Aloechrysone - Compound Card

Aloechrysone

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Aloechrysone

Structure
Zoomed Structure
  • Family: Plantae - Liliaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Pre-Anthraquinone
Canonical Smiles COc1cccc2c1c(O)c1c(c2)C[C@@](CC1=O)(C)O
InChI InChI=1S/C16H16O4/c1-16(19)7-10-6-9-4-3-5-12(20-2)14(9)15(18)13(10)11(17)8-16/h3-6,18-19H,7-8H2,1-2H3/t16-/m1/s1
InChIKey LVSOUEJUPADCBE-MRXNPFEDSA-N
Formula C16H16O4
HBA 4
HBD 2
MW 272.3
Rotatable Bonds 1
TPSA 66.76
LogP 2.43
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.31
Exact Mass 272.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aloe berhana Asphodelaceae Plantae 1593069
2 Aloe berhana Asphodelaceae Plantae 1593069
3 Aloe rivae Asphodelaceae Plantae 1811902
4 Aloe megalacantha Asphodelaceae Plantae 1389516
5 Aloe behana Asphodelaceae Plantae 25641
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]
  • 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]
  • 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: 101712954
Nmrshiftdb2: 60076327

No compound-protein relationship available.

Structure

SMILES: O=C1CCCc(c12)cc3c(c2)cccc3

Level: 0

Mol. Weight: 272.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.57
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.680
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.920
Plasma Protein Binding
69.78
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.150
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.370
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.010
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.250
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
1.950
Rat (Acute)
2.500
Rat (Chronic Oral)
2.350
Fathead Minnow
4.180
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
394.440
Hydration Free Energy
-10.730
Log(D) at pH=7.4
2.640
Log(P)
3.14
Log S
-3.54
Log(Vapor Pressure)
-6.72
Melting Point
160.89
pKa Acid
7.2
pKa Basic
5.41
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9454
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9454
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9399
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9399
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9288
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9288
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9275
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9275
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9178
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9178
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9121
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9121
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9069
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9069
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9064
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9064
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9059
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9059
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.8942
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.8942
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8921
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8921
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8906
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8906
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8824
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8824
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8722
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8722
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8707
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8707
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8691
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8691
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.8684
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.8684
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8613
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8613
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8553
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8553
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8493
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8493
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8487
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8487
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8433
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8433
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8194
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8194
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8180
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8180
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8060
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8060
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7983
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7983
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7964
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7964
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7955
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7955
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7901
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7901
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7885
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7885
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7853
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7853
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7844
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7844
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7809
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7809
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7727
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7727
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7727
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7727
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7597
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7597
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7594
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7594
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7577
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7577
Protein mono-ADP-ribosyltransferase PARP14 Q460N5 PAR14_HUMAN Homo sapiens 3 0.7570
Protein mono-ADP-ribosyltransferase PARP14 Q460N5 PAR14_HUMAN Homo sapiens 3 0.7570
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7564
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7564
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7473
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7473
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7428
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7428
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7392
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7392
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7385
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7385
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7325
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7325
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7316
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7316
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7310
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7310
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 3 0.7291
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 3 0.7291
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7277
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7277
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7266
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7266
Protein mono-ADP-ribosyltransferase PARP10 Q53GL7 PAR10_HUMAN Homo sapiens 3 0.7265
Protein mono-ADP-ribosyltransferase PARP10 Q53GL7 PAR10_HUMAN Homo sapiens 3 0.7265
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7264
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7264
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7252
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7252
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 3 0.7243
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 3 0.7243
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7232
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7232
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7228
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7228
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7223
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7223
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7220
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7220
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7219
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7219
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7214
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7214
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7198
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7198
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7197
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7197
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7183
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7183
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7174
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7174
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7129
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7129
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7116
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7116
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7077
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7077
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7064
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7064
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7061
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7061
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7042
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7042
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7015
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7015
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7011
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7011
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7005
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7005

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