NP-MRD: Showing NP-Card for methyl (1r,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate (NP0325364)

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Record Information

Version

2.0

Created at

2022-09-12 06:04:07 UTC

Updated at

2022-09-12 06:04:07 UTC

NP-MRD ID

NP0325364

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate

Description

Sulfurmycin A, also known as sulphurmycin a, belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage. methyl (1r,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate is found in Streptomyces galilaeus. methyl (1r,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate was first documented in 1992 (PMID: 1337431). Based on a literature review very few articles have been published on Sulfurmycin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122208042D          

 60 66  0  0  1  0            999 V2000
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5403    0.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1530    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9774    1.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4146    2.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3648    0.7674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  6  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 29 28  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 29 36  1  0  0  0  0
 27 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 23 39  1  0  0  0  0
 21 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 15 42  1  0  0  0  0
 13 43  1  0  0  0  0
 43 44  1  0  0  0  0
  5 44  1  0  0  0  0
 44 45  1  6  0  0  0
 44 46  1  1  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  2  0  0  0  0
  9 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 52 58  1  0  0  0  0
 58 59  1  0  0  0  0
  8 59  1  0  0  0  0
 59 60  2  0  0  0  0
M  END

     RDKit          3D

113119  0  0  0  0  0  0  0  0999 V2000
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   -6.6498   -2.6951   -0.5293 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6421   -3.2397    1.4554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3333   -1.9359   -0.0890 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6517   -0.4695   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6661    0.0754    0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0057    1.4022    0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2945    2.2444   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2641    1.7342   -0.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5995    2.6277   -1.7934 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8911   -0.1819   -1.8014 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9114   -0.6449   -0.9250 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3693   -0.5158   -0.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9804    1.2634    0.0691 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856   -1.8658   -0.4419 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5315   -3.0265   -0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2539   -1.1703   -1.5458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5437   -1.4243   -2.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.4549    3.8555    2.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.6969    1.1700    2.1986 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6315    1.4333   -0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1227    2.1380    3.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
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   10.6709    1.9538    1.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3653   -1.3317   -0.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7386   -0.0179   -1.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.9896   -0.1211    0.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
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 56112  1  0
 57113  1  0
M  END


  Mrv1652309122208042D          

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 12 13  1  0  0  0  0
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 34 35  1  6  0  0  0
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 27 37  1  0  0  0  0
 37 38  1  6  0  0  0
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 15 42  1  0  0  0  0
 13 43  1  0  0  0  0
 43 44  1  0  0  0  0
  5 44  1  0  0  0  0
 44 45  1  6  0  0  0
 44 46  1  1  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
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  9 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 52 53  2  0  0  0  0
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 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
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 52 58  1  0  0  0  0
 58 59  1  0  0  0  0
  8 59  1  0  0  0  0
 59 60  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0325364

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1C2=CC3=C(C(O)=C2[C@H](C[C@]1(O)CC(C)=O)O[C@H]1C[C@@H]([C@H](O[C@H]2C[C@H](O)[C@H](O[C@H]4CCC(=O)[C@H](C)O4)[C@H](C)O2)[C@H](C)O1)N(C)C)C(=O)C1=C(O)C=CC=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C43H53NO16/c1-18(45)16-43(53)17-29(34-23(36(43)42(52)54-7)13-24-35(39(34)51)38(50)33-22(37(24)49)9-8-10-27(33)47)58-31-14-25(44(5)6)40(20(3)56-31)60-32-15-28(48)41(21(4)57-32)59-30-12-11-26(46)19(2)55-30/h8-10,13,19-21,25,28-32,36,40-41,47-48,51,53H,11-12,14-17H2,1-7H3/t19-,20-,21-,25-,28-,29-,30-,31-,32-,36-,40+,41+,43+/m0/s1

> <INCHI_KEY>
BJOHUNBAORBLAE-KAIPXQOPSA-N

> <FORMULA>
C43H53NO16

> <MOLECULAR_WEIGHT>
839.888

> <EXACT_MASS>
839.336434631

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
113

> <JCHEM_AVERAGE_POLARIZABILITY>
87.30301476190616

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,2S,4S)-4-{[(2R,4S,5S,6S)-4-(dimethylamino)-5-{[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-{[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

