NP-MRD: Showing NP-Card for {[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid (NP0281728)

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Record Information

Version

1.0

Created at

2022-09-09 08:15:41 UTC

Updated at

2022-09-09 08:15:41 UTC

NP-MRD ID

NP0281728

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid

Description

Alvespimycin, also known as 17-DMAG, belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. It is shown to reduce the levels of CDK4 and ERBB2. Alvespimycin is a very strong basic compound (based on its pKa). In comparison to the first HSP90 inhibitor tanespimycin, it exhibits some pharmacologically desirable properties such as reduced metabolic liability, lower plasma protein binding, increased water solubility, higher oral bioavailability, reduced hepatotoxicity and superior antitumor activity. Alvespimycin mediates an antitumor activity through HSP90 inhibition that targets client proteins for proteasomal destruction, including oncogenic kinases such as BRAF. Common adverse effects include nausea, vomiting, fatigue, hematologic toxicity, liver enzyme disturbances and ocular disturbances including blurred vision and keratitis. They are often over-expressed or mutated in tumors, and contribute to cancer progression and therapy resistance. The administration of the drug is shown to result in the depletion of client proteins that have oncogenic activity and potential induction of HSP70 (HSP72). {[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid is found in Cullen corylifolium. It was first documented in 2009 (PMID: 19371599). However in vivo and in vitro studies suggest that weak metabolism of alvespimysin occurs in humans (PMID: 21278242) (PMID: 21663398) (PMID: 21718076) (PMID: 22547655).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041406322D          

 54 55  0  0  1  0            999 V2000
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 25 51  1  1  0  0  0
 26 52  1  6  0  0  0
 28 53  1  6  0  0  0
 30 54  1  6  0  0  0
M  END

     RDKit          3D

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  6 47  1  1
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  8 50  1  0
  9 51  1  0
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 19 67  1  0
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 20 69  1  0
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 25 74  1  0
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 27 77  1  0
 28 78  1  0
 28 79  1  0
 28 80  1  0
 31 81  1  0
 35 82  1  0
 37 83  1  0
 37 84  1  0
 37 85  1  0
 38 86  1  0
 16 59  1  0
 16 60  1  0
 16 61  1  0
M  END


  Mrv0541 05041406322D          

 54 55  0  0  1  0            999 V2000
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6992   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3815   -4.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6011   -2.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3247   -1.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5178   -1.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7372   -2.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7171   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4315   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1852   -2.8105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8334   -4.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5388   -5.3931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1102   -5.3621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9488   -3.1229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8514   -4.1404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6603   -0.7293    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4064   -2.4720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5577   -2.2837    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2440   -5.0933    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9720   -4.5779    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9895   -2.6267    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -7.0125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1370   -4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 11  9  2  0  0  0  0
 13 12  1  0  0  0  0
 18  1  1  1  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19  2  1  0  0  0  0
 19 10  2  0  0  0  0
 20  3  1  1  0  0  0
 20 16  1  0  0  0  0
 21  4  1  0  0  0  0
 21 16  2  0  0  0  0
 22 14  1  0  0  0  0
 23 17  2  0  0  0  0
 24 17  1  0  0  0  0
 25 11  1  0  0  0  0
 26 15  1  0  0  0  0
 27 22  2  0  0  0  0
 27 24  1  0  0  0  0
 28 20  1  0  0  0  0
 28 26  1  0  0  0  0
 29 22  1  0  0  0  0
 29 23  1  0  0  0  0
 30 21  1  0  0  0  0
 30 25  1  0  0  0  0
 31 19  1  0  0  0  0
 33 32  2  0  0  0  0
 34 12  1  0  0  0  0
 34 27  1  0  0  0  0
 35 23  1  4  0  0  0
 35 31  2  0  0  0  0
 36  5  1  0  0  0  0
 36  6  1  0  0  0  0
 36 13  1  0  0  0  0
 37 24  2  0  0  0  0
 28 38  1  1  0  0  0
 39 29  2  0  0  0  0
 40 31  1  0  0  0  0
 41 32  1  0  0  0  0
 42  7  1  0  0  0  0
 25 42  1  6  0  0  0
 43  8  1  0  0  0  0
 26 43  1  1  0  0  0
 30 44  1  1  0  0  0
 44 32  1  0  0  0  0
 45  9  1  0  0  0  0
 46 10  1  0  0  0  0
 47 11  1  0  0  0  0
 48 16  1  0  0  0  0
 18 49  1  6  0  0  0
 20 50  1  6  0  0  0
 25 51  1  1  0  0  0
 26 52  1  6  0  0  0
 28 53  1  6  0  0  0
 30 54  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0281728

