NP-MRD: Showing NP-Card for Macrocidin B (NP0005018)

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Record Information

Version

2.0

Created at

2020-12-09 02:23:07 UTC

Updated at

2021-07-15 16:50:49 UTC

NP-MRD ID

NP0005018

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Macrocidin B

Provided By

NPAtlas

Description

(3S,8R,12S,14S)-5,7,9-trihydroxy-8-methyl-13,16-dioxa-4-azatetracyclo[15.2.2.1³,⁶.0¹²,¹⁴]Docosa-1(19),4,6,17,20-pentaen-22-one belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group. Macrocidin B is found in Didymella macrostoma and Phoma. Based on a literature review very few articles have been published on (3S,8R,12S,14S)-5,7,9-trihydroxy-8-methyl-13,16-dioxa-4-azatetracyclo[15.2.2.1³,⁶.0¹²,¹⁴]Docosa-1(19),4,6,17,20-pentaen-22-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118163D          

 50 53  0  0  0  0            999 V2000
   -3.9936   -1.1365    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5318   -0.6710    0.6756 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9460   -1.3827   -0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144   -1.3686   -1.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7596   -1.9980   -0.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869   -1.9298   -1.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0386   -1.3456   -2.6828 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3381   -2.6606   -1.1645 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0643   -3.3021    0.0669 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2399   -3.0119    0.9908 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3883   -1.5005    1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7644   -0.7752    2.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156    0.6429    2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    1.3244    1.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2825    0.6078    0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1479   -0.8064    0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7965    2.7088    1.2392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9621    3.6717    0.6307 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2318    2.9872   -0.5029 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7216    3.7742   -1.5340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1970    3.4861   -0.5304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1795    2.3792   -0.8366 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2128    1.3496    0.2772 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6072    0.8258    0.3728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3381    0.9894   -0.7999 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3627   -3.1254    1.8669 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7431   -1.1409   -0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5513    4.5449    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5269    0.5145    0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9637    1.8124    1.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1873    1.3035    1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7456    0.9652   -1.5826 H   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  1  0  0  0  0
  3  5  2  0  0  0  0
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  4 32  1  0  0  0  0
  8 33  1  0  0  0  0
  9 34  1  6  0  0  0
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 12 37  1  0  0  0  0
 13 38  1  0  0  0  0
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 16 40  1  0  0  0  0
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 21 44  1  1  0  0  0
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 22 46  1  0  0  0  0
 23 47  1  0  0  0  0
 23 48  1  0  0  0  0
 24 49  1  1  0  0  0
 25 50  1  0  0  0  0
M  END

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
   -3.9936   -1.1365    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5318   -0.6710    0.6756 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9460   -1.3827   -0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144   -1.3686   -1.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7596   -1.9980   -0.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0386   -1.3456   -2.6828 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0643   -3.3021    0.0669 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.6643    1.3244    1.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2825    0.6078    0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1479   -0.8064    0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7965    2.7088    1.2392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9621    3.6717    0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2318    2.9872   -0.5029 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7216    3.7742   -1.5340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1970    3.4861   -0.5304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1795    2.3792   -0.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2128    1.3496    0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242118163D          

 50 53  0  0  0  0            999 V2000
   -3.9936   -1.1365    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5318   -0.6710    0.6756 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9460   -1.3827   -0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144   -1.3686   -1.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7596   -1.9980   -0.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0386   -1.3456   -2.6828 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3381   -2.6606   -1.1645 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0643   -3.3021    0.0669 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2399   -3.0119    0.9908 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3883   -1.5005    1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7644   -0.7752    2.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6643    1.3244    1.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2825    0.6078    0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1479   -0.8064    0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0045   -4.4091   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1436   -3.5806    0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9567    0.9964   -0.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431   -1.1409   -0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5513    4.5449    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5269    0.5145    0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9637    1.8124    1.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1873    1.3035    1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7456    0.9652   -1.5826 H   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  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  2  0  0  0  0
 24  2  1  0  0  0  0
 26  5  1  0  0  0  0
 16 11  1  0  0  0  0
 21 19  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  2 31  1  1  0  0  0
  4 32  1  0  0  0  0
  8 33  1  0  0  0  0
  9 34  1  6  0  0  0
 10 35  1  0  0  0  0
 10 36  1  0  0  0  0
 12 37  1  0  0  0  0
 13 38  1  0  0  0  0
 15 39  1  0  0  0  0
 16 40  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
 19 43  1  6  0  0  0
 21 44  1  1  0  0  0
 22 45  1  0  0  0  0
 22 46  1  0  0  0  0
 23 47  1  0  0  0  0
 23 48  1  0  0  0  0
 24 49  1  1  0  0  0
 25 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005018

