NP-MRD: Showing NP-Card for methyl 9-[(1s)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxotetraphene-10-carboxylate (NP0182855)

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Record Information

Version

2.0

Created at

2022-09-03 21:39:51 UTC

Updated at

2022-09-03 21:39:52 UTC

NP-MRD ID

NP0182855

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 9-[(1s)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxotetraphene-10-carboxylate

Description

Methyl 9-[(1S)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxo-7,12-dihydrotetraphene-10-carboxylate belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone. Based on a literature review very few articles have been published on methyl 9-[(1S)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxo-7,12-dihydrotetraphene-10-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032223392D          

 36 39  0  0  1  0            999 V2000
    2.9366   -3.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4767   -2.8518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2066   -2.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3965   -1.9164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5569   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0970   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0168   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467    0.7341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4767   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666   -0.5132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3965    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1265   -1.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3163   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7762   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0463   -0.2014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3670    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0970    1.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7172    0.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4472    1.6696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274    0.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7974   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6075   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8776   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6877   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3375   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6075   -2.3841    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.5274   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9873   -2.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2573   -2.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2573   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4472   -0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9071   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771   -1.9164    0.0000 O   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
  8 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  2  0  0  0  0
 20 34  1  0  0  0  0
 34 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -3.2787   -5.0807   -1.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5265   -3.9345   -0.8243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0989   -2.6889   -0.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3728   -2.6658   -0.8792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4138   -1.4593   -0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0049   -1.5790   -0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2477   -0.4543   -0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8317    0.7977   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1926    0.9336   -0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8327    2.1218   -0.1310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0005   -0.2387   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4572   -0.0693   -0.3043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7579    0.7187   -1.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7696    1.0741    0.5855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9466    1.1179    1.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1585    2.3709    2.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7211    0.1617    1.2956 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0179    1.9563    0.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    3.0973    0.0867 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4509    1.8197    0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2330    2.9794    0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6065    4.2091    0.1686 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5786    2.8850    0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1869    1.6504   -0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787    1.6046   -0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1910    0.3869   -0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6885    0.3703   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4680   -0.7754   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2282   -2.3275   -0.4409 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0679   -0.7369   -0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5014   -1.9867   -0.1296 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083   -2.7553    1.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4391    0.4485   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0494    0.5575   -0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2329   -0.6241   -0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5947   -1.7739   -0.2308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -5.8467   -1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0929   -4.8341   -1.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8139   -5.4883   -0.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5637   -2.5767   -0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6305    3.0464   -0.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1472   -0.8321   -0.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3874    1.7321   -1.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8431    0.6561   -1.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2120    0.1409   -2.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1308    2.1903    3.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1621    2.8100    1.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4020    3.1370    1.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0998    5.0776    0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1881    3.7736    0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1334    2.5562   -0.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0933    1.2029    0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9279    0.4627   -1.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0541   -0.6428   -0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2851   -2.0433    1.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9308   -3.6135    1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6577   -3.0192    1.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  8 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 31 32  1  0
 30 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 11  5  1  0
 34 20  1  0
 35  7  1  0
 33 24  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  6 40  1  0
 10 41  1  0
 12 42  1  1
 13 43  1  0
 13 44  1  0
 13 45  1  0
 16 46  1  0
 16 47  1  0
 16 48  1  0
 22 49  1  0
 23 50  1  0
 25 51  1  0
 27 52  1  0
 27 53  1  0
 27 54  1  0
 32 55  1  0
 32 56  1  0
 32 57  1  0
M  END


  Mrv1652309032223392D          

 36 39  0  0  1  0            999 V2000
    2.9366   -3.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4767   -2.8518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2066   -2.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3965   -1.9164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5569   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0970   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0168   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467    0.7341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4767   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666   -0.5132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3965    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1265   -1.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3163   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7762   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0463   -0.2014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3670    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0970    1.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7172    0.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4472    1.6696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274    0.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7974   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6075   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8776   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6877   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3375   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6075   -2.3841    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.5274   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9873   -2.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2573   -2.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2573   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4472   -0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9071   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771   -1.9164    0.0000 O   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
  8 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  2  0  0  0  0
 20 34  1  0  0  0  0
 34 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0182855

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC2=C(C(O)=C1[C@H](C)OC(C)=O)C(=O)C1=C(O)C=C3C=C(C)C(Cl)=C(OC)C3=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H21ClO9/c1-9-6-12-7-15(29)19-20(17(12)25(34-4)21(9)27)22(30)13-8-14(26(33)35-5)16(10(2)36-11(3)28)23(31)18(13)24(19)32/h6-8,10,29,31H,1-5H3/t10-/m0/s1

