Emodinanthrone-6-O-rhamnopyranoside-2',3'4'-triacetate - Compound Card

Emodinanthrone-6-O-rhamnopyranoside-2',3'4'-triacetate

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Emodinanthrone-6-O-rhamnopyranoside-2',3'4'-triacetate

Structure
Zoomed Structure
  • Family: Rhamnaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles CC(=O)O[C@@H]1C(Oc2cc(O)c3c(c2)Cc2c(C3=O)c(O)cc(c2)C)O[C@@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)C
InChI InChI=1S/C27H28O11/c1-11-6-16-8-17-9-18(10-20(32)22(17)23(33)21(16)19(31)7-11)38-27-26(37-15(5)30)25(36-14(4)29)24(12(2)34-27)35-13(3)28/h6-7,9-10,12,24-27,31-32H,8H2,1-5H3/t12-,24-,25+,26+,27?/m1/s1
InChIKey ZOYPBNGHEPSADD-LVNABKJTSA-N
Formula C27H28O11
HBA 11
HBD 2
MW 528.51
Rotatable Bonds 5
TPSA 154.89
LogP 2.46
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.41
Exact Mass 528.16
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Rhamnus prinoides Rhamnaceae Plantae 280022

Showing of synonyms

  • Abegaz BM, Peter MG. (1995). Emodin and emodinanthrone rhamnoside acetates from fruits of Rhamnus prinoides. Phytochemistry,1995,39(6),1411-1414. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(C2=O)c1Cc(c23)cc(cc3)OC4CCCCO4

Level: 1

Mol. Weight: 294.35 g/mol

Structure

SMILES: c1cccc(c12)Cc3c(C2=O)cccc3

Level: 0

Mol. Weight: 194.23 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.35
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.42

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.8
Plasma Protein Binding
79.29
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.76
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.4
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.95
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.43
Micronucleos
Toxic
NR-AhR
Safe
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
-780.74
Rat (Acute)
2.6
Rat (Chronic Oral)
2.65
Fathead Minnow
6.24
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
502.54
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.62
Log(P)
4.6
Log S
-4.34
Log(Vapor Pressure)
-9.65
Melting Point
183.67
pKa Acid
7.63
pKa Basic
1.59
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.9152
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.9152
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9019
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9019
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8926
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8926
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8723
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8723
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8660
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8660
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8589
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8589
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8543
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8543
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8367
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8367
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8365
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8365
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.8323
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.8323
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8111
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8111
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7997
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7997
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7992
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7992
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7933
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7933
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7901
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7901
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7884
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7884
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7851
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7851
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7834
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7834
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7833
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7833
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7823
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7823
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7804
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7804
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7799
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7799
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7731
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7731
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7627
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7627
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7617
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7617
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7541
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7541
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7535
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7535
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7492
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7492
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7461
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7461
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7453
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7453
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7447
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7447
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7417
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7417
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7416
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7416
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7412
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7412
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7389
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7389
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7382
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7382
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7358
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7358
Enoyl-acyl carrier reductase Q6UCJ9 Q6UCJ9_TOXGO Toxoplasma gondii 4 0.7339
Enoyl-acyl carrier reductase Q6UCJ9 Q6UCJ9_TOXGO Toxoplasma gondii 4 0.7339
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.7335
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.7335
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7324
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7324
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7316
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7316
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7314
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7314
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7299
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7299
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7293
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7293
Death-associated protein kinase 3 O43293 DAPK3_HUMAN Homo sapiens 2 0.7288
Death-associated protein kinase 3 O43293 DAPK3_HUMAN Homo sapiens 2 0.7288
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7285
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7285
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7279
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7279
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7231
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7231
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7208
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7208
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7197
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7197
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7194
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7194
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7176
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7176
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7172
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7172
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7167
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7167
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7151
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7151
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7149
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7149
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7144
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7144
Thymidine phosphorylase P07650 TYPH_ECOLI Escherichia coli 4 0.7100
Thymidine phosphorylase P07650 TYPH_ECOLI Escherichia coli 4 0.7100
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7064
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 4 0.7064
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7064
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 4 0.7064
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7038
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7038
Reductase homolog Q9ZGC1 Q9ZGC1_STRCY Streptomyces cyanogenus 4 0.7036
Reductase homolog Q9ZGC1 Q9ZGC1_STRCY Streptomyces cyanogenus 4 0.7036
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7000
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7000

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