ChemSpider 2D Image | (4Z,6Z,8S,9S,10Z,12S,13R,14S,16R)-19-{[2-(Dimethylamino)ethyl]amino}-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 | C32H48N4O8

(4Z,6Z,8S,9S,10Z,12S,13R,14S,16R)-19-{[2-(Dimethylamino)ethyl]amino}-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 FormulaC32H48N4O8
  • Average mass616.745 Da
  • Monoisotopic mass616.347229 Da
  • ChemSpider ID29341696

  • 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-{[2-(Dimethylamino)ethyl]amino}-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-{[2-(Dimethylamino)ethyl]amino}-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]-19-[[2-(dimethylamino)ethyl]amino]-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-, (4Z,6Z,8S,9S,10Z,12S,13R,1 4S,16R)- [ACD/Index Name]
Carbamate de (4Z,6Z,8S,9S,10Z,12S,13R,14S,16R)-19-{[2-(diméthylamino)éthyl]amino}-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-y le [French] [ACD/IUPAC Name]
[(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-21-[2-(dimethylamino)ethylamino]-6-hydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate
150270-08-9 [RN]
17-[2-(DIMETHYLAMINO)ETHYL]AMINO-17-DESMETHOXYGELDANAMYCIN
17-Dimethylaminoethylamino-17-demethoxygeldanamycin [Wiki]
17-Dimethylaminogeldanamycin
17-DMAG; KOS-1022; NSC 707545
More...

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

17DMAG [DBID]
KOS-1022 [DBID]
NSC 707545 [DBID]
UNII:001L2FE0M3 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A 19-membered macrocyle that is geldanamycin in which the methoxy group attached to the benzoquinone moiety has been replaced by a 2-(N,N-dimethylamino)ethylamino; group. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65324

    • Bio Activity:

      Alvespimycin (17-DMAG; KOS-1022; NSC 707545) is a potent, water-soluble HSP90 inhibitor with IC50 of 62 nM. MedChem Express
      Alvespimycin (17-DMAG; KOS-1022; NSC 707545) is a potent, water-soluble HSP90 inhibitor with IC50 of 62 nM.; IC50 Value: 62 nM; Target: HSP90; in vitro: 17-DMAG displays ~2 times potency against human Hsp90 than 17-AAG, with IC50 of 62 nM versus 119 nM. MedChem Express HY-10389
      Alvespimycin (17-DMAG; KOS-1022; NSC 707545) is a potent, water-soluble HSP90 inhibitor with IC50 of 62 nM.;IC50 Value: 62 nM;Target: HSP90;In vitro: 17-DMAG displays ~2 times potency against human Hsp90 than 17-AAG, with IC50 of 62 nM versus 119 nM. In SKBR3 and SKOV3 cells which over-express Hsp90 client protein Her2, 17-DMAG causes down-regulation of Her2 with EC50 of 8 nM and 46 nM, respectively, as well as induction of Hsp70 with EC50 of 4 nM and 14 nM, respectively, leading to significant cytotoxicity with GI50 of 29 nM and 32 nM, respectively, consistent with Hsp90 inhibition. 17-DMAG in combination with vorinostat synergistically induces apoptosis of the cultured MCL cells as well as primary MCL cells, more potently than either agent alone, by markedly attenuating the levels of cyclin D1 and CDK4, as well as of c-Myc, c-RAF and Akt. ;In vivo: 17-DMAG treatment at 5 mg/kg or 25 mg/kg thrice per week significantly reduces tumor growth of TMK-1 xenografts, by significantly r MedChem Express HY-10389
      Cell Cycle/DNA Damage MedChem Express HY-10389
      Cell Cycle/DNA Damage; Metabolism/Protease; MedChem Express HY-10389
      HSP MedChem Express HY-10389

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.2±0.1 g/cm3
Boiling Point: 810.5±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±6.6 mmHg at 25°C
Enthalpy of Vaporization: 134.2±6.0 kJ/mol
Flash Point: 444.0±34.3 °C
Index of Refraction: 1.566
Molar Refractivity: 166.4±0.4 cm3
#H bond acceptors: 12
#H bond donors: 5
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 3
ACD/LogP: 2.07
ACD/LogD (pH 5.5): -0.54
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): 0.88
ACD/BCF (pH 7.4): 1.21
ACD/KOC (pH 7.4): 14.97
Polar Surface Area: 170 Å2
Polarizability: 66.0±0.5 10-24cm3
Surface Tension: 52.2±5.0 dyne/cm
Molar Volume: 510.3±5.0 cm3

Click to predict properties on the Chemicalize site


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