Torosachrysone - Compound Card

Torosachrysone

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Torosachrysone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1cc2cc3CC(C)(O)CC(=O)c3c(c2c(c1)O)O
InChI InChI=1S/C16H16O5/c1-16(20)6-9-3-8-4-10(21-2)5-11(17)13(8)15(19)14(9)12(18)7-16/h3-5,17,19-20H,6-7H2,1-2H3
InChIKey BFMIUBHJKFRWIV-UHFFFAOYSA-N
Formula C16H16O5
HBA 5
HBD 3
MW 288.3
Rotatable Bonds 1
TPSA 86.99
LogP 2.14
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.31
Exact Mass 288.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Senna multiglandulosa Leguminosae/Fabaceae Plantae 1574110
2 Senna floribunda Leguminosae/Fabaceae Plantae 2601732
3 Senna septemtrionalis Leguminosae/Fabaceae Plantae 346998
4 Senna Didymobotrya Leguminosae/Fabaceae Plantae 72401

Showing of synonyms

  • Alemayehu G, Woldeyesus B, et al. (1997). (+)-Floribundone 3 from the pods of Senna septemtrionalis.. Bulletin of the Chemical Society of Ethiopia,1997,11(1),25-30. [View] [PubMed]
  • Alemayehu G, Abegaz BM. (1996). Bianthraquinones from the seeds of Senna multiglandulosa. Phytochemistry,1996,41(3),919-921. [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]
  • 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]
Pubchem: 10446798
Nmrshiftdb2: 60063975

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 288.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.66
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
-1.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.810
Plasma Protein Binding
47.98
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
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.960
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.080
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.460
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.370
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
3.730
Rat (Acute)
2.320
Rat (Chronic Oral)
2.900
Fathead Minnow
4.160
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
411.540
Hydration Free Energy
-11.130
Log(D) at pH=7.4
2.260
Log(P)
2.86
Log S
-4.16
Log(Vapor Pressure)
-6.58
Melting Point
179.06
pKa Acid
7.24
pKa Basic
4.98
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9611
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9611
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9171
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9171
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9100
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9100
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8920
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8920
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8911
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8911
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8878
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8878
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8860
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8860
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8860
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8860
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8795
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8795
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8726
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8726
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8688
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8688
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8683
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8683
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8661
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8661
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8470
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8470
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8468
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8468
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8452
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8452
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8418
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8418
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8342
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8342
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8338
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8338
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8324
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8324
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8322
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8322
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8310
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8310
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8206
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8206
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8204
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8204
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8181
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8181
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8178
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8178
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8144
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8144
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8106
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8106
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8048
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8048
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8025
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8025
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8004
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8004
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7903
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7903
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7901
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7901
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7758
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7758
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7753
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7753
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7744
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7744
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7743
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7743
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7670
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7670
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7628
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7628
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7585
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7585
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7578
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7578
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7538
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7538
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7537
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7537
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7534
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7534
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7524
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7524
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7518
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7518
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7465
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7465
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7446
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7446
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7424
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7424
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7389
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7389
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7385
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7385
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7384
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7384
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7366
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7366
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7309
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7309
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7261
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7261
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7204
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7204
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7191
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7191
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7180
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7180
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7166
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7166
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7165
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7165
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7158
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7158
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7141
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7141
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.7107
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.7107
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7098
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7098
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7098
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7098
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 4 0.7094
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 4 0.7094
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7082
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7082
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7064
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7064
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7062
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7062
Tyrosine-protein kinase ABL1 P00519 ABL1_HUMAN Homo sapiens 3 0.7061
Tyrosine-protein kinase ABL1 P00519 ABL1_HUMAN Homo sapiens 3 0.7061
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7055
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7055
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7053
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7053
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7038
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7038
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7027
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7027
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7006
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7006

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