> <JCHEM_LOGP>
3.4154724214428636

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.420973102701097

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.8095359690803186

> <JCHEM_PKA_STRONGEST_BASIC>
7.278950207668994

> <JCHEM_POLAR_SURFACE_AREA>
234.11999999999998

> <JCHEM_REFRACTIVITY>
208.9283

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,4S)-4-{[(2R,4S,5S,6S)-4-(dimethylamino)-5-{[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-{[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1H-tetracene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      14.670  -2.310   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      17.338 -10.010   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.670 -11.550   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.336 -14.630   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      12.208   1.594   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      11.486   2.846   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      13.025   2.792   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      13.841   4.098   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      13.748   1.433   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       4.001   3.850   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   44                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   59                                                  
CONECT    9    8   10   50                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6   13                                                  
CONECT   13   12   14   43                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   42                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17   22   40                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   39                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   37                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29                                                       
CONECT   37   27   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   23                                                       
CONECT   40   21   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   15                                                       
CONECT   43   13   44                                                       
CONECT   44   43    5   45   46                                             
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50    9   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   58                                                  
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   52   59                                                  
CONECT   59   58    8   60                                                  
CONECT   60   59                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  132    0
END

View in JSmol

Synonyms

Value	Source
Sulphurmycin a	Generator

Chemical Formula

C₄₃H₅₃NO₁₆

Average Mass

839.8880 Da

Monoisotopic Mass

839.33643 Da

IUPAC Name

methyl (1R,2S,4S)-4-{[(2R,4S,5S,6S)-4-(dimethylamino)-5-{[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-{[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1C2=CC3=C(C(O)=C2[C@H](C[C@]1(O)CC(C)=O)O[C@H]1C[C@@H]([C@H](O[C@H]2C[C@H](O)[C@H](O[C@H]4CCC(=O)[C@H](C)O4)[C@H](C)O2)[C@H](C)O1)N(C)C)C(=O)C1=C(O)C=CC=C1C3=O

InChI Identifier

InChI=1S/C43H53NO16/c1-18(45)16-43(53)17-29(34-23(36(43)42(52)54-7)13-24-35(39(34)51)38(50)33-22(37(24)49)9-8-10-27(33)47)58-31-14-25(44(5)6)40(20(3)56-31)60-32-15-28(48)41(21(4)57-32)59-30-12-11-26(46)19(2)55-30/h8-10,13,19-21,25,28-32,36,40-41,47-48,51,53H,11-12,14-17H2,1-7H3/t19-,20-,21-,25-,28-,29-,30-,31-,32-,36-,40+,41+,43+/m0/s1

InChI Key

BJOHUNBAORBLAE-KAIPXQOPSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces galilaeus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Anthracyclines

Sub Class

Not Available

Direct Parent

Anthracyclines

Alternative Parents

Substituents

Anthracycline
Anthracyclinone-skeleton
Aminoglycoside core
Tetracenequinone
Anthracene carboxylic acid
Anthracene carboxylic acid or derivatives
1,4-anthraquinone
9,10-anthraquinone
Anthracene
1-naphthalenecarboxylic acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Tetralin
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Amino saccharide
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Beta-hydroxy ketone
Oxane
Vinylogous acid
Methyl ester
Tertiary alcohol
Amino acid or derivatives
Cyclic ketone
Tertiary aliphatic amine
Carboxylic acid ester
Tertiary amine
Secondary alcohol
Ketone
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Acetal
Oxacycle
Organoheterocyclic compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aldehyde
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Amine
Organooxygen compound
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	3.42	ChemAxon
pKa (Strongest Acidic)	7.81	ChemAxon
pKa (Strongest Basic)	7.28	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	234.12 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	208.93 m³·mol⁻¹	ChemAxon
Polarizability	87.3 Å³	ChemAxon
Number of Rings	7	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

C00018333

Chemspider ID

137267

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155836

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Coley HM, Twentyman PR, Workman P: Further examination of 9-alkyl- and sugar-modified anthracyclines in the circumvention of multidrug resistance. Anticancer Drug Des. 1992 Dec;7(6):471-81. [PubMed:1337431 ]
LOTUS database [Link]

Showing NP-Card for methyl (1r,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate (NP0325364)

MOL for NP0325364 (methyl (1r,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

3D MOL for NP0325364 (methyl (1r,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

3D SDF for NP0325364 (methyl (1r,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

3D-SDF for NP0325364 (methyl (1r,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

PDB for NP0325364 (methyl (1r,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

3D PDB for NP0325364 (methyl (1r,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

SMILES for NP0325364 (methyl (1r,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

INCHI for NP0325364 (methyl (1r,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

Structure for NP0325364 (methyl (1r,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

3D Structure for NP0325364 (methyl (1r,2s,4s)-4-{[(2r,4s,5s,6s)-4-(dimethylamino)-5-{[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-{[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)