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O\C1=C2/C(=O)N([H])[C@]([H])(C2=O)C([H])([H])C2=C([H])C([H])=C(OC([H])([H])[C@]3([H])O[C@@]3([H])C([H])([H])C([H])([H])[C@@]([H])(O[H])[C@@]1([H])C([H])([H])[H])C([H])=C2[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO6/c1-10-14(22)6-7-15-16(27-15)9-26-12-4-2-11(3-5-12)8-13-19(24)17(18(10)23)20(25)21-13/h2-5,10,13-16,22-23H,6-9H2,1H3,(H,21,25)/b18-17-/t10-,13+,14-,15+,16+/m1/s1

> <INCHI_KEY>
VTJGYKOVEXOBKN-VAQVMYBHSA-N

> <FORMULA>
C20H23NO6

> <MOLECULAR_WEIGHT>
373.405

> <EXACT_MASS>
373.152537465

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.74365711519178

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6Z,8R,9R,12S,14S)-7,9-dihydroxy-8-methyl-13,16-dioxa-4-azatetracyclo[15.2.2.1^{3,6}.0^{12,14}]docosa-1(19),6,17,20-tetraene-5,22-dione

> <ALOGPS_LOGP>
0.43

> <JCHEM_LOGP>
0.9761961849999992

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.227478258717472

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.457384158328492

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3261214165425605

> <JCHEM_POLAR_SURFACE_AREA>
108.39000000000001

> <JCHEM_REFRACTIVITY>
96.90109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6Z,8R,9R,12S,14S)-7,9-dihydroxy-8-methyl-13,16-dioxa-4-azatetracyclo[15.2.2.1^{3,6}.0^{12,14}]docosa-1(19),6,17,20-tetraene-5,22-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
   -3.9936   -1.1365    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5318   -0.6710    0.6756 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9460   -1.3827   -0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144   -1.3686   -1.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7596   -1.9980   -0.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869   -1.9298   -1.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0386   -1.3456   -2.6828 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3381   -2.6606   -1.1645 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0643   -3.3021    0.0669 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2399   -3.0119    0.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3883   -1.5005    1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7644   -0.7752    2.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156    0.6429    2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    1.3244    1.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2825    0.6078    0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1479   -0.8064    0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7965    2.7088    1.2392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9621    3.6717    0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2318    2.9872   -0.5029 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7216    3.7742   -1.5340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1970    3.4861   -0.5304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1795    2.3792   -0.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2128    1.3496    0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072    0.8258    0.3728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3381    0.9894   -0.7999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2021   -2.7469    0.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3627   -3.1254    1.8669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4915   -0.7839    1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0149   -2.2244    0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4820   -0.7002   -0.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0392   -0.8624    1.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3040   -2.1510   -1.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325   -2.6876   -1.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0045   -4.4091   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0299   -3.5542    1.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1436   -3.5806    0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0847   -1.0656    2.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3450    1.0548    2.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9567    0.9964   -0.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431   -1.1409   -0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5513    4.5449    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1921    4.0450    1.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4020    1.9145   -0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5163    4.2748    0.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1691    2.8582   -0.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9427    1.8899   -1.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5269    0.5145    0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9637    1.8124    1.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1873    1.3035    1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7456    0.9652   -1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  9 26  1  0
 26 27  2  0
 24  2  1  0
 26  5  1  0
 16 11  1  0
 21 19  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  1
  4 32  1  0
  8 33  1  0
  9 34  1  6
 10 35  1  0
 10 36  1  0
 12 37  1  0
 13 38  1  0
 15 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  6
 21 44  1  1
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  1
 25 50  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.994  -1.137   0.756  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.532  -0.671   0.676  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.946  -1.383  -0.483  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.714  -1.369  -1.664  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.760  -1.998  -0.406  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.187  -1.930  -1.554  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.039  -1.346  -2.683  0.00  0.00           O+0