> <INCHI_KEY>
MFLXCCWOEBQIHW-JTQLQIEISA-N

> <FORMULA>
C26H21ClO9

> <MOLECULAR_WEIGHT>
512.9

> <EXACT_MASS>
512.08741

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
51.515189624055054

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 9-[(1S)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxo-7,12-dihydrotetraphene-10-carboxylate

> <JCHEM_LOGP>
5.654674619666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.105159505485613

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.323973604186085

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8992528082918865

> <JCHEM_POLAR_SURFACE_AREA>
136.43

> <JCHEM_REFRACTIVITY>
130.28369999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 9-[(1S)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxotetraphene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       5.482  -6.488   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.490  -5.323   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.986  -3.868   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.473  -3.577   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.994  -2.704   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.506  -2.995   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.514  -1.831   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.010  -0.376   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.498  -0.085   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.994   1.370   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.490  -1.249   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.978  -0.958   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.473   0.497   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.969  -2.122   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.457  -1.831   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.449  -2.995   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.953  -0.376   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.018   0.788   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.514   2.243   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.531   0.497   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.539   1.661   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.035   3.117   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.051   1.370   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.555  -0.085   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.067  -0.376   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.571  -1.831   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.084  -2.122   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.563  -2.995   0.000  0.00  0.00           C+0
HETATM   29 Cl   UNK     0      16.067  -4.450   0.000  0.00  0.00          Cl+0
HETATM   30  C   UNK     0      14.051  -2.704   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.043  -3.868   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.547  -5.323   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.547  -1.249   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.035  -0.958   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.027  -2.122   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.531  -3.577   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   35                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    8   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   34                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   24   34                                                  
CONECT   34   33   20   35                                                  
CONECT   35   34    7   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
Methyl 9-[(1S)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxo-7,12-dihydrotetraphene-10-carboxylic acid	Generator

Chemical Formula

C₂₆H₂₁ClO₉

Average Mass

512.9000 Da

Monoisotopic Mass

512.08741 Da

IUPAC Name

methyl 9-[(1S)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxo-7,12-dihydrotetraphene-10-carboxylate

Traditional Name

methyl 9-[(1S)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxotetraphene-10-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC2=C(C(O)=C1[C@H](C)OC(C)=O)C(=O)C1=C(O)C=C3C=C(C)C(Cl)=C(OC)C3=C1C2=O

InChI Identifier

InChI=1S/C26H21ClO9/c1-9-6-12-7-15(29)19-20(17(12)25(34-4)21(9)27)22(30)13-8-14(26(33)35-5)16(10(2)36-11(3)28)23(31)18(13)24(19)32/h6-8,10,29,31H,1-5H3/t10-/m0/s1

InChI Key

MFLXCCWOEBQIHW-JTQLQIEISA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Angucyclines

Sub Class

Not Available

Direct Parent

Angucyclines

Alternative Parents

Substituents

Angucycline core
Anthracene carboxylic acid or derivatives
Anthracene carboxylic acid
Anthraquinone
9,10-anthraquinone
Phenanthrol
Phenanthrene
Anthracene
2-naphthalenecarboxylic acid or derivatives
2-naphthalenecarboxylic acid
2-naphthol
Chloronaphthalene
Aryl ketone
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Aryl chloride
Aryl halide
Dicarboxylic acid or derivatives
Vinylogous acid
Methyl ester
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Ether
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Organochloride
Organohalogen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	5.65	ChemAxon
pKa (Strongest Acidic)	7.32	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	136.43 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	130.28 m³·mol⁻¹	ChemAxon
Polarizability	51.52 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	Yes	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

57642908

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162922294

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 9-[(1s)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxotetraphene-10-carboxylate (NP0182855)

MOL for NP0182855 (methyl 9-[(1s)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxotetraphene-10-carboxylate)

3D MOL for NP0182855 (methyl 9-[(1s)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxotetraphene-10-carboxylate)

3D SDF for NP0182855 (methyl 9-[(1s)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxotetraphene-10-carboxylate)

3D-SDF for NP0182855 (methyl 9-[(1s)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxotetraphene-10-carboxylate)

PDB for NP0182855 (methyl 9-[(1s)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxotetraphene-10-carboxylate)

3D PDB for NP0182855 (methyl 9-[(1s)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxotetraphene-10-carboxylate)

SMILES for NP0182855 (methyl 9-[(1s)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxotetraphene-10-carboxylate)

INCHI for NP0182855 (methyl 9-[(1s)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxotetraphene-10-carboxylate)

Structure for NP0182855 (methyl 9-[(1s)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxotetraphene-10-carboxylate)

3D Structure for NP0182855 (methyl 9-[(1s)-1-(acetyloxy)ethyl]-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxotetraphene-10-carboxylate)