Detailed information for compound 444780

Basic information

Technical information
  • TDR Targets ID: 444780
  • Name: (3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS )-3-acetyloxy-4,6a,6b,8a,11,12,14b-heptamethy l-14-oxo-1,2,3,4a,5,6,7,8,9,10,11,12,12a,14a- tetradecahydropicene-4-carboxylic acid
  • MW: 512.721 | Formula: C32H48O5
  • H donors: 1 H acceptors: 4 LogP: 7.22 Rotable bonds: 3
    Rule of 5 violations (Lipinski): 2
  • SMILES: CC(=O)O[C@@H]1CC[C@]2([C@H]([C@@]1(C)C(=O)O)CC[C@@]1([C@@H]2C(=O)C=C2[C@@]1(C)CC[C@@]1([C@H]2[C@@H](C)[C@H](C)CC1)C)C)C
  • InChi: 1S/C32H48O5/c1-18-9-12-28(4)15-16-30(6)21(25(28)19(18)2)17-22(34)26-29(5)13-11-24(37-20(3)33)32(8,27(35)36)23(29)10-14-31(26,30)7/h17-19,23-26H,9-16H2,1-8H3,(H,35,36)/t18-,19+,23-,24-,25+,26-,28-,29+,30-,31-,32-/m1/s1
  • InChiKey: HMMGKOVEOFBCAU-BCDBGHSCSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-acetoxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4a,5,6,7,8,9,10,11,12,12a,14a-tetradecahydropicene-4-carboxylic acid
  • (3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-acetoxy-14-keto-4,6a,6b,8a,11,12,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,11,12,12a,14a-tetradecahydropicene-4-carboxylic acid
  • acetyl-11-ketoboswellic acid
  • 3-O-Acetyl-11-keto-beta-Boswellic Acid
  • AKbetaBA
  • Acetyl-11-keto-beta-Boswellic Acid, Boswellia serrata
  • Curator_000001