HETATM    8  N   UNK     0       1.338  -2.661  -1.165  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.064  -3.302   0.067  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.240  -3.012   0.991  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.388  -1.500   1.047  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.764  -0.775   2.030  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.916   0.643   2.077  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.664   1.324   1.173  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.283   0.608   0.198  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.148  -0.806   0.129  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.797   2.709   1.239  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.962   3.672   0.631  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.232   2.987  -0.503  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.722   3.774  -1.534  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.197   3.486  -0.530  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.180   2.379  -0.837  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.213   1.350   0.277  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.607   0.826   0.373  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.338   0.989  -0.800  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.202  -2.747   0.642  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.363  -3.125   1.867  0.00  0.00           O+0
HETATM   28  H   UNK     0      -4.492  -0.784   1.658  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.015  -2.224   0.609  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.482  -0.700  -0.163  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.039  -0.862   1.633  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.304  -2.151  -1.919  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.232  -2.688  -1.746  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.004  -4.409  -0.005  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.030  -3.554   1.908  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.144  -3.581   0.663  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.085  -1.066   2.888  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.345   1.055   2.962  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.957   0.996  -0.627  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.743  -1.141  -0.770  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.551   4.545   0.252  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.192   4.045   1.351  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.402   1.915  -0.711  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.516   4.275   0.176  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.169   2.858  -0.976  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.943   1.890  -1.810  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.527   0.515   0.066  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.964   1.812   1.263  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.187   1.304   1.190  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.746   0.965  -1.583  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    1    3   24   31                                             
CONECT    3    2    4    5                                                  
CONECT    4    3   32                                                       
CONECT    5    3    6   26                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   33                                                  
CONECT    9    8   10   26   34                                             
CONECT   10    9   11   35   36                                             
CONECT   11   10   12   16                                                  
CONECT   12   11   13   37                                                  
CONECT   13   12   14   38                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16   39                                                  
CONECT   16   15   11   40                                                  
CONECT   17   14   18                                                       
CONECT   18   17   19   41   42                                             
CONECT   19   18   20   21   43                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   19   44                                             
CONECT   22   21   23   45   46                                             
CONECT   23   22   24   47   48                                             
CONECT   24   23   25    2   49                                             
CONECT   25   24   50                                                       
CONECT   26    9   27    5                                                  
CONECT   27   26                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    2                                                            
CONECT   32    4                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   10                                                            
CONECT   37   12                                                            
CONECT   38   13                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   18                                                            
CONECT   42   18                                                            
CONECT   43   19                                                            
CONECT   44   21                                                            
CONECT   45   22                                                            
CONECT   46   22                                                            
CONECT   47   23                                                            
CONECT   48   23                                                            
CONECT   49   24                                                            
CONECT   50   25                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  106    0
END

