NP-MRD: Showing NP-Card for Ansalactam A (NP0009728)

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Record Information

Version

2.0

Created at

2021-01-05 19:18:15 UTC

Updated at

2024-09-12 19:50:51 UTC

NP-MRD ID

NP0009728

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ansalactam A

Provided By

NPAtlas

Description

Ansalactam A belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Ansalactam A is found in Streptomyces sp. Ansalactam A was first documented in 2011 (PMID: 21247149). Based on a literature review a small amount of articles have been published on Ansalactam A (PMID: 27120128) (PMID: 34846908) (PMID: 23654255).

Structure

MOL SDF PDB SMILES InChI

NP0009728
  Mrv2104 05272322233D          

 79 82  0  0  0  0            999 V2000
    3.2106   -2.0145    0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295   -1.1643   -0.3191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1992   -1.4826   -1.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334   -2.5461   -2.0944 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7108   -3.9795   -1.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8505   -2.1203   -1.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0999   -2.7444   -0.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1544   -4.1670   -0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2452   -1.8735   -0.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3508   -2.0759   -0.9573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9406   -0.8230    0.6177 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6142   -1.5844    1.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9830    0.2931    0.9349 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3468    0.3415    0.1818 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3756   -0.6548    0.7477 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3907   -1.2036   -0.2811 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2755   -0.1281   -0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8704    2.2874    0.2729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6912    2.5006    0.9127 N   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4474    1.7598    0.8225 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5195    2.1576    1.9671 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9166    1.8422    1.6397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5898    1.1091    2.3463 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4428    2.4735    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5266    2.6974   -0.6154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9179    3.3875   -1.7732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2326    3.8516   -1.9302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6030    4.5863   -3.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690    3.5484   -0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4911    3.8629   -1.0865 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7862    2.8419    0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3449    3.1230    1.9557 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155    0.8851    1.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547    0.3125    2.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8997    0.2356   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8426    2.1207   -0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500    1.9770   -1.6125 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5489   -2.8492    0.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1280   -2.4391    1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7402   -4.1004   -2.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6394   -1.0845   -1.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0350   -4.8478   -1.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8422   -1.6937   -1.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8102    0.4440   -0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0237   -0.5780   -1.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6854    0.5640   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9696   -2.7036   -0.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6580   -3.0816    0.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8537   -1.8405    1.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7856    3.5105    0.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7945    1.6617    2.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5752    3.2360    2.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1879    3.5544   -2.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0446    5.5577   -2.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7275    4.7756   -3.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3159    3.9966   -3.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6303    4.4521   -1.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985   -0.6750    2.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5591    0.9439    2.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9758    0.2392    3.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928    0.8467   -0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
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 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
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 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
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 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 27 39  1  0  0  0  0
 39 40  2  0  0  0  0
 38  2  1  0  0  0  0
 22 13  1  0  0  0  0
 33 26  1  0  0  0  0
 39 22  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
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  3 44  1  0  0  0  0
  4 45  1  6  0  0  0
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 37 78  1  0  0  0  0
 38 79  1  0  0  0  0
M  END

NP0009728
  Mrv2104 05272322233D          

 79 82  0  0  0  0            999 V2000
    3.2106   -2.0145    0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295   -1.1643   -0.3191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1992   -1.4826   -1.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334   -2.5461   -2.0944 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7108   -3.9795   -1.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8505   -2.1203   -1.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0999   -2.7444   -0.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1544   -4.1670   -0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2452   -1.8735   -0.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3508   -2.0759   -0.9573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9406   -0.8230    0.6177 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6142   -1.5844    1.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9830    0.2931    0.9349 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3468    0.3415    0.1818 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3756   -0.6548    0.7477 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3907   -1.2036   -0.2811 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.4474    1.7598    0.8225 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.7945    1.6617    2.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1879    3.5544   -2.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0446    5.5577   -2.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7275    4.7756   -3.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3159    3.9966   -3.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6303    4.4521   -1.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985   -0.6750    2.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5591    0.9439    2.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9758    0.2392    3.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928    0.8467   -0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 27 39  1  0  0  0  0
 39 40  2  0  0  0  0
 38  2  1  0  0  0  0
 22 13  1  0  0  0  0
 33 26  1  0  0  0  0
 39 22  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
  1 43  1  0  0  0  0
  3 44  1  0  0  0  0
  4 45  1  6  0  0  0
  5 46  1  0  0  0  0
  5 47  1  0  0  0  0
  5 48  1  0  0  0  0
  6 49  1  0  0  0  0
  8 50  1  0  0  0  0
  8 51  1  0  0  0  0
  8 52  1  0  0  0  0
 11 53  1  6  0  0  0
 12 54  1  0  0  0  0
 12 55  1  0  0  0  0
 12 56  1  0  0  0  0
 13 57  1  1  0  0  0
 14 58  1  6  0  0  0
 15 59  1  0  0  0  0
 15 60  1  0  0  0  0
 16 61  1  0  0  0  0
 17 62  1  0  0  0  0
 17 63  1  0  0  0  0
 17 64  1  0  0  0  0
 18 65  1  0  0  0  0
 18 66  1  0  0  0  0
 18 67  1  0  0  0  0
 21 68  1  0  0  0  0
 23 69  1  0  0  0  0
 23 70  1  0  0  0  0
 28 71  1  0  0  0  0
 30 72  1  0  0  0  0
 30 73  1  0  0  0  0
 30 74  1  0  0  0  0
 32 75  1  0  0  0  0
 37 76  1  0  0  0  0
 37 77  1  0  0  0  0
 37 78  1  0  0  0  0
 38 79  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0009728