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens arachidonate 5-lipoxygenase Starlite/ChEMBL References
Homo sapiens prolyl endopeptidase Starlite/ChEMBL References
Homo sapiens prostaglandin E synthase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Schistosoma mansoni prolyl oligopeptidase (S09 family) Get druggable targets OG5_129295 All targets in OG5_129295
Echinococcus granulosus arachidonate 5 lipoxygenase Get druggable targets OG5_127482 All targets in OG5_127482
Leishmania major prolyl oligopeptidase, putative,serine peptidase clan SC, family S9A, putative Get druggable targets OG5_129295 All targets in OG5_129295
Leishmania donovani prolyl endopeptidase Get druggable targets OG5_129295 All targets in OG5_129295
Echinococcus multilocularis arachidonate 5 lipoxygenase Get druggable targets OG5_127482 All targets in OG5_127482
Schistosoma japonicum ko:K00799 glutathione S-transferase [EC2.5.1.18], putative Get druggable targets OG5_131112 All targets in OG5_131112
Schistosoma japonicum ko:K00799 glutathione S-transferase [EC2.5.1.18], putative Get druggable targets OG5_131112 All targets in OG5_131112
Trypanosoma cruzi prolyl endopeptidase Get druggable targets OG5_129295 All targets in OG5_129295
Leishmania mexicana prolyl oligopeptidase, putative Get druggable targets OG5_129295 All targets in OG5_129295
Schistosoma japonicum ko:K01322 prolyl oligopeptidase [EC3.4.21.26], putative Get druggable targets OG5_129295 All targets in OG5_129295
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_129295 All targets in OG5_129295
Onchocerca volvulus Prolyl endopeptidase homolog Get druggable targets OG5_129295 All targets in OG5_129295
Trypanosoma congolense prolyl endopeptidase Get druggable targets OG5_129295 All targets in OG5_129295
Trypanosoma brucei prolyl endopeptidase Get druggable targets OG5_129295 All targets in OG5_129295
Mycobacterium tuberculosis Probable protease II PtrBa [first part] (oligopeptidase B) Get druggable targets OG5_129295 All targets in OG5_129295
Schistosoma japonicum ko:K00461 arachidonate 5-lipoxygenase [EC1.13.11.34], putative Get druggable targets OG5_127482 All targets in OG5_127482
Schistosoma mansoni lipoxygenase Get druggable targets OG5_127482 All targets in OG5_127482
Schistosoma japonicum IPR001024,Lipoxygenase, LH2;IPR013819,Lipoxygenase, C-terminal,domain-containing Get druggable targets OG5_127482 All targets in OG5_127482
Echinococcus multilocularis prolyl endopeptidase Get druggable targets OG5_129295 All targets in OG5_129295
Schistosoma japonicum Prolyl endopeptidase, putative Get druggable targets OG5_129295 All targets in OG5_129295
Leishmania infantum prolyl oligopeptidase, putative,serine peptidase clan SC, family S9A, putative Get druggable targets OG5_129295 All targets in OG5_129295
Toxoplasma gondii prolyl endopeptidase Get druggable targets OG5_129295 All targets in OG5_129295
Schistosoma mansoni membrane associated proteins in eicosanoid and glutathione metabolism family member Get druggable targets OG5_131112 All targets in OG5_131112
Echinococcus granulosus prolyl endopeptidase Get druggable targets OG5_129295 All targets in OG5_129295
Schistosoma mansoni lipoxygenase Get druggable targets OG5_127482 All targets in OG5_127482
Trypanosoma brucei gambiense prolyl oligopeptidase, putative,serine peptidase clan SC, family S9A, putative Get druggable targets OG5_129295 All targets in OG5_129295
Schistosoma mansoni prolyl oligopeptidase (S09 family) Get druggable targets OG5_129295 All targets in OG5_129295
Brugia malayi prolyl oligopeptidase family protein Get druggable targets OG5_129295 All targets in OG5_129295
Neospora caninum Prolyl oligopeptidase (EC 3.4.21.26) (Precursor), related Get druggable targets OG5_129295 All targets in OG5_129295
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Trypanosoma brucei oligopeptidase b prolyl endopeptidase 710 aa 630 aa 27.0 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Onchocerca volvulus Prolyl endopeptidase homolog 0.0158 0.103 1
Toxoplasma gondii prolyl endopeptidase 0.0158 0.103 1
Echinococcus granulosus prolyl endopeptidase 0.0158 0.103 0.103
Schistosoma mansoni hypothetical protein 0.0897 0.8624 1
Plasmodium vivax kinesin-5 0.0134 0.0781 0.5
Echinococcus multilocularis arachidonate 5 lipoxygenase 0.0142 0.0869 0.0869
Schistosoma mansoni prolyl oligopeptidase (S09 family) 0.0158 0.103 0.1195
Brugia malayi prolyl oligopeptidase family protein 0.0158 0.103 1
Schistosoma mansoni lipoxygenase 0.0142 0.0869 0.1008
Echinococcus multilocularis microsomal glutathione S transferase 3 0.0135 0.0794 0.0794
Plasmodium falciparum kinesin-5 0.0134 0.0781 0.5
Leishmania major prolyl oligopeptidase, putative,serine peptidase clan SC, family S9A, putative 0.0158 0.103 1
Loa Loa (eye worm) hypothetical protein 0.0158 0.103 1
Toxoplasma gondii MAPEG family protein 0.0135 0.0794 0.0515
Schistosoma mansoni kinesin eg-5 0.0134 0.0781 0.0906
Schistosoma mansoni microsomal glutathione s-transferase 0.0135 0.0794 0.0921
Schistosoma mansoni membrane associated proteins in eicosanoid and glutathione metabolism family member 0.059 0.5467 0.6339
Entamoeba histolytica kinesin, putative 0.0134 0.0781 0.5
Mycobacterium leprae PROBABLE PROTEASE II PTRBB (OLIGOPEPTIDASE B) 0.0063 0.0051 0.5
Echinococcus multilocularis kinesin family 1 0.1031 1 1
Schistosoma mansoni lipoxygenase 0.01 0.0428 0.0497
Echinococcus granulosus microsomal glutathione S transferase 3 0.0135 0.0794 0.0794
Echinococcus granulosus arachidonate 5 lipoxygenase 0.0142 0.0869 0.0869
Brugia malayi Kinesin motor domain containing protein 0.0134 0.0781 0.7582
Trypanosoma cruzi prolyl endopeptidase 0.0158 0.103 1
Schistosoma mansoni prolyl oligopeptidase (S09 family) 0.0158 0.103 0.1195
Loa Loa (eye worm) kinesin-like protein KLP2 0.0134 0.0781 0.7582
Giardia lamblia Kinesin-5 0.0134 0.0781 0.5
Echinococcus multilocularis prolyl endopeptidase 0.0158 0.103 0.103
Mycobacterium ulcerans protease II (oligopeptidase B), PtrB 0.0063 0.0051 0.5
Mycobacterium tuberculosis Probable protease II PtrBa [first part] (oligopeptidase B) 0.0142 0.086 1
Trypanosoma brucei prolyl endopeptidase 0.0158 0.103 1

