2-(2-hydroxy-3-methylbut-3-enyl)-4-(3-methylbut-2-enyl)-5-pentylbenzene- 1,3-diol - Compound Card

2-(2-hydroxy-3-methylbut-3-enyl)-4-(3-methylbut-2-enyl)-5-pentylbenzene- 1,3-diol

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2-(2-hydroxy-3-methylbut-3-enyl)-4-(3-methylbut-2-enyl)-5-pentylbenzene- 1,3-diol

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles CCCCCc1cc(O)c(c(c1CC=C(C)C)O)CC(C(=C)C)O
InChI InChI=1S/C21H32O3/c1-6-7-8-9-16-12-20(23)18(13-19(22)15(4)5)21(24)17(16)11-10-14(2)3/h10,12,19,22-24H,4,6-9,11,13H2,1-3,5H3
InChIKey PDNBFWVCEQNNBO-UHFFFAOYSA-N
Formula C21H32O3
HBA 3
HBD 3
MW 332.48
Rotatable Bonds 9
TPSA 60.69
LogP 4.82
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 332.24
Number of Lipinski Rule Violations 0
# 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: 144740322

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 332.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.64
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.31

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.59
Plasma Protein Binding
37.92
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.11
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.72
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.06
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.11
Micronucleos
Safe
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
3.36
Rat (Acute)
2.01
Rat (Chronic Oral)
2.67
Fathead Minnow
4.38
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
355.58
Hydration Free Energy
-7.91
Log(D) at pH=7.4
3.67
Log(P)
5.78
Log S
-4.8
Log(Vapor Pressure)
-6.69
Melting Point
82.65
pKa Acid
9.87
pKa Basic
6.67
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.9440
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.9300
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9160
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.9117
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9097
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8993
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8875
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8862
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8854
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8847
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8818
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8582
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8568
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8483
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8462
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8416
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8389
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8324
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8298
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8257
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.8188
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8144
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.8107
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8070
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8029
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7995
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7991
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7971
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7971
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7944
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7924
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7872
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7841
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7832
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7828
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7821
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7821
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7810
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7799
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7725
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7710
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7702
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7692
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7668
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7624
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7610
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7608
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7591
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7551
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7544
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7487
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7481
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7475
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7466
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7463
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7441
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7413
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7410
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7376
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7361
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7355
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7342
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7334
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7325
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7323
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7316
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7311
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7300
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7290
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7280
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7264
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7251
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7248
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7232
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7207
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7207
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7195
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7174
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7156
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7148
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7130
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7113
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7102
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7093
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7084
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7057
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7055
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7039
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7038
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 2 0.7033
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7032
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7026
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7026
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7017
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7012
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7008

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