RDKit          3D

50 53  0  0  0  0  0  0  0  0999 V2000
   -3.9936   -1.1365    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5318   -0.6710    0.6756 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9460   -1.3827   -0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144   -1.3686   -1.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7596   -1.9980   -0.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869   -1.9298   -1.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0386   -1.3456   -2.6828 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3381   -2.6606   -1.1645 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0643   -3.3021    0.0669 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2399   -3.0119    0.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3883   -1.5005    1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7644   -0.7752    2.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156    0.6429    2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    1.3244    1.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2825    0.6078    0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1479   -0.8064    0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7965    2.7088    1.2392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9621    3.6717    0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2318    2.9872   -0.5029 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7216    3.7742   -1.5340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1970    3.4861   -0.5304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1795    2.3792   -0.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2128    1.3496    0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072    0.8258    0.3728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3381    0.9894   -0.7999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2021   -2.7469    0.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3627   -3.1254    1.8669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4915   -0.7839    1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0149   -2.2244    0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4820   -0.7002   -0.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0392   -0.8624    1.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3040   -2.1510   -1.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325   -2.6876   -1.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0045   -4.4091   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0299   -3.5542    1.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1436   -3.5806    0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0847   -1.0656    2.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3450    1.0548    2.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9567    0.9964   -0.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431   -1.1409   -0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5513    4.5449    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1921    4.0450    1.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4020    1.9145   -0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5163    4.2748    0.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1691    2.8582   -0.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9427    1.8899   -1.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5269    0.5145    0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9637    1.8124    1.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1873    1.3035    1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7456    0.9652   -1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  9 26  1  0
 26 27  2  0
 24  2  1  0
 26  5  1  0
 16 11  1  0
 21 19  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  1
  4 32  1  0
  8 33  1  0
  9 34  1  6
 10 35  1  0
 10 36  1  0
 12 37  1  0
 13 38  1  0
 15 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  6
 21 44  1  1
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  1
 25 50  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₀H₂₃NO₆

Average Mass

373.4050 Da

Monoisotopic Mass

373.15254 Da

IUPAC Name

(3S,6Z,8R,9R,12S,14S)-7,9-dihydroxy-8-methyl-13,16-dioxa-4-azatetracyclo[15.2.2.1^{3,6}.0^{12,14}]docosa-1(19),6,17,20-tetraene-5,22-dione

Traditional Name

(3S,6Z,8R,9R,12S,14S)-7,9-dihydroxy-8-methyl-13,16-dioxa-4-azatetracyclo[15.2.2.1^{3,6}.0^{12,14}]docosa-1(19),6,17,20-tetraene-5,22-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1C(O)CC[C@@H]2O[C@H]2COC2=CC=C(C[C@@H]3NC(=O)\C(C3=O)=C1/O)C=C2

InChI Identifier

InChI=1S/C20H23NO6/c1-10-14(22)6-7-15-16(27-15)9-26-12-4-2-11(3-5-12)8-13-19(24)17(18(10)23)20(25)21-13/h2-5,10,13-16,22-23H,6-9H2,1H3,(H,21,25)/b18-17-/t10-,13+,14?,15+,16+/m1/s1

InChI Key

VTJGYKOVEXOBKN-VAQVMYBHSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Didymella macrostoma	LOTUS Database	35616633
Phoma	NPAtlas	14695796

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Alkyl aryl ethers

Alternative Parents

Substituents

Alkyl aryl ether
Benzenoid
Vinylogous acid
Cyclic carboximidic acid
Pyrroline
Secondary alcohol
Ketone
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Oxirane
Enol
Dialkyl ether
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Alcohol
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	0.43	ALOGPS
logP	0.98	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	5.46	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.39 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	96.9 m³·mol⁻¹	ChemAxon
Polarizability	36.74 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA009799

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78442627

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585809

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Macrocidin B (NP0005018)

MOL for NP0005018 (Macrocidin B)

3D MOL for NP0005018 (Macrocidin B)

3D SDF for NP0005018 (Macrocidin B)

3D-SDF for NP0005018 (Macrocidin B)

PDB for NP0005018 (Macrocidin B)

3D PDB for NP0005018 (Macrocidin B)

SMILES for NP0005018 (Macrocidin B)

INCHI for NP0005018 (Macrocidin B)

Structure for NP0005018 (Macrocidin B)

3D Structure for NP0005018 (Macrocidin B)