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C3=C(C([H])=C1C([H])([H])[H])C(=O)[C@]1(N([H])C(=O)[C@]([H])(C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]1([H])[C@]([H])(C(=O)\C(=C([H])\[C@@]([H])(\C([H])=C(\C(\[H])=C(\C2=O)C([H])([H])[H])/C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])C3=O

> <INCHI_IDENTIFIER>
InChI=1/C33H39NO6/c1-15(2)9-23-27-21(8)28(36)18(5)11-16(3)10-17(4)12-19(6)29(37)26-25-22(13-20(7)30(26)38)31(39)33(27,14-24(25)35)34-32(23)40/h10-13,15-16,21,23,27,38H,9,14H2,1-8H3,(H,34,40)/b17-10+,18-11+,19-12+/t16-,21-,23-,27-,33+/s2

> <INCHI_KEY>
DQIBALILJIXVPY-MGFMAQIJNA-N

> <FORMULA>
C33H39NO6

> <MOLECULAR_WEIGHT>
545.676

> <EXACT_MASS>
545.27773798

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
59.30605438067606

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,5R,6R,8E,10R,11E,13E)-17-hydroxy-6,8,10,12,14,18-hexamethyl-4-(2-methylpropyl)-2-azatetracyclo[18.3.1.0^{1,5}.0^{16,21}]tetracosa-8,11,13,16,18,20-hexaene-3,7,15,22,24-pentone

> <JCHEM_LOGP>
6.161332829666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.043128730534752

