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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles CCCCCc1c(C(=O)O)c(O)c(c(c1CC=C(C)C)OC)CC=C(C)C
InChI InChI=1S/C23H34O4/c1-7-8-9-10-17-18(13-11-15(2)3)22(27-6)19(14-12-16(4)5)21(24)20(17)23(25)26/h11-12,24H,7-10,13-14H2,1-6H3,(H,25,26)
InChIKey ONMLNUSSUHTGJO-UHFFFAOYSA-N
Formula C23H34O4
HBA 3
HBD 2
MW 374.52
Rotatable Bonds 10
TPSA 66.76
LogP 5.85
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 374.25
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: 45783217

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 374.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.33
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.88
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.76
Plasma Protein Binding
72.71
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
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.55
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.06
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.08
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
2.65
Rat (Acute)
2.15
Rat (Chronic Oral)
2.68
Fathead Minnow
4.39
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
376.11
Hydration Free Energy
-5.48
Log(D) at pH=7.4
2.5
Log(P)
8.36
Log S
-4.71
Log(Vapor Pressure)
-8.34
Melting Point
135.8
pKa Acid
5.47
pKa Basic
6.68
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8373
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8356
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8273
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7936
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7862
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7784
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7610
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.7592
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7589
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7582
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7491
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7474
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7443
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7426
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7386
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7349
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7304
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7301
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7285
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 3 0.7283
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7261
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7255
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7244
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7162
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 3 0.7133
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7118
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7085
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7083
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7066
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7060
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7054
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7051
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7040
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7038
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7016
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7008

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