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]/C1=C([H])/[C@]([H])(OC)[C@@]([H])(OC(O)=N)\C(C)=C([H])\[C@]([H])(C)[C@@]([H])(O)[C@]([H])(C[C@]([H])(C)CC2=C(NCCN(C)C)C(=O)C=C(N=C(O)\C(C)=C\1/[H])C2=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C32H48N4O8/c1-18-14-22-27(34-12-13-36(5)6)24(37)17-23(29(22)39)35-31(40)19(2)10-9-11-25(42-7)30(44-32(33)41)21(4)16-20(3)28(38)26(15-18)43-8/h9-11,16-18,20,25-26,28,30,34,38H,12-15H2,1-8H3,(H2,33,41)(H,35,40)/b11-9-,19-10+,21-16+/t18-,20+,25+,26+,28-,30+/m1/s1

> <INCHI_KEY>
KUFRQPKVAWMTJO-LMZWQJSESA-N

> <FORMULA>
C32H48N4O8

> <MOLECULAR_WEIGHT>
616.7455

> <EXACT_MASS>
616.347214532

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
65.38277894988585

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
2.7794863695921217

> <ALOGPS_LOGS>
-4.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
8.271302374330624

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.5466001698362835

> <JCHEM_PKA_STRONGEST_BASIC>
6.995227199338757

> <JCHEM_POLAR_SURFACE_AREA>
174

> <JCHEM_REFRACTIVITY>
184.1065

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   37  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   45  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5   36                                                            
CONECT    6   36                                                            
CONECT    7   42                                                            
CONECT    8   43                                                            
CONECT    9   10   11   45                                                  
CONECT   10    9   19   46                                                  
CONECT   11    9   25   47                                                  
CONECT   12   13   34                                                       
CONECT   13   12   36                                                       
CONECT   14   18   22                                                       
CONECT   15   18   26                                                       
CONECT   16   20   21   48                                                  
CONECT   17   23   24                                                       
CONECT   18    1   14   15   49                                             
CONECT   19    2   10   31                                                  
CONECT   20    3   16   28   50                                             
CONECT   21    4   16   30                                                  
CONECT   22   14   27   29                                                  
CONECT   23   17   29   35                                                  
CONECT   24   17   27   37                                                  
CONECT   25   11   30   42   51                                             
CONECT   26   15   28   43   52                                             
CONECT   27   22   24   34                                                  
CONECT   28   20   26   38   53                                             
CONECT   29   22   23   39                                                  
CONECT   30   21   25   44   54                                             
CONECT   31   19   35   40                                                  
CONECT   32   33   41   44                                                  
CONECT   33   32                                                            
CONECT   34   12   27                                                       
CONECT   35   23   31                                                       
CONECT   36    5    6   13                                                  
CONECT   37   24                                                            
CONECT   38   28                                                            
CONECT   39   29                                                            
CONECT   40   31                                                            
CONECT   41   32                                                            
CONECT   42    7   25                                                       
CONECT   43    8   26                                                       
CONECT   44   30   32                                                       
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   11                                                            
CONECT   48   16                                                            
CONECT   49   18                                                            
CONECT   50   20                                                            
CONECT   51   25                                                            
CONECT   52   26                                                            
CONECT   53   28                                                            
CONECT   54   30                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  110    0
END

View in JSmol

Synonyms

Value	Source
17-(Dimethylaminoethylamino)-17-demethoxygeldanamycin	ChEBI
17-DMAG	ChEBI
17-(dimethylaminoethylamino)-17-Demethoxy-geldanamycin	MeSH
17-Desmethoxy-17-N,N-dimethylaminoethylamino-geldanamycin	MeSH
17DMAG	MeSH
17-dimethylaminoethylamino-17-Demethoxy-geldanamycin	MeSH

Chemical Formula

C₃₂H₄₈N₄O₈

Average Mass

616.7455 Da

Monoisotopic Mass

616.34721 Da

IUPAC Name

{[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]/C1=C([H])/[C@]([H])(OC)[C@@]([H])(OC(O)=N)\C(C)=C([H])\[C@]([H])(C)[C@@]([H])(O)[C@]([H])(C[C@]([H])(C)CC2=C(NCCN(C)C)C(=O)C=C(N=C(O)\C(C)=C\1/[H])C2=O)OC