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.339080619916973

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6395082168048613

> <JCHEM_POLAR_SURFACE_AREA>
117.60999999999999

> <JCHEM_REFRACTIVITY>
157.12889999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,5R,6R,8E,10R,11E,13E)-17-hydroxy-6,8,10,12,14,18-hexamethyl-4-(2-methylpropyl)-2-azatetracyclo[18.3.1.0^{1,5}.0^{16,21}]tetracosa-8,11,13,16,18,20-hexaene-3,7,15,22,24-pentone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: NP0009728                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0       3.211  -2.014   0.881  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.530  -1.164  -0.319  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.199  -1.483  -1.594  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.233  -2.546  -2.094  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.711  -3.979  -1.875  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.851  -2.120  -1.633  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.100  -2.744  -0.916  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.154  -4.167  -0.471  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.245  -1.874  -0.474  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.351  -2.076  -0.957  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.941  -0.823   0.618  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.614  -1.584   1.916  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.983   0.293   0.935  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.347   0.342   0.182  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.376  -0.655   0.748  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.391  -1.204  -0.281  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.276  -0.128  -0.906  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.269  -2.267   0.386  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.775   1.783   0.445  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.870   2.287   0.273  0.00  0.00           O+0
HETATM   21  N   UNK     0      -2.691   2.501   0.913  0.00  0.00           N+0
HETATM   22  C   UNK     0      -1.447   1.760   0.823  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.520   2.158   1.967  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.917   1.842   1.640  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.590   1.109   2.346  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.443   2.474   0.411  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.527   2.697  -0.615  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.918   3.388  -1.773  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.233   3.852  -1.930  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.603   4.586  -3.188  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.169   3.548  -0.932  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.491   3.863  -1.087  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.786   2.842   0.225  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.859   2.357   1.133  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.345   3.123   1.956  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.215   0.885   1.052  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.755   0.313   2.326  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.900   0.236  -0.088  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.843   2.121  -0.555  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.450   1.977  -1.613  0.00  0.00           O+0
HETATM   41  H   UNK     0       2.549  -2.849   0.655  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.128  -2.439   1.299  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.696  -1.440   1.658  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.455  -0.777  -2.387  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.208  -2.427  -3.188  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.740  -4.100  -2.232  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.090  -4.680  -2.444  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.691  -4.295  -0.830  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.639  -1.085  -1.916  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.035  -4.848  -1.305  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.143  -4.422  -0.074  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.574  -4.356   0.323  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.016  -0.331   0.301  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.355  -0.898   2.728  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.467  -2.195   2.238  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.238  -2.258   1.786  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.263   0.169   1.995  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.209   0.227  -0.898  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.843  -1.515   1.174  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.924  -0.198   1.583  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.842  -1.694  -1.093  0.00  0.00           H+0
HETATM   62  H   UNK     0      -6.810   0.444  -0.141  0.00  0.00           H+0
HETATM   63  H   UNK     0      -7.024  -0.578  -1.569  0.00  0.00           H+0
HETATM   64  H   UNK     0      -5.685   0.564  -1.514  0.00  0.00           H+0
HETATM   65  H   UNK     0      -6.970  -2.704  -0.335  0.00  0.00           H+0
HETATM   66  H   UNK     0      -5.658  -3.082   0.789  0.00  0.00           H+0
HETATM   67  H   UNK     0      -6.854  -1.841   1.208  0.00  0.00           H+0
HETATM   68  H   UNK     0      -2.786   3.510   0.910  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.795   1.662   2.906  0.00  0.00           H+0
HETATM   70  H   UNK     0      -0.575   3.236   2.171  0.00  0.00           H+0
HETATM   71  H   UNK     0       0.188   3.554  -2.567  0.00  0.00           H+0
HETATM   72  H   UNK     0       3.045   5.558  -2.944  0.00  0.00           H+0
HETATM   73  H   UNK     0       1.728   4.776  -3.818  0.00  0.00           H+0
HETATM   74  H   UNK     0       3.316   3.997  -3.773  0.00  0.00           H+0
HETATM   75  H   UNK     0       4.630   4.452  -1.845  0.00  0.00           H+0
HETATM   76  H   UNK     0       5.199  -0.675   2.178  0.00  0.00           H+0
HETATM   77  H   UNK     0       5.559   0.944   2.718  0.00  0.00           H+0
HETATM   78  H   UNK     0       3.976   0.239   3.090  0.00  0.00           H+0
HETATM   79  H   UNK     0       3.693   0.847  -0.966  0.00  0.00           H+0
CONECT    1    2   41   42   43                                             
CONECT    2    1    3   38                                                  
CONECT    3    2    4   44                                                  
CONECT    4    3    5    6   45                                             
CONECT    5    4   46   47   48                                             
CONECT    6    4    7   49                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   50   51   52                                             
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   53                                             
CONECT   12   11   54   55   56                                             
CONECT   13   11   14   22   57                                             
CONECT   14   13   15   19   58                                             
CONECT   15   14   16   59   60                                             
CONECT   16   15   17   18   61                                             
CONECT   17   16   62   63   64                                             
CONECT   18   16   65   66   67                                             
CONECT   19   14   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   68                                                  
CONECT   22   21   23   13   39                                             
CONECT   23   22   24   69   70                                             
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   33                                                  
CONECT   27   26   28   39                                                  
CONECT   28   27   29   71                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   72   73   74                                             
CONECT   31   29   32   33                                                  
CONECT   32   31   75                                                       
CONECT   33   31   34   26                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36   76   77   78                                             
CONECT   38   36    2   79                                                  
CONECT   39   27   40   22                                                  
CONECT   40   39                                                            
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    3                                                            
CONECT   45    4                                                            
CONECT   46    5                                                            
CONECT   47    5                                                            
CONECT   48    5                                                            
CONECT   49    6                                                            
CONECT   50    8                                                            
CONECT   51    8                                                            
CONECT   52    8                                                            
CONECT   53   11                                                            
CONECT   54   12                                                            
CONECT   55   12                                                            
CONECT   56   12                                                            
CONECT   57   13                                                            
CONECT   58   14                                                            
CONECT   59   15                                                            
CONECT   60   15                                                            
CONECT   61   16                                                            
CONECT   62   17                                                            
CONECT   63   17                                                            
CONECT   64   17                                                            
CONECT   65   18                                                            
CONECT   66   18                                                            
CONECT   67   18                                                            
CONECT   68   21                                                            
CONECT   69   23                                                            
CONECT   70   23                                                            
CONECT   71   28                                                            
CONECT   72   30                                                            
CONECT   73   30                                                            
CONECT   74   30                                                            
CONECT   75   32                                                            
CONECT   76   37                                                            
CONECT   77   37                                                            
CONECT   78   37                                                            
CONECT   79   38                                                            
MASTER        0    0    0    0    0    0    0    0   79    0  164    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₉NO₆

