A3DJ38 A3DJ38_HUNT2 Clostridium thermocellum 2 0.7117
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7079
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7069
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7066
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7065
6-phosphogluconate dehydrogenase, decarboxylating P96789 6PGD_LACLM Lactococcus lactis subsp. cremoris 3 0.7062
Glutathione S-transferase Q8ILQ7 GST_PLAFA Plasmodium falciparum 3 0.7061
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7046
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7034
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7022
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7005
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7004

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