4-O-(4'- carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid - Compound Card

4-O-(4'- carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid

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4-O-(4'- carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid

Structure
Zoomed Structure
  • Family: Convolvulaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Hydroxybenzoic Acid
Canonical Smiles COc1cc(ccc1OC1C(O)CC(CC1O)(O)CC(=O)O)C(=O)O
InChI InChI=1S/C16H20O9/c1-24-12-4-8(15(21)22)2-3-11(12)25-14-9(17)5-16(23,6-10(14)18)7-13(19)20/h2-4,9-10,14,17-18,23H,5-7H2,1H3,(H,19,20)(H,21,22)
InChIKey LJQISQWYZYQLHL-UHFFFAOYSA-N
Formula C16H20O9
HBA 7
HBD 5
MW 356.33
Rotatable Bonds 6
TPSA 153.75
LogP -0.14
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 356.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Convolvulus dorycnium Convolvulaceae Plantae 267580

Showing of synonyms

  • Nacef S, Jannet H, et al. (2010). Phenolic constituents of Convolvulus dorycnium L. flowers. Phytochemistry Letters, 2010, 3(2), 66-69. [View]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1OC2CCCCC2

Level: 1

Mol. Weight: 176.26 g/mol

Structure

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 84.16 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.26
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.030
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.500
Plasma Protein Binding
13.89
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
3.210
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.590
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.630
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.840
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
4.320
Rat (Acute)
1.900
Rat (Chronic Oral)
3.580
Fathead Minnow
3.950
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
404.430
Hydration Free Energy
-9.560
Log(D) at pH=7.4
-3.120
Log(P)
-0.03
Log S
-2.08
Log(Vapor Pressure)
-12.08
Melting Point
200.14
pKa Acid
2.96
pKa Basic
6.62
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.9393
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9126
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.8669
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8650
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.8611
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8513
Probable nicotinate-nucleotide adenylyltransferase Q9HX21 NADD_PSEAE Pseudomonas aeruginosa 3 0.8443
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8389
Bis(5'-adenosyl)-triphosphatase P49789 FHIT_HUMAN Homo sapiens 3 0.8355
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 4 0.8310
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8195
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.8182
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8179
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8156
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8140
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.8140
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8123
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8065
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7955
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7954
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7951
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7878
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7798
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 3 0.7677
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7661
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7596
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7534
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7527
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 4 0.7511
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7508
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7507
Fatty acid-binding protein 2, liver P81400 FABP2_AMBME Ambystoma mexicanum 3 0.7439
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7419
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7381
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7315
Serine/threonine-protein kinase RAD53 P22216 RAD53_YEAST Saccharomyces cerevisiae 4 0.7314
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7310
GMP reductase Q81JJ9 GUAC_BACAN Bacillus anthracis 3 0.7252
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7243
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7222
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7220
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7213
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7204
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7180
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7170
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 2 0.7159
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7150
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7148
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7141
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7138
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7134
Carbonic anhydrase Q39588 Q39588_CHLRE Chlamydomonas reinhardtii 3 0.7133
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7116
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7113
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7087
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7075
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7049
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 3 0.7045
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7036
5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase Q8U0R7 PURP_PYRFU Pyrococcus furiosus 3 0.7032
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7006
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7002

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