Leptosphaerin D - Compound Card

Leptosphaerin D

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Leptosphaerin D

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
Canonical Smiles Oc1c(C)cc(c2c1COc1c(C2=O)c(O)ccc1)O
InChI InChI=1S/C15H12O5/c1-7-5-10(17)12-8(14(7)18)6-20-11-4-2-3-9(16)13(11)15(12)19/h2-5,16-18H,6H2,1H3
InChIKey LLVQPFGOXOWCAA-UHFFFAOYSA-N
Formula C15H12O5
HBA 5
HBD 3
MW 272.26
Rotatable Bonds 0
TPSA 86.99
LogP 2.24
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 272.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Bulbine frutescens Asphodelaceae Plantae 210954

Showing of synonyms

  • Abdissa N, Heydenreich M, et al. (2014). A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones. Phytochemistry Letters,2014,9,67-73. [View] [PubMed]
Pubchem: 46831109
Nmrshiftdb2: 80007861

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)COc3c(C2=O)cccc3

Level: 0

Mol. Weight: 272.26 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.920
Plasma Protein Binding
65.41
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.430
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.980
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.230
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.760
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
4.480
Rat (Acute)
2.440
Rat (Chronic Oral)
3.050
Fathead Minnow
4.250
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
409.030
Hydration Free Energy
-9.270
Log(D) at pH=7.4
2.760
Log(P)
3.42
Log S
-4.62
Log(Vapor Pressure)
-7.33
Melting Point
191.26
pKa Acid
6.15
pKa Basic
5.79
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.9220
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.9220
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9172
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9172
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.9085
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.9085
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9081
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9081
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.8963
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.8963
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8797
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8797
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.8696
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.8696
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8497
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8497
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8488
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8488
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8409
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8409
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8398
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8398
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8395
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8395
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8352
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8352
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8349
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8349
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8337
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8337
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8281
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8281
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8233
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8233
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8202
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8202
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8190
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8190
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8135
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8135
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8130
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8130
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8125
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8125
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8092
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8092
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 4 0.8069
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 4 0.8069
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8059
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8059
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8058
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8058
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.8022
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.8022
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8003
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8003
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7965
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7965
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7899
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7899
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7865
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7865
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7862
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7862
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7860
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7860
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7847
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7847
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7802
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7802
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7740
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7740
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.7723
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.7723
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7716
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7716
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7713
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7713
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7704
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7704
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7682
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7682
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7671
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7671
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7659
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7659
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7646
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7646
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7617
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7617
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7602
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7602
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7570
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7570
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7566
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7566
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7522
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7522
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7502
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7502
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7499
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7499
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7487
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7487
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7444
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7444
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7443
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7443
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7437
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7437
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7420
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7420
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7417
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7417
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.7408
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.7408
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7387
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7387
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7383
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7383
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7365
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7365
Enoyl-acyl carrier protein reductase Q6TEI5 Q6TEI5_PLABE Plasmodium berghei 4 0.7365
Enoyl-acyl carrier protein reductase Q6TEI5 Q6TEI5_PLABE Plasmodium berghei 4 0.7365
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7359
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7359
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7357
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7357
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7348
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7348
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7308
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7308
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7299
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7299
Transketolase 1 P23254 TKT1_YEAST Saccharomyces cerevisiae 4 0.7212
Transketolase 1 P23254 TKT1_YEAST Saccharomyces cerevisiae 4 0.7212
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7192
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7192
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7163
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7163
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7156
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7156
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7154
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7154
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7147
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7147
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7141
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7141
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7136
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7136
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7125
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7125
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7104
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7104
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7092
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7092
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7089
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7089
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7063
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7063
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7057
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7057
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 4 0.7046
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7046
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 4 0.7046
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7046
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7038
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7038
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7037
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7037
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7035
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7035
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7029
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7029
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7020
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7020

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