3-geranyloxyemodine - Compound Card

3-geranyloxyemodine

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3-geranyloxyemodine

Structure
Zoomed Structure
  • Family: Hypericaceae, Clusiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles C/C(=C\COc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)C)/CC=C(C)C
InChI InChI=1S/C24H24O5/c1-13(2)5-6-14(3)7-8-29-16-11-18-22(20(26)12-16)24(28)21-17(23(18)27)9-15(4)10-19(21)25/h5,7,9-12,25-26H,6,8H2,1-4H3/b14-7+
InChIKey JWWMVDHSTSULKQ-VGOFMYFVSA-N
Formula C24H24O5
HBA 5
HBD 2
MW 392.45
Rotatable Bonds 5
TPSA 83.83
LogP 4.86
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 392.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Vismia laurentii Clusiaceae Plantae 2704497
2 Psorospermum densipunctatum Hypericaceae Plantae 999533

Showing of synonyms

  • 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]
  • Sass G, Tsamo AT, et al. (2019). Vismione B Interferes with Trypanosoma cruzi Infection of Vero Cells and Human Stem Cell-Derived Cardiomyocytes.. The American journal of tropical medicine and hygiene,2019, 101(6), 1359-1368. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 208.22 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.16
Plasma Protein Binding
69.54
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.34
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.16
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.93
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.03
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
-6.47
Rat (Acute)
2.28
Rat (Chronic Oral)
2.79
Fathead Minnow
5.48
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
478.54
Hydration Free Energy
-6.94
Log(D) at pH=7.4
4.13
Log(P)
6.86
Log S
-7.44
Log(Vapor Pressure)
-8.71
Melting Point
172.01
pKa Acid
7.73
pKa Basic
5.37
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 0.9610
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9338
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9167
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9015
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8929
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8862
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8862
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8748
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8700
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8646
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8638
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8631
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8582
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8483
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8429
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8419
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8399
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8315
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8294
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8289
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8276
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8234
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8187
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8180
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.8153
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8111
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.8108
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.8035
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8031
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7994
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7952
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7937
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7934
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7907
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7875
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7873
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7843
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7807
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7761
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7750
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7727
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7726
Cytochrome b6 P83791 CYB6_MASLA Mastigocladus laminosus 3 0.7725
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7712
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7684
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7682
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7677
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7665
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7643
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7614
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7613
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 2 0.7604
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7603
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7596
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7593
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7592
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7585
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7585
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7578
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7567
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7565
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7551
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7526
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7520
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7519
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7505
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7502
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7495
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7493
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7484
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7466
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7466
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7440
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7438
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7432
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7425
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7420
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7419
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7419
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7418
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7416
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7416
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7412
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7408
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7405
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7400
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7398
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7390
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7387
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7387
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7378
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7372
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7358
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7346
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7342
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7339
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7326
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7320
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7318
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7315
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7304
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7296
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7292
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7289
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7286
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7277
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7260
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7260
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7259
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7249
Bifunctional F420 biosynthesis protein FbiB P9WP79 FBIB_MYCTU Mycobacterium tuberculosis 5 0.7248
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7237
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7235
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7228
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7222
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7209
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7202
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7192
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7191
Orotidine 5'-phosphate decarboxylase Q9KQT7 PYRF_VIBCH Vibrio cholerae serotype O1 4 0.7180
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7175
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7171
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7156
Reaction center protein L chain P0C0Y8 RCEL_RHOSH Rhodobacter sphaeroides 3 0.7152
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7151
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7149
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7145
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7144
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7142
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7140
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7137
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7128
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 3 0.7126
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7126
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 4 0.7119
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.7107
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 2 0.7103
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7100
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7097
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 3 0.7068
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7062
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7056
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7055
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7048
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7042
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7040
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7033
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7028
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7027
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7026
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 4 0.7026
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7022
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 4 0.7016
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7015
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7011
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7008
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7006
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7005
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7001

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