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

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

Select a section from the left sidebar

2,4-bis(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
InChI InChI=1S/C21H32O2/c1-6-7-8-9-17-14-20(22)19(13-11-16(4)5)21(23)18(17)12-10-15(2)3/h10-11,14,22-23H,6-9,12-13H2,1-5H3
InChIKey ZVLQJRXSGVAHOI-UHFFFAOYSA-N
Formula C21H32O2
HBA 2
HBD 2
MW 316.49
Rotatable Bonds 8
TPSA 40.46
LogP 5.85
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 316.24
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: 45783215
Chebi: 182686

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 316.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.48
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.63
Plasma Protein Binding
43.22
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.8
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.46
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.82
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.43
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
4.63
Rat (Acute)
1.81
Rat (Chronic Oral)
2.42
Fathead Minnow
4.77
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
358.57
Hydration Free Energy
-6.73
Log(D) at pH=7.4
4.58
Log(P)
7.34
Log S
-5.43
Log(Vapor Pressure)
-6.12
Melting Point
74.34
pKa Acid
11.19
pKa Basic
7.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8940
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8915
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8629
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8564
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8483
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8482
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8363
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8284
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8206
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8039
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8011
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7972
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7913
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7877
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7731
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7716
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7694
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7647
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7640
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7569
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7544
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7544
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7505
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7498
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7495
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7485
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7462
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7445
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7441
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7433
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7408
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7400
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7383
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7356
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7340
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7339
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7320
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7309
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7249
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7234
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7227
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7206
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7202
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7131
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7040
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7028
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7026
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7015
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 4 0.7009
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7001

Download SDF