Benzoic acid 2,3-diacetoxy-1,6-dihydroxycyclohex-4-enylmethyl ester - Compound Card

Benzoic acid 2,3-diacetoxy-1,6-dihydroxycyclohex-4-enylmethyl ester

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Benzoic acid 2,3-diacetoxy-1,6-dihydroxycyclohex-4-enylmethyl ester

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles CC(=O)OC1C(C=CC(C1(O)COC(=O)c1ccccc1)O)OC(=O)C
InChI InChI=1S/C18H20O8/c1-11(19)25-14-8-9-15(21)18(23,16(14)26-12(2)20)10-24-17(22)13-6-4-3-5-7-13/h3-9,14-16,21,23H,10H2,1-2H3
InChIKey MAIHNXWUKKJTIY-UHFFFAOYSA-N
Formula C18H20O8
HBA 8
HBD 2
MW 364.35
Rotatable Bonds 5
TPSA 119.36
LogP 0.37
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.39
Exact Mass 364.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Uvaria pandensis Annonaceae Plantae 673193

Showing of synonyms

  • Maeda G, Gilissen PJ, et al. (2021). Oxygenated Cyclohexene Derivatives from the Stem and Root Barks of Uvaria pandensis. Journal of natural products,2021, 84(12), 3080-3089. [View] [PubMed]
Pubchem: 76448852

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OCC2CC=CCC2

Level: 1

Mol. Weight: 364.35 g/mol

Structure

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 364.35 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 364.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.11
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.55
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.07

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.4
Plasma Protein Binding
-2.74
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
6.14
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.04
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.64
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.04
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
0.14
Rat (Acute)
2.35
Rat (Chronic Oral)
2.91
Fathead Minnow
4.08
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
363.11
Hydration Free Energy
-9.56
Log(D) at pH=7.4
0.89
Log(P)
1.08
Log S
-2.53
Log(Vapor Pressure)
-7.47
Melting Point
122.57
pKa Acid
6.28
pKa Basic
0.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9539
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8753
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8645
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8501
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8485
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.8283
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8183
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8144
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8018
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7998
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7987
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7926
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7924
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7899
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7897
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 4 0.7790
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7691
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7644
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7640
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7613
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7603
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7512
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7427
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7399
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7361
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7292
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7274
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7265
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7256
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7239
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7223
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7190
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7184
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7148
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7118
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7106
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7093
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7060
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7035
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7026
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7001

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