Damnacanthol - Compound Card

Damnacanthol

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Damnacanthol

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1c2C(=O)c3ccccc3C(=O)c2cc(c1CO)O
InChI InChI=1S/C16H12O5/c1-21-16-11(7-17)12(18)6-10-13(16)15(20)9-5-3-2-4-8(9)14(10)19/h2-6,17-18H,7H2,1H3
InChIKey ASFZQCLAQPBWDN-UHFFFAOYSA-N
Formula C16H12O5
HBA 5
HBD 2
MW 284.27
Rotatable Bonds 2
TPSA 83.83
LogP 1.67
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 284.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pentas lanceolata Rubiaceae Plantae 25385
2 Pentas parvifolia Rubiaceae Plantae 296969
3 Pentas schimperi Rubiaceae Plantae 25384

Showing of synonyms

  • Goffin E, Ziemons E, et al. (2002). In vitro antiplasmodial activity of Tithonia diversifolia and identification of its main active constituent: tagitinin C.. Planta medica,2002, 68(6), 543-545. [View] [PubMed]
  • Bukuru J, De Kimpe N, et al. (2003). Isolation and structural elucidation of natural products from Pentas bussei K. Krause, Pentas lanceolata (Forsk.) Deflers and Pentas parvifolia Hiern (Rubiaceae). Ph.D. Thesis, University of Ghent, Faculty of Bioscience Engineering, Belgium,2003. [View] [PubMed]
  • Abdissa N, Pan F, et al. (2016). Naphthalene derivatives from the roots of Pentas parvifolia and Pentas bussei. Journal of Natural Products,2016,79(9),2181-2187. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 284.27 g/mol

Anti-15-lipoxygenase

Absorption

Caco-2 (logPapp)
-4.54
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.28
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
58.65
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-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
6.2
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.21
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.8
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.1
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
3.42
Rat (Acute)
2.37
Rat (Chronic Oral)
2.98
Fathead Minnow
4.35
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
409.45
Hydration Free Energy
-8.64
Log(D) at pH=7.4
0.79
Log(P)
2.38
Log S
-4.48
Log(Vapor Pressure)
-7.25
Melting Point
199.21
pKa Acid
7.47
pKa Basic
3.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9765
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9765
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9063
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9063
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9057
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9057
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9003
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9003
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8836
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8836
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8589
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8589
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8425
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8425
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8363
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8363
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8307
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8307
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.8223
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.8223
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8116
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8116
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8058
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8058
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8058
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8058
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8019
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8019
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7997
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7997
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7936
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7936
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7923
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7923
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7908
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7908
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7872
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7872
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7851
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7851
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7850
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7850
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7791
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7791
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7788
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7788
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7758
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7758
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7740
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7740
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7729
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7729
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7692
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7692
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7684
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7684
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7669
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7669
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7621
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7621
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7590
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7590
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7565
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7565
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7547
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7547
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7529
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7529
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7508
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7508
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7495
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7495
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7451
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7451
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7404
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7404
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7396
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7396
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.7393
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.7393
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7383
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7383
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7369
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7369
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7326
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7326
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7303
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7303
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7294
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7294
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7291
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7291
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7287
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7287
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7285
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7285
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7271
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7271
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7266
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7266
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7255
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7255
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7255
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7255
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7225
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7225
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7209
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7209
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7197
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7197
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7188
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7188
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7159
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7159
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7144
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7144
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7143
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7143
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7114
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7114
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7105
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7105
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7084
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7084
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7081
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7081
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7074
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7074
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7072
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7072
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7051
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7051
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.7034
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.7034
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7030
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7030
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7029
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7029
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7027
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7027

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