Natural Product (NP) Details

General Information of the NP (ID: NP9921)
Name
Ferutinin
Synonyms
Ferutinine; Ferutinin; 41743-44-6; Jaeschkeanadiol p-hydroxybenzoate; [(3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] 4-hydroxybenzoate; 4-Oxy-6-(4-oxybezoyloxy)dauc-8,9-en; From Ferula tingiatana; 4mg7; Isolated from the plant Ferula tenuisecta; CHEMBL465040; Ferutinin, >=98% (HPLC); SCHEMBL12512403; DTXSID20961947; Jaeschkeanadiol p-hydroxy benzoate; 3-Hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate; ZINC2564854; NSC606959; NSC-606959; Q27452770; (3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate; Benzoic acid, 4-hydroxy-, (3R,3aS,4S,8aR)-1,2,3,3a,4,5,8,8a-octahydro-3-hydroxy-6,8a-dimethyl-3-(1-methylethyl)-4-azulenyl ester; Benzoic acid, 4-hydroxy-, 1,2,3,3a,4,5,8,8a-octahydro-3-hydroxy-6,8a-dimethyl-3-(1-methylethyl)-4-azulenyl ester, (3R-(3alpha,3abeta,4beta,8aalpha))-
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Species Origin Ferula sinkiangensisK ...     Click to Show/Hide
Ferula sinkiangensisK
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Apiales
Family: Apiaceae
Genus: Ferula
Species: Ferula sinkiangensisK
Disease Breast cancer [ICD-11: 2C60] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.147
 
MDCK Permeability
 -4.852
 
PAMPA
 -
 
HIA
 - - -
 
Distribution
VDss
 0.268
 
PPB
 94.1%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 ++
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 - -
CYP3A4 substrate
 ++
CYP2B6 inhibitor
 +
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 +++
 
Excretion
CLplasma
 12.457
 
T1/2
 1.261
Toxicity
DILI
 - -
 
Rat Oral Acute Toxicity
 - - -
 
FDAMDD
 - -
 
Respiratory
 - -
 
Human Hepatotoxicity
 - -
 
Ototoxicity
 -
 
Drug-induced Nephrotoxicity
 -
 
Drug-induced Neurotoxicity
 - -
 
Hematotoxicity
 - - -
 
Genotoxicity
 - -
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C22H30O4
PubChem CID
354654
Canonical SMILES
CC1=CCC2(CCC(C2C(C1)OC(=O)C3=CC=C(C=C3)O)(C(C)C)O)C
InChI
1S/C22H30O4/c1-14(2)22(25)12-11-21(4)10-9-15(3)13-18(19(21)22)26-20(24)16-5-7-17(23)8-6-16/h5-9,14,18-19,23,25H,10-13H2,1-4H3/t18-,19+,21-,22+/m0/s1
InChIKey
CYSHNJQMYORNJI-YUVXSKOASA-N
CAS Number
CAS 41743-44-6
Herb ID
HBIN026483
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Streptomycin      Bacterial infection     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)		 The combination of 1 with each antitubercular drug led to mutual enhancement of the antimycobacterial activity with isoniazid and ethionamide, while no such effect was observed with rifampin or streptomycin.
          Ethionamide      HIV-infected patients with tuberculosis     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)		 The combination of 1 with each antitubercular drug led to mutual enhancement of the antimycobacterial activity with isoniazid and ethionamide, while no such effect was observed with rifampin or streptomycin.
          Isoniazid      HIV-infected patients with tuberculosis     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)		 The combination of 1 with each antitubercular drug led to mutual enhancement of the antimycobacterial activity with isoniazid and ethionamide, while no such effect was observed with rifampin or streptomycin.
          Rifampicin      HIV-infected patients with tuberculosis     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)		 The combination of 1 with each antitubercular drug led to mutual enhancement of the antimycobacterial activity with isoniazid and ethionamide, while no such effect was observed with rifampin or streptomycin.
References
Reference 1 A ferutinin analogue with enhanced potency and selectivity against ER-positive breast cancer cells in vitro. Biomed Pharmacother. 2018 Sep;105:267-273.
Reference 2 Antimycobacterial activity of ferutinin alone and in combination with antitubercular drugs against a rapidly growing surrogate of Mycobacterium tuberculosis. Nat Prod Res. 2011 Jul;25(12):1142-9.
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