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

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

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

Structure
Zoomed Structure
  • Family: Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles c1(c(c(c(c(c1)CCc1ccccc1)CC=C(C)C)O)CC(C(=C)C)O)O
InChI InChI=1S/C24H30O3/c1-16(2)10-13-20-19(12-11-18-8-6-5-7-9-18)14-23(26)21(24(20)27)15-22(25)17(3)4/h5-10,14,22,25-27H,3,11-13,15H2,1-2,4H3
InChIKey NHQPTPUMTXSDEV-UHFFFAOYSA-N
Formula C24H30O3
HBA 3
HBD 3
MW 366.5
Rotatable Bonds 8
TPSA 60.69
LogP 4.87
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 366.22
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: 45783219

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CCc2ccccc2

Level: 1

Mol. Weight: 182.27 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.99
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.69
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.08

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.98
Plasma Protein Binding
60.36
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
5.73
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.79
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.17
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.37
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
-0.11
Rat (Acute)
2.16
Rat (Chronic Oral)
3.01
Fathead Minnow
4.88
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
391.69
Hydration Free Energy
-9.36
Log(D) at pH=7.4
3.87
Log(P)
5.64
Log S
-5.12
Log(Vapor Pressure)
-8.11
Melting Point
110.45
pKa Acid
9.59
pKa Basic
7.48
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.9464
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.9441
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9275
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8869
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8818
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8790
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8738
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8697
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8695
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8639
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8618
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8559
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8483
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8461
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8449
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8419
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8322
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8293
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8218
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8183
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8129
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8125
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8115
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.8101
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8090
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8038
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8007
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8002
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7981
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7966
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7931
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7923
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7902
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7901
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7892
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7885
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7857
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7852
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7846
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7824
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7819
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7798
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7796
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7793
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7778
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7773
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 4 0.7766
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7763
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7733
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7685
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7669
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7668
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7668
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7666
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 2 0.7647
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7640
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 3 0.7614
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7605
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7598
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7598
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7596
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7590
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7579
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7577
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7573
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7573
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7544
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 2 0.7537
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7532
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7527
Cytochrome P450 3A4 P08684 CP3A4_HUMAN Homo sapiens 3 0.7521
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7520
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7517
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7514
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7512
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7500
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7494
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7477
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7473
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7454
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7452
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7449
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7411
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7411
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7405
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7390
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7384
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7380
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7343
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7338
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7337
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7336
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7309
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7299
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7298
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7289
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7268
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7263
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7253
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7244
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7241
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7225
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7225
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7214
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7211
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7204
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7203
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7192
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7182
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7175
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7175
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7162
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7158
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7158
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7155
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7155
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7146
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7144
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7135
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7129
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7118
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7113
CRP-like cAMP-activated global transcriptional regulator P9WMH3 CRPL_MYCTU Mycobacterium tuberculosis 3 0.7109
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7108
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7107
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7100
Adenosine 5'-monophosphoramidase HINT1 P49773 HINT1_HUMAN Homo sapiens 3 0.7094
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7087
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7082
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7077
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7072
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7072
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7070
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7069
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7056
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7054
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7051
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7043
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7028
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7019
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7017
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 2 0.7010

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