Aloe emodin - Compound Card

Aloe emodin

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Aloe emodin

Structure
Zoomed Structure
  • Family: Plantae - Commelinaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles OCc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)ccc1
InChI InChI=1S/C15H10O5/c16-6-7-4-9-13(11(18)5-7)15(20)12-8(14(9)19)2-1-3-10(12)17/h1-5,16-18H,6H2
InChIKey YDQWDHRMZQUTBA-UHFFFAOYSA-N
Formula C15H10O5
HBA 5
HBD 3
MW 270.24
Rotatable Bonds 1
TPSA 94.83
LogP 1.37
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 270.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia polyacantha Euphorbiaceae Plantae 260993
2 Aloe sinkatana Asphodelaceae Plantae 210945
3 Aloe sinkatana Asphodelaceae Plantae 210945
4 Kniphofia foliosa Asphodelaceae Plantae 214838
5 Aloe berhana Asphodelaceae Plantae 1593069
6 Aloe rivae Asphodelaceae Plantae 1811902
7 Aloe megalacantha Asphodelaceae Plantae 1389516
8 Aloe species Asphodelaceae Plantae 117795
9 Senna floribunda Leguminosae/Fabaceae Plantae 2601732
10 Senna Didymobotrya Leguminosae/Fabaceae Plantae 72401
11 Rumex abysinicus Polygonaceae Plantae 273505
12 Kniphofia species Liliaceae Plantae 49723
13 Callisia fragrans Commelinaceae Plantae 428217

Showing of synonyms

  • Berhanu E, Fetene M, et al. (1986). Anthraquinones as taxonomic markers in Ethiopian Kniphofia species.. Phytochemistry,1986,25(4),847-850. [View] [PubMed]
  • Induli M, Gebru M, et al. (2013). Antiplasmodial Quinones from the Rhizomes of Kniphofia foliosa. Natural Product Communications,2013,8(9),1261-1264. [View] [PubMed]
  • ELhassan GOM, Adhikari A, et al. (2015). Chemical constituents of Euphorbia Polyacantha Boiss. and their immunomodulatory properties. Records of Natural Products,2015,9(1),146-152. [View]
  • El Sohafy S.M, Nassra R.A, et al. (2021). Chemical profiling and biological screening with potential anti-inflammatory activity of Callisia fragrans grown in Egypt. Natural product research, 2021, 35(23), 5521-5524. [View] [PubMed]
  • Dagne E, Alemu M. (1991). Constituents of the leaves of four Aloe species from Ethiopia. Bulletin of the Chemical Society of Ethiopia,1991,5(2),87-91. [View] [PubMed]
  • ELhassan GOM, Adhikari A, et al. (2011). Phytochemical and biological studies on Aloe sinkatana Berger. The 14th NAPRECA Symposium and AAMPS Ethnoveterinary Medicine Symposium, At Nairobi, Kenya. August 2011. [View]
  • Bizuayehu Z, Ashebir F. (2012). Phytochemical investigation on the root of Rumex abyssinicus (Makmako). M.Sc. Thesis, Addis Ababa University, Ethiopia,2012. [View] [PubMed]
  • Tsegaye G, Alemayehu G. (2006). Phytochemical investigation on the stem bark of Senna floribunda. M.Sc. Thesis, Addis Ababa University, Ethiopia,2006. [View] [PubMed]
  • ELhassan GOM, Adhikari A, et al. (2012). Phytochemistry and antiglycation activity of Aloe sinkatana Reynolds. Phytochemistry Letters,2012,5(4),725-728. [View]
  • Alemayehu G, Abegaz B, et al. (1989). Quinones of Senna Didymobotrya.. Bulletin of the Chemical Society of Ethiopia,1989,3(1),37-40. [View] [PubMed]
  • Dagne E. (1996). Review of the chemistry of Aloes of Africa. Bulletin of the Chemical Society of Ethiopia,1996,10(1),89-103. [View] [PubMed]
Pubchem: 10207
Kegg Ligand: C10294
Chebi: 2607
Nmrshiftdb2: 2493
Metabolights: MTBLC2607
Bindingdb: 50085551
CPRiL: 55238
Structure

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

Level: 0

Mol. Weight: 270.24 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.71
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.76
Plasma Protein Binding
58.72
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.29
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.83
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.99
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.83
Micronucleos
Toxic
NR-AhR
Toxic
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
3.85
Rat (Acute)
2.45
Rat (Chronic Oral)
3.4
Fathead Minnow
4.1
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
432.72
Hydration Free Energy
-11.88
Log(D) at pH=7.4
1.47
Log(P)
2.78
Log S
-4.72
Log(Vapor Pressure)
-8.21
Melting Point
202.16
pKa Acid
6.16
pKa Basic
5.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9450
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9450
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9383
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9383
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9348
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9348
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8853
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8853
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8741
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8741
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8542
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8542
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8535
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8535
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8453
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8453
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8378
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8378
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8318
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8318
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8315
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8315
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8309
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8309
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8294
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8294
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8141
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8141
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8101
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8101
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8027
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8027
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7993
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7993
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7978
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7978
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7946
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7946
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7934
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7934
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7906
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7906
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7898
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7898
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7834
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7834
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7794
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7794
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7771
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7771
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7670
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7670
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7663
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7663
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7641
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7641
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7595
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7595
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7534
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7534
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7503
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7503
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7477
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7477
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7430
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7430
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7428
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7428
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7422
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7422
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7406
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7406
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.7383
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.7383
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7378
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7378
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7367
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7367
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7349
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7349
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7303
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7303
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7299
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7299
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7245
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7245
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7242
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7242
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7233
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7233
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7231
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7231
Aklanonic acid methyl ester cyclase AcmA O52646 DNRD_STRGJ Streptomyces galilaeus 3 0.7213
Aklanonic acid methyl ester cyclase AcmA O52646 DNRD_STRGJ Streptomyces galilaeus 3 0.7213
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7208
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7208
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7206
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7206
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7198
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7198
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7194
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7194
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7193
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7193
Nicotinamide riboside kinase 1 Q9NWW6 NRK1_HUMAN Homo sapiens 4 0.7187
Nicotinamide riboside kinase 1 Q9NWW6 NRK1_HUMAN Homo sapiens 4 0.7187
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7181
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7181
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7146
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7146
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7126
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7126
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7108
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7108
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7069
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7069
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7054
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7054
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7045
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7045
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7034
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7034
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7033
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7033
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7033
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7033
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7031
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7031
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7028
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7028
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7022
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7022
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7021
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7021

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