Average Mass

545.6760 Da

Monoisotopic Mass

545.27774 Da

IUPAC Name

(1S,4R,5R,6R,8E,10R,11E,13E)-17-hydroxy-6,8,10,12,14,18-hexamethyl-4-(2-methylpropyl)-2-azatetracyclo[18.3.1.0^{1,5}.0^{16,21}]tetracosa-8,11,13,16,18,20-hexaene-3,7,15,22,24-pentone

Traditional Name

(1S,4R,5R,6R,8E,10R,11E,13E)-17-hydroxy-6,8,10,12,14,18-hexamethyl-4-(2-methylpropyl)-2-azatetracyclo[18.3.1.0^{1,5}.0^{16,21}]tetracosa-8,11,13,16,18,20-hexaene-3,7,15,22,24-pentone

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C3=C(C([H])=C1C([H])([H])[H])C(=O)[C@]1(N([H])C(=O)[C@]([H])(C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]1([H])[C@]([H])(C(=O)\C(=C([H])\[C@@]([H])(\C([H])=C(\C(\[H])=C(\C2=O)C([H])([H])[H])/C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])C3=O

InChI Identifier

InChI=1/C33H39NO6/c1-15(2)9-23-27-21(8)28(36)18(5)11-16(3)10-17(4)12-19(6)29(37)26-25-22(13-20(7)30(26)38)31(39)33(27,14-24(25)35)34-32(23)40/h10-13,15-16,21,23,27,38H,9,14H2,1-8H3,(H,34,40)/b17-10+,18-11+,19-12+/t16-,21-,23-,27-,33+/s2

InChI Key

DQIBALILJIXVPY-MGFMAQIJNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces sp.	NPAtlas	21247149

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as naphthoquinones. These are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Tetralin
Aryl alkyl ketone
Aryl ketone
Quinone
Vinylogous acid
Cyclic carboximidic acid
Pyrroline
Cyclic ketone
Ketone
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	6.16	ChemAxon
pKa (Strongest Acidic)	7.34	ChemAxon
pKa (Strongest Basic)	-0.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	117.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	157.13 m³·mol⁻¹	ChemAxon
Polarizability	59.31 Å³	ChemAxon
Number of Rings	4	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

NPAtlas ID

NPA016410

HMDB ID

Not Available

DrugBank ID

Not Available

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

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wilson MC, Nam SJ, Gulder TA, Kauffman CA, Jensen PR, Fenical W, Moore BS: Structure and biosynthesis of the marine streptomycete ansamycin ansalactam A and its distinctive branched chain polyketide extender unit. J Am Chem Soc. 2011 Feb 16;133(6):1971-7. doi: 10.1021/ja109226s. Epub 2011 Jan 19. [PubMed:21247149 ]
Le TC, Yang I, Yoon YJ, Nam SJ, Fenical W: Ansalactams B-D Illustrate Further Biosynthetic Plasticity within the Ansamycin Pathway. Org Lett. 2016 May 6;18(9):2256-9. doi: 10.1021/acs.orglett.6b00892. Epub 2016 Apr 27. [PubMed:27120128 ]
Liang Z, Lin YC, Pierce JG: Stereoselective Synthesis of the Spirocyclic gamma-Lactam Core of the Ansalactams. Org Lett. 2021 Dec 17;23(24):9559-9562. doi: 10.1021/acs.orglett.1c03782. Epub 2021 Nov 30. [PubMed:34846908 ]
Lechner A, Wilson MC, Ban YH, Hwang JY, Yoon YJ, Moore BS: Designed biosynthesis of 36-methyl-FK506 by polyketide precursor pathway engineering. ACS Synth Biol. 2013 Jul 19;2(7):379-83. doi: 10.1021/sb3001062. Epub 2012 Nov 5. [PubMed:23654255 ]

Showing NP-Card for Ansalactam A (NP0009728)

MOL for NP0009728 (Ansalactam A)

3D MOL for NP0009728 (Ansalactam A)

3D SDF for NP0009728 (Ansalactam A)

3D-SDF for NP0009728 (Ansalactam A)

PDB for NP0009728 (Ansalactam A)

3D PDB for NP0009728 (Ansalactam A)

SMILES for NP0009728 (Ansalactam A)

INCHI for NP0009728 (Ansalactam A)

Structure for NP0009728 (Ansalactam A)

3D Structure for NP0009728 (Ansalactam A)