Activities

Activity type Activity value Assay description Source Reference
Activity (ADMET) = 81.15 % Cytotoxicity against mouse RAW264.7 cells assessed as cell viability at 100 uM after 24 hrs by MTT assay relative to control ChEMBL. 23391590
GI (functional) = 59 % Anticancer activity against human Hep2 cells assessed as growth inhibition at 50 uM after 48 hrs by SRB assay ChEMBL. 22123322
GI (functional) = 76 % Anticancer activity against human PC3 cells assessed as growth inhibition at 50 uM after 48 hrs by SRB assay ChEMBL. 22123322
GI (functional) = 85 % Anticancer activity against human COLO205 cells assessed as growth inhibition at 50 uM after 48 hrs by SRB assay ChEMBL. 22123322
GI (functional) = 85 % Anticancer activity against human DU145 cells assessed as growth inhibition at 50 uM after 48 hrs by SRB assay ChEMBL. 22123322
GI (functional) = 88 % Anticancer activity against human HT-29 cells assessed as growth inhibition at 50 uM after 48 hrs by SRB assay ChEMBL. 22123322
GI (functional) = 88 % Anticancer activity against human SW620 cells assessed as growth inhibition at 50 uM after 48 hrs by SRB assay ChEMBL. 22123322
IC50 (binding) = 2.7 uM Inhibition of lipoxygenase 5 product formation from endogenous substrate in Calcium and ionophore-stimulated polymorphonuclear leukocyte ChEMBL. 10978197
IC50 (binding) = 3 uM Inhibition of microsomal PGES1 isolated from IL-1beta-stimulated human A549 cells preincubated for 15 mins followed by substrate addition measured after 1 min by RP-HPLC analysis ChEMBL. 24844534
IC50 (functional) = 7.45 uM Antiproliferation activity against HUVEC cells after 48 hrs by CCK-8 assay ChEMBL. 25819335
IC50 (binding) = 7.89 uM Inhibition of prolyl endopeptidase ChEMBL. 15730241
IC50 (functional) = 11 uM Cytotoxicity against human HL60 cells after 48 hrs by MTT assay ChEMBL. 21334793
IC50 (functional) = 15.6 uM Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production after 24 hrs ChEMBL. 23391590
IC50 (functional) = 19.4 uM Cytotoxicity against human HT-29 cells assessed as cell survival after 96 hrs by SRB assay ChEMBL. 25618017
IC50 (functional) = 31 uM Cytotoxicity against human HeLa cells after 48 hrs by MTT assay ChEMBL. 21334793
Inhibition (functional) = 2 % Cytotoxicity against human SW620 cells at 10 uM after 48 hrs ChEMBL. 17950603
Inhibition (functional) = 2 % Cytotoxicity against human SW620 cells at 10 uM after 48 hrs ChEMBL. 17950603
Inhibition (functional) = 8 % Cytotoxicity against human 502713 cells at 10 uM after 48 hrs ChEMBL. 17950603
Inhibition (functional) = 10 % Cytotoxicity against human DU145 cells at 10 uM after 48 hrs ChEMBL. 17950603
Inhibition (functional) = 10 % Cytotoxicity against human DU145 cells at 10 uM after 48 hrs ChEMBL. 17950603
Inhibition (functional) = 12 % Cytotoxicity against human MCF7 cells at 10 uM after 48 hrs ChEMBL. 17950603
Inhibition (functional) = 12 % Cytotoxicity against human MCF7 cells at 10 uM after 48 hrs ChEMBL. 17950603
Inhibition (functional) = 24 % Cytotoxicity against human HT29 cells at 10 uM after 48 hrs ChEMBL. 17950603
Inhibition (functional) = 24 % Cytotoxicity against human HT29 cells at 10 uM after 48 hrs ChEMBL. 17950603
Inhibition (binding) = 40 % Inhibition of VEGFR-2 (unknown origin) at 50 uM after 1 hr by luminescence assay ChEMBL. 25819335
Inhibition (binding) = 52 % Inhibition of human recombinant 11beta-HSD2 expressed in HEK293 cells assessed as reduction of cortisone to cortisol conversion at 20 uM by scintillation counting ChEMBL. 20100662
Inhibition (functional) = 53.93 % Anti-inflammatory activity in human PBMC assessed as inhibition of LPS-induced IL-6 expression at 10 uM after 5 hrs ChEMBL. 26711891
Inhibition (binding) = 63 % Inhibition of human recombinant 11beta-HSD1 expressed in HEK293 cells assessed as reduction of cortisone to cortisol conversion at 20 uM by scintillation counting ChEMBL. 20100662
Inhibition (functional) = 70.7 % Anti-inflammatory activity in BALB/c mouse assessed as inhibition of LPS-induced TNFalpha expression at 10 mg/kg, po pre-treated for 1 hr followed by LPS administration measured 2.5 hrs after LPS challenge by ELISA ChEMBL. 26711891
permeability (ADMET) = 0.24 ng/cm2/min Permeability from apical to basolateral side of human Caco2 cells at 5 mg/mL ChEMBL. 23013292

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Homo sapiens ChEMBL23 21334793
Mus musculus ChEMBL23 23391590

Many chemical entities in TDR Targets come from high-throughput screenings with whole cells or tissue samples, and not all assayed compounds have been tested against a single a single target protein, probably because they get ruled out during screening process. Even if these compounds may have not been of interest in the original screening, they may come as interesting leads for other screening assays. Furthermore, we may be able to propose drug-target associations using chemical similarities and network patterns.

Annotated phenotypes:

We have no manually annotated phenotypes for this drug. What does this mean? / Care to help?
In TDR Targets, information about phenotypes that are caused by drugs, or by genetic manipulation of cells (e.g. gene knockouts or knockdowns) is manually curated from the literature. These descriptions help to describe the potential of the target for drug development. If no information is available for this gene or if the information is incomplete, this may mean that i) the papers containing this information either appeared after the curation effort for this organism was carried out or they were inadvertently missed by curators; or that ii) the curation effort for this organism has not yet started.
 
In any case, if you have information about papers containing relevant validation data for this target, please log in using your TDR Targets username and password and send them to us using the corresponding form in this page (only visible to registered users) or contact us.

External resources for this compound

Bibliographic References

6 literature references were collected for this gene.

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