2-isoprenyl-3-methoxyemodine - Compound Card

2-isoprenyl-3-methoxyemodine

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2-isoprenyl-3-methoxyemodine

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1cc2c(c(c1/C=C/C(C)C)O)C(=O)c1c(C2=O)cc(cc1O)C
InChI InChI=1S/C21H20O5/c1-10(2)5-6-12-16(26-4)9-14-18(20(12)24)21(25)17-13(19(14)23)7-11(3)8-15(17)22/h5-10,22,24H,1-4H3/b6-5+
InChIKey FMUNWYQUOSZHBF-AATRIKPKSA-N
Formula C21H20O5
HBA 5
HBD 2
MW 352.39
Rotatable Bonds 3
TPSA 83.83
LogP 3.86
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 352.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Vismia laurentii Clusiaceae Plantae 2704497
2 Vismia guineensis Guttiferae Plantae 999599
3 Harungana madagascariensis Hypericaceae Plantae 198768
4 Psorospermum aurantiacum Hypericaceae Plantae 999533
5 Psorospermum densipunctatum Hypericaceae Plantae 999533

Showing of synonyms

  • Kouam SF, Khan SN, et al. (2006). Alpha-glucosidase inhibitory anthranols, kenganthranols A-C, from the stem bark of Harungana madagascariensis.. Journal of natural products,2006, 69(2), 229-233. [View] [PubMed]
  • Tala M, Talontsi F, et al. (2013). Anthraquinones and triterpenoids from seeds of Vismia guineensis. Biochemical Systematics and Ecology, 2013, 50, 310-312. [View]
  • Kemegne GA, Mkounga P, et al. (2017). Antimicrobial structure activity relationship of five anthraquinones of emodine type isolated from Vismia laurentii.. BMC microbiology,2017, 17(1), 41. [View] [PubMed]
  • Tanemossu S, Franke K, et al. (2015). Chemical constituents of Psorospermum densipunctatum (Hypericaceae). Biochemical Systematics and Ecology, 2015, 59, 174-176. [View]
  • Tiani G, Ahmed I, et al. (2013). Kenganthranol F, a new Anthranol from Psorospermum aurantiacum.. Natural Product Communications, 2013, 8(1), 103-104. [View] [PubMed]
Pubchem: 5378723
Nmrshiftdb2: 60025854

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 352.39 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.57
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.640
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.160
Plasma Protein Binding
73.11
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
6.800
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.470
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.780
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.080
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
2.810
Rat (Acute)
2.280
Rat (Chronic Oral)
3.320
Fathead Minnow
5.110
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
447.020
Hydration Free Energy
-9.160
Log(D) at pH=7.4
3.820
Log(P)
5.76
Log S
-7.26
Log(Vapor Pressure)
-7.67
Melting Point
179.44
pKa Acid
6.9
pKa Basic
4.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9347
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9161
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8929
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8754
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8725
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8590
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8562
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8507
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8407
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8399
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8287
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8265
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8189
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7888
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7723
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7707
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7692
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7674
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7673
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7671
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7640
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7628
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7626
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7607
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7602
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7574
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7545
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7541
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7540
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7490
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7490
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7435
Orotidine 5'-phosphate decarboxylase Q9KQT7 PYRF_VIBCH Vibrio cholerae serotype O1 4 0.7386
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7378
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7339
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7333
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7329
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7323
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7310
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7240
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7187
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 3 0.7156
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7143
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7141
Bifunctional F420 biosynthesis protein FbiB P9WP79 FBIB_MYCTU Mycobacterium tuberculosis 5 0.7080
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7078
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7073
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7072
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7040
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7035

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