InChI Identifier

InChI=1S/C32H48N4O8/c1-18-14-22-27(34-12-13-36(5)6)24(37)17-23(29(22)39)35-31(40)19(2)10-9-11-25(42-7)30(44-32(33)41)21(4)16-20(3)28(38)26(15-18)43-8/h9-11,16-18,20,25-26,28,30,34,38H,12-15H2,1-8H3,(H2,33,41)(H,35,40)/b11-9-,19-10+,21-16+/t18-,20+,25+,26+,28-,30+/m1/s1

InChI Key

KUFRQPKVAWMTJO-LMZWQJSESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cullen corylifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolactams

Sub Class

Not Available

Direct Parent

Macrolactams

Alternative Parents

Substituents

Macrolactam
Vinylogous amide
Carbamic acid ester
Amino acid or derivatives
Carboxamide group
Ketone
Lactam
Carbonic acid derivative
Secondary alcohol
Cyclic ketone
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxylic acid derivative
Dialkyl ether
Secondary aliphatic amine
Enamine
Ether
Azacycle
Organoheterocyclic compound
Secondary amine
Carbonyl group
Organic nitrogen compound
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:65324 )
secondary amino compound (CHEBI:65324 )
lactam (CHEBI:65324 )
macrocycle (CHEBI:65324 )
benzoquinones (CHEBI:65324 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.08	ALOGPS
logP	2.78	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.55	ChemAxon
pKa (Strongest Basic)	7	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	174 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	184.11 m³·mol⁻¹	ChemAxon
Polarizability	65.38 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB12442

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

17-Dimethylaminoethylamino-17-demethoxygeldanamycin

METLIN ID

Not Available

PubChem Compound

5288674

PDB ID

Not Available

ChEBI ID

65324

Good Scents ID

Not Available

References

General References

Wu YC, Yen WY, Lee TC, Yih LH: Heat shock protein inhibitors, 17-DMAG and KNK437, enhance arsenic trioxide-induced mitotic apoptosis. Toxicol Appl Pharmacol. 2009 Apr 15;236(2):231-8. doi: 10.1016/j.taap.2009.02.003. Epub 2009 Feb 12. [PubMed:19371599 ]
Pacey S, Wilson RH, Walton M, Eatock MM, Hardcastle A, Zetterlund A, Arkenau HT, Moreno-Farre J, Banerji U, Roels B, Peachey H, Aherne W, de Bono JS, Raynaud F, Workman P, Judson I: A phase I study of the heat shock protein 90 inhibitor alvespimycin (17-DMAG) given intravenously to patients with advanced solid tumors. Clin Cancer Res. 2011 Mar 15;17(6):1561-70. doi: 10.1158/1078-0432.CCR-10-1927. Epub 2011 Jan 28. [PubMed:21278242 ]
Fukumoto R, Kiang JG: Geldanamycin analog 17-DMAG limits apoptosis in human peripheral blood cells by inhibition of p53 activation and its interaction with heat-shock protein 90 kDa after exposure to ionizing radiation. Radiat Res. 2011 Sep;176(3):333-45. doi: 10.1667/rr2534.1. Epub 2011 Jun 10. [PubMed:21663398 ]
Goldstein S: One-electron reduction of 17-(dimethylaminoethylamino)-17-demethoxygeldanamycin: a pulse radiolysis study. J Phys Chem A. 2011 Aug 18;115(32):8928-32. doi: 10.1021/jp205161v. Epub 2011 Jul 22. [PubMed:21718076 ]
Madrigal-Matute J, Fernandez-Garcia CE, Gomez-Guerrero C, Lopez-Franco O, Munoz-Garcia B, Egido J, Blanco-Colio LM, Martin-Ventura JL: HSP90 inhibition by 17-DMAG attenuates oxidative stress in experimental atherosclerosis. Cardiovasc Res. 2012 Jul 1;95(1):116-23. doi: 10.1093/cvr/cvs158. Epub 2012 Apr 30. [PubMed:22547655 ]
LOTUS database [Link]

Showing NP-Card for {[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid (NP0281728)

MOL for NP0281728 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

3D MOL for NP0281728 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

3D SDF for NP0281728 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

3D-SDF for NP0281728 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

PDB for NP0281728 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

3D PDB for NP0281728 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

SMILES for NP0281728 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

INCHI for NP0281728 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

Structure for NP0281728 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)

3D Structure for NP0281728 ({[(4e,6z,8s,9s,10e,12s,13r,14s,16r)-19-{[2-(dimethylamino)ethyl]amino}-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid)