Aloesaponarin I - Compound Card

Aloesaponarin I

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Aloesaponarin I

Structure
Zoomed Structure
  • Family: Plantae - Liliaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COC(=O)c1c(O)cc2c(c1C)C(=O)c1c(C2=O)cccc1O
InChI InChI=1S/C17H12O6/c1-7-12-9(6-11(19)13(7)17(22)23-2)15(20)8-4-3-5-10(18)14(8)16(12)21/h3-6,18-19H,1-2H3
InChIKey OWMIPWWYWUGBCG-UHFFFAOYSA-N
Formula C17H12O6
HBA 6
HBD 2
MW 312.28
Rotatable Bonds 1
TPSA 100.9
LogP 1.97
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 312.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aloe dawei Asphodelaceae Plantae 1331517
2 Aloe secundiflora Asphodelaceae Plantae 1593107
3 Aloe berhana Asphodelaceae Plantae 1593069
4 Aloe saponaria Asphodelaceae Plantae 1155789
5 Aloe pulcherrima Asphodelaceae Plantae 3161391
6 Aloe graminicola Liliaceae Plantae 330741
7 Aloe species Liliaceae Plantae 117795

Showing of synonyms

  • Yenesew A, Ogur JA, et al. (1993). (R)-Prechrysophanol from Aloe graminicola.. Phytochemistry,1993,34(5),1442-1444. [View] [PubMed]
  • Dagne E, Casser I, et al. (1992). Aloechrysone, a dihydroanthracenone from Aloe berhana.. Phytochemistry,1992,31(5),1791-1793. [View] [PubMed]
  • Dagne E, Yenesew A, et al. (1994). Anthraquinones, pre-anthraquinones and isoeleutherol in the roots of Aloe species.. Phytochemistry,1994,35(2),401-406. [View] [PubMed]
  • Abdissa N, Induli M, et al. (2014). Cytotoxic quinones from the roots of Aloe dawei. Molecules,2014,19(3),3264-3273. [View] [PubMed]
  • Induli M, Cheloti M, et al. (2012). Naphthoquinones from the roots of Aloe secundiflora. Phytochemistry Letters,2012,5(3),506-509. [View] [PubMed]
  • Abdissa D, Geleta G, et al. (2017). Phytochemical investigation of Aloe pulcherrima roots and evaluation for its antibacterial and antiplasmodial activities.. PLoS One,2017,12(3):e0173882. [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: 11098986
Nmrshiftdb2: 60080916

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 312.28 g/mol

Anti-plasmodial
Antibacterial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.630
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.870
Plasma Protein Binding
56.85
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
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
7.740
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.790
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.950
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.580
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
4.590
Rat (Acute)
2.600
Rat (Chronic Oral)
3.140
Fathead Minnow
4.430
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
437.220
Hydration Free Energy
-8.440
Log(D) at pH=7.4
3.010
Log(P)
4.24
Log S
-6.2
Log(Vapor Pressure)
-7.51
Melting Point
207.42
pKa Acid
7.93
pKa Basic
3.49
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 0.9467
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9467
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9305
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9305
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9191
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9191
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.9157
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.9157
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8950
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8950
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8947
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8947
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.8776
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.8776
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8664
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8664
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8657
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8657
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8519
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8519
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8477
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8477
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8393
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8393
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8392
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8392
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8346
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8346
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8332
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8332
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8325
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8325
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 3 0.8165
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 3 0.8165
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8063
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8063
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8010
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8010
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.7992
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.7992
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7819
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7819
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7815
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7815
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7807
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7807
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7805
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7805
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 4 0.7773
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 4 0.7773
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7726
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7726
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7701
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7701
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7693
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7693
L-malyl-CoA/beta-methylmalyl-CoA lyase Q3J5L6 MCAL_RHOS4 Cereibacter sphaeroides 3 0.7608
L-malyl-CoA/beta-methylmalyl-CoA lyase Q3J5L6 MCAL_RHOS4 Cereibacter sphaeroides 3 0.7608
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7601
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7601
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7601
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7601
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7584
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7584
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7560
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7560
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7557
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7557
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7528
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7528
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7497
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7497
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7469
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7469
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7469
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7469
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7454
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7454
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7444
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7444
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7428
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7428
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7422
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7422
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7339
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7339
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7324
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7324
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7319
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7319
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7303
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7303
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7299
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7299
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7282
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7282
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7244
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7244
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7219
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7219
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7208
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7208
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7201
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7201
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7196
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7196
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7163
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7163
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7153
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7153
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7149
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7149
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7130
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7130
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7075
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7075
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7067
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7067
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7059
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7059
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7035
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7035
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7027
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7027
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7025
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7025
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 3 0.7016
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 3 0.7016
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7013
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7013
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7005
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7005
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7004
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7004

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