ChemSpider 2D Image | (4Z,6Z,8S,9S,10Z,12S,13R,14S,16R)-19-(Allylamino)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate | C31H43N3O8

(4Z,6Z,8S,9S,10Z,12S,13R,14S,16R)-19-(Allylamino)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate

  • Molecular FormulaC31H43N3O8
  • Average mass585.688 Da
  • Monoisotopic mass585.304993 Da
  • ChemSpider ID28426472
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 6 of 6 defined stereocentres


More details:






Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(4Z,6Z,8S,9S,10Z,12S,13R,14S,16R)-19-(Allylamino)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate [ACD/IUPAC Name]
(4Z,6Z,8S,9S,10Z,12S,13R,14S,16R)-19-(Allylamino)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-ylcarbamat [German] [ACD/IUPAC Name]
2-Azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9-[(aminocarbonyl)oxy]-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-19-(2-propen-1-ylamino)-, (4Z,6Z,8S,9S,10Z,12S,13R,14S,16R)- [ACD/Index Name]
Carbamate de (4Z,6Z,8S,9S,10Z,12S,13R,14S,16R)-19-(allylamino)-13-hydroxy-8,14-diméthoxy-4,10,12,16-tétraméthyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaén-9-yle [French] [ACD/IUPAC Name]
(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-(Allylamino)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate [ACD/IUPAC Name]
[75747-14-7]
17 AAG
17-(Allylamino)-17-demethoxygeldanamycin
17-(Allylamino)-17-desmethylgeldanamycin
17-(ALLYLAMINO-D5)GELDANAMYCIN
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

17-AAG [DBID]
CP 127374 [DBID]
NSC 330507 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A 19-membered macrocyle that is geldanamycin in which the methoxy substituent attached to the benzoquinone moiety has been replaced by an allylamino group. It is a potent inhibitor of heat shock prote in 90 (Hsp90). A less toxic analogue than geldanamycin, it induces apoptosis and displays antitumour effects. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:64153
    • Bio Activity:

      17-AAG(NSC 330507; CP 127374) is a potent HSP90 inhibitor with IC50 of 5 nM, having a 100-fold higher binding affinity for HSP90 derived from tumour cells than HSP90 from normal cells. MedChem Express
      17-AAG(NSC 330507; CP 127374) is a potent HSP90 inhibitor with IC50 of 5 nM, having a 100-fold higher binding affinity for HSP90 derived from tumour cells than HSP90 from normal cells.; IC50 Value: 5 nM; Target: HSP90; in vitro: 17-AAG, an analog of geldanamycin, exhibits greater than 100 times higher binding affinity for Hsp90 derived from HER-2-overexpressing cancer cells (BT474, N87, SKOV3 and SKBR3) or BT474 breast carcinoma cells with IC50 values of 5-6 nM. MedChem Express HY-10211
      Cell Biology Tocris Bioscience 1515
      Cell Cycle/DNA Damage MedChem Express HY-10211
      Cell Cycle/DNA Damage; Metabolism/Protease; MedChem Express HY-10211
      Heat Shock Proteins Tocris Bioscience 1515
      HSP MedChem Express HY-10211
      Inhibitor of heat shock protein 90 (Hsp90) chaperone activity, and an analog of geldanamycin (Cat. No. 1368). Subsequently inhibits the activity of oncogenic proteins such as p185erbB-2 (IC50 = 31 nM), N-ras, Ki-ras and c-Akt. Antitumor in vivo. Also protects neuroprogenitor cells against stress-induced apoptosis at low concentrations (10 nM) in vitro. Tocris Bioscience 1515
      Signal Transduction Tocris Bioscience 1515

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.2±0.1 g/cm3
Boiling Point: 797.8±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±6.4 mmHg at 25°C
Enthalpy of Vaporization: 132.2±6.0 kJ/mol
Flash Point: 436.3±32.9 °C
Index of Refraction: 1.566
Molar Refractivity: 157.7±0.4 cm3
#H bond acceptors: 11
#H bond donors: 5
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 3
ACD/LogP: 2.68
ACD/LogD (pH 5.5): 2.88
ACD/BCF (pH 5.5): 91.76
ACD/KOC (pH 5.5): 883.97
ACD/LogD (pH 7.4): 2.87
ACD/BCF (pH 7.4): 89.20
ACD/KOC (pH 7.4): 859.29
Polar Surface Area: 166 Å2
Polarizability: 62.5±0.5 10-24cm3
Surface Tension: 51.4±5.0 dyne/cm
Molar Volume: 483.3±5.0 cm3

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