Isoxanthorin - Compound Card

Isoxanthorin

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Isoxanthorin

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1cc(O)c2c(c1O)C(=O)c1c(C2=O)cc(cc1O)C
InChI InChI=1S/C16H12O6/c1-6-3-7-11(8(17)4-6)16(21)13-12(14(7)19)9(18)5-10(22-2)15(13)20/h3-5,17-18,20H,1-2H3
InChIKey AMASMQWBGMKOFH-UHFFFAOYSA-N
Formula C16H12O6
HBA 6
HBD 3
MW 300.27
Rotatable Bonds 1
TPSA 104.06
LogP 1.9
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 300.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aloe secundiflora Asphodelaceae Plantae 1593107
2 Aloe saponaria Asphodelaceae Plantae 1155789

Showing of synonyms

  • Induli M, Cheloti M, et al. (2012). Naphthoquinones from the roots of Aloe secundiflora. Phytochemistry Letters,2012,5(3),506-509. [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: 85926407
Nmrshiftdb2: 60076363

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 300.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.880
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.8

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.930
Plasma Protein Binding
68.82
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.810
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.120
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.980
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.560
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
4.280
Rat (Acute)
2.520
Rat (Chronic Oral)
3.450
Fathead Minnow
4.250
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
432.090
Hydration Free Energy
-8.090
Log(D) at pH=7.4
2.720
Log(P)
3.72
Log S
-6.51
Log(Vapor Pressure)
-6.91
Melting Point
220.82
pKa Acid
7.3
pKa Basic
3.73
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9501
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9501
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9483
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9483
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9280
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9280
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9104
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9104
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9092
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9092
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9058
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9058
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8970
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8970
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8892
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8892
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8878
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8878
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8802
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8802
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8776
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8776
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8681
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8681
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8601
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8601
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8588
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8588
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8518
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8518
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8326
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8326
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8307
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8307
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8295
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8295
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8261
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8261
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8209
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8209
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 4 0.8184
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 4 0.8184
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8149
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8149
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8117
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8117
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8085
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8085
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8081
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8081
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8002
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8002
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7991
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7991
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7946
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7946
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7885
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7885
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7885
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7885
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7833
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7833
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7824
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7824
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7812
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7812
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7801
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7801
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7787
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7787
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7726
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7726
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7718
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7718
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7716
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7716
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7693
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7693
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7684
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7684
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7672
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7672
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 4 0.7665
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 4 0.7665
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7660
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7660
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7640
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7640
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7622
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7622
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7621
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7621
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7611
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7611
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 5 0.7523
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 5 0.7523
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7496
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7496
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7485
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7485
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7484
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7484
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7472
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7472
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7461
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7461
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7455
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7455
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7449
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7449
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7428
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7428
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7420
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7420
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7385
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7385
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7377
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7377
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7366
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7366
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7329
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7329
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.7323
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.7323
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7286
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7286
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7234
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7234
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7224
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7224
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7199
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7199
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7199
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7199
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7155
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7155
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7152
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7152
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7144
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7144
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7138
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7138
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7129
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7129
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7113
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7113
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7102
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7102
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7096
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7096
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7090
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7090
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7081
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7081
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7081
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7081
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7073
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7073
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7056
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7056
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7028
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7028
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7027
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7027
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7005
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7005
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7001
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7001

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