2,4-dihydroxy-3,5-bis(3-methylbut-2-enyl)-6-pentylbenzoic acid - Compound Card

2,4-dihydroxy-3,5-bis(3-methylbut-2-enyl)-6-pentylbenzoic acid

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2,4-dihydroxy-3,5-bis(3-methylbut-2-enyl)-6-pentylbenzoic acid

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles CCCCCc1c(CC=C(C)C)c(O)c(c(c1C(=O)O)O)CC=C(C)C
InChI InChI=1S/C22H32O4/c1-6-7-8-9-16-17(12-10-14(2)3)20(23)18(13-11-15(4)5)21(24)19(16)22(25)26/h10-11,23-24H,6-9,12-13H2,1-5H3,(H,25,26)
InChIKey NWABSQLHKJWTBK-UHFFFAOYSA-N
Formula C22H32O4
HBA 3
HBD 3
MW 360.49
Rotatable Bonds 9
TPSA 77.76
LogP 5.55
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 360.23
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: 45783218

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 360.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.47
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.93
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.39
Plasma Protein Binding
67.78
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
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
Non-Inhibitor

Excretion

Clearance
2.98
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.18
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.36
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.86
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
3.58
Rat (Acute)
2.29
Rat (Chronic Oral)
2.54
Fathead Minnow
4.27
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
387.63
Hydration Free Energy
-7.01
Log(D) at pH=7.4
2.28
Log(P)
7.99
Log S
-4.45
Log(Vapor Pressure)
-9.47
Melting Point
160.24
pKa Acid
5.47
pKa Basic
7.35
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8849
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8523
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8503
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.8272
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8256
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8083
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8043
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7994
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7979
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7977
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7936
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7910
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7821
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7766
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7744
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7700
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7477
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7459
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7381
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7339
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7252
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7223
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7204
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7177
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7147
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7112
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7068
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7066
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7063
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7056
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7049
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7040
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7033
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7030
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7024

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