NP-MRD: Showing NP-Card for methyl (2e,4e,8e)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(c-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate (NP0187096)

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Record Information

Version

2.0

Created at

2022-09-04 03:08:50 UTC

Updated at

2022-09-04 03:08:50 UTC

NP-MRD ID

NP0187096

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2e,4e,8e)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(c-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate

Description

Methyl geldanamycinate belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. methyl (2e,4e,8e)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(c-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate is found in Streptomyces hygroscopicus. Based on a literature review very few articles have been published on Methyl geldanamycinate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042205082D          

 42 42  0  0  0  0            999 V2000
   -2.1434  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 30 39  1  0  0  0  0
 39 40  2  0  0  0  0
 25 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END

     RDKit          3D

 86 86  0  0  0  0  0  0  0  0999 V2000
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    4.7466    2.0101   -3.6085 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4730    0.1811   -0.7664 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1363    0.7779   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8123    2.2238   -0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0576    0.0117   -1.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172    0.5548   -1.2864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7919    0.2114   -2.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2698   -0.0848   -0.3161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8301    0.0092    0.9862 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.8340    1.8043    1.7131 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8771    0.2876    1.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1559    1.2168    1.7752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8111    1.7525   -0.1479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2128    2.6015   -1.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1624    0.4305    0.5484 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2975   -0.5591    0.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447   -0.1815    0.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6787   -1.0942    0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9199   -0.7081    0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1570    0.7787    0.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0218   -1.6535    0.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7602   -2.8768    0.9534 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3442   -1.2711    1.1169 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4170   -2.1824    1.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3067    0.1988    1.6240 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3154    1.2959    2.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406    2.8508   -3.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6948    2.7875   -0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0760    2.2598    0.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2726   -1.1199   -1.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5046   -1.1222    2.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0025    2.2388    1.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
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 31 30  1  0
 30 14  1  0
 14 15  1  0
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 41 81  1  0
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 41 83  1  0
M  END


  Mrv1652309042205082D          

 42 42  0  0  0  0            999 V2000
   -2.1434  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 30 39  1  0  0  0  0
 39 40  2  0  0  0  0
 25 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0187096

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(CC(C)CC1=C(OC)C(=O)C=C(N)C1=O)C(O)C(C)\C=C(/C)C(OC(O)=N)C(OC)\C=C\C=C(/C)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C30H44N2O10/c1-16(12-20-26(35)21(31)15-22(33)28(20)40-7)13-24(39-6)25(34)18(3)14-19(4)27(42-30(32)37)23(38-5)11-9-10-17(2)29(36)41-8/h9-11,14-16,18,23-25,27,34H,12-13,31H2,1-8H3,(H2,32,37)/b11-9+,17-10+,19-14+

> <INCHI_KEY>
HRKSVRIGRTWRMY-LPCSBIKHSA-N

> <FORMULA>
C30H44N2O10

> <MOLECULAR_WEIGHT>
592.686

> <EXACT_MASS>
592.299595625

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
62.58663848002365

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2E,4E,8E)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(C-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate

> <JCHEM_LOGP>
0.6298410915584071

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.906875749470409

> <JCHEM_PKA_STRONGEST_ACIDIC>
-4.594863534922838

> <JCHEM_PKA_STRONGEST_BASIC>
10.788051265605743

> <JCHEM_POLAR_SURFACE_AREA>
187.69000000000003

> <JCHEM_REFRACTIVITY>
171.8538

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E,4E,8E)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(C-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001 -20.790   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001 -19.250   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667 -18.480   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334 -19.250   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.001 -10.010   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      12.003 -11.550   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   41                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   39                                                  
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   30   40                                                  
CONECT   40   39                                                            
CONECT   41   25   42                                                       
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   84    0
END

View in JSmol

Synonyms

Value	Source
Methyl geldanamycinic acid	Generator

Chemical Formula

C₃₀H₄₄N₂O₁₀

Average Mass

592.6860 Da

Monoisotopic Mass

592.29960 Da

IUPAC Name

methyl (2E,4E,8E)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(C-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate

Traditional Name

methyl (2E,4E,8E)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(C-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate

CAS Registry Number

Not Available

SMILES

COC(CC(C)CC1=C(OC)C(=O)C=C(N)C1=O)C(O)C(C)\C=C(/C)C(OC(O)=N)C(OC)\C=C\C=C(/C)C(=O)OC

InChI Identifier

InChI=1S/C30H44N2O10/c1-16(12-20-26(35)21(31)15-22(33)28(20)40-7)13-24(39-6)25(34)18(3)14-19(4)27(42-30(32)37)23(38-5)11-9-10-17(2)29(36)41-8/h9-11,14-16,18,23-25,27,34H,12-13,31H2,1-8H3,(H2,32,37)/b11-9+,17-10+,19-14+

InChI Key

HRKSVRIGRTWRMY-LPCSBIKHSA-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
Streptomyces hygroscopicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

P-benzoquinones

Alternative Parents

Substituents

P-benzoquinone
Fatty acid ester
Fatty acyl
Carbamic acid ester
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous amide
Vinylogous ester
Carboxylic acid ester
Secondary alcohol
Amino acid or derivatives
Carbonic acid derivative
Carboxylic acid derivative
Dialkyl ether
Enamine
Monocarboxylic acid or derivatives
Ether
Hydrocarbon derivative
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organopnictogen compound
Amine
Primary amine
Alcohol
Organic oxide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

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	0.63	ChemAxon
pKa (Strongest Acidic)	-4.6	ChemAxon
pKa (Strongest Basic)	10.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	187.69 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	171.85 m³·mol⁻¹	ChemAxon
Polarizability	62.59 Å³	ChemAxon
Number of Rings	1	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

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4907789

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6392910

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2e,4e,8e)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(c-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate (NP0187096)

MOL for NP0187096 (methyl (2e,4e,8e)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(c-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate)

3D MOL for NP0187096 (methyl (2e,4e,8e)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(c-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate)

3D SDF for NP0187096 (methyl (2e,4e,8e)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(c-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate)

3D-SDF for NP0187096 (methyl (2e,4e,8e)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(c-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate)

PDB for NP0187096 (methyl (2e,4e,8e)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(c-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate)

3D PDB for NP0187096 (methyl (2e,4e,8e)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(c-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate)

SMILES for NP0187096 (methyl (2e,4e,8e)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(c-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate)

INCHI for NP0187096 (methyl (2e,4e,8e)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(c-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate)

Structure for NP0187096 (methyl (2e,4e,8e)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(c-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate)

3D Structure for NP0187096 (methyl (2e,4e,8e)-15-(5-amino-2-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)-11-hydroxy-7-(c-hydroxycarbonimidoyloxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate)