2-hydroxy-4-methoxy-3,5-bis(3-methylbut-2- enyl)-6-phenethylbenzoic acid - Compound Card

2-hydroxy-4-methoxy-3,5-bis(3-methylbut-2- enyl)-6-phenethylbenzoic acid

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2-hydroxy-4-methoxy-3,5-bis(3-methylbut-2- enyl)-6-phenethylbenzoic acid

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles C(=O)(c1c(c(c(c(c1CCc1ccccc1)CC=C(C)C)OC)CC=C(C)C)O)O
InChI InChI=1S/C26H32O4/c1-17(2)11-14-21-20(16-13-19-9-7-6-8-10-19)23(26(28)29)24(27)22(25(21)30-5)15-12-18(3)4/h6-12,27H,13-16H2,1-5H3,(H,28,29)
InChIKey KTBAIBUBSGVINZ-UHFFFAOYSA-N
Formula C26H32O4
HBA 3
HBD 2
MW 408.54
Rotatable Bonds 9
TPSA 66.76
LogP 5.9
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 408.23
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Glycyrrhiza foetida Leguminosae/Fabaceae Plantae 512625

Showing of synonyms

  • Weidner C, Rousseau M, et al. (2016). Amorfrutin C Induces Apoptosis and Inhibits Proliferation in Colon Cancer Cells through Targeting Mitochondria. Journal of natural products, 2016, 79(1), 2-12. [View] [PubMed]
Pubchem: 45783216
Bindingdb: 50151924

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CCc2ccccc2

Level: 1

Mol. Weight: 408.54 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 408.54 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.16
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.650
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.290
Plasma Protein Binding
82.73
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
5.250
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.330
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.740
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.460
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
-12.560
Rat (Acute)
2.210
Rat (Chronic Oral)
3.620
Fathead Minnow
5.180
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
408.650
Hydration Free Energy
-5.090
Log(D) at pH=7.4
2.640
Log(P)
8.28
Log S
-4.9
Log(Vapor Pressure)
-9.31
Melting Point
150.04
pKa Acid
5.92
pKa Basic
6.82
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9263
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.9139
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.9027
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8967
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8813
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8675
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8426
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8418
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8411
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8394
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8210
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8168
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8155
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8134
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8107
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 4 0.8027
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7989
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7985
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7947
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7939
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7924
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7882
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7790
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7778
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7738
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7611
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7599
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7566
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7516
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7508
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7498
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7489
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7480
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7444
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7436
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7434
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7400
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7367
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7356
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7355
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7351
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7347
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 3 0.7326
Cytosol aminopeptidase P00727 AMPL_BOVIN Bos taurus 2 0.7319
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7312
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7310
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7282
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7282
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7261
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7259
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7256
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7252
Glutamate receptor ionotropic, kainate 1 P22756 GRIK1_RAT Rattus norvegicus 2 0.7240
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7232
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7217
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7214
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7174
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7163
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7156
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7149
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7138
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7125
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7113
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7110
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7107
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7103
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7095
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7083
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7082
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7057
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7052
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7045
Metabotropic glutamate receptor 7 Q14831 GRM7_HUMAN Homo sapiens 3 0.7041
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7028
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7014
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7005

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