NP-MRD: Showing NP-Card for ({[5-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)acetic acid (NP0240474)

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Record Information

Version

1.0

Created at

2022-09-07 00:18:07 UTC

Updated at

2022-09-07 00:18:08 UTC

NP-MRD ID

NP0240474

Secondary Accession Numbers

None

Natural Product Identification

Common Name

({[5-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)acetic acid

Description

2-({[10-({5-Amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2,5,11,17-tetrahydroxy-19-methoxy-7-methyl-15,22-dioxopentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]Docosa-1(14),2,4(9),5,7,12,16(21),17,19-nonaen-6-yl](hydroxy)methylidene}amino)acetic acid belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4. ({[5-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)acetic acid is found in Actinomadura hibisca. 2-({[10-({5-Amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2,5,11,17-tetrahydroxy-19-methoxy-7-methyl-15,22-dioxopentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]Docosa-1(14),2,4(9),5,7,12,16(21),17,19-nonaen-6-yl](hydroxy)methylidene}amino)acetic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251511082D          

 58 64  0  0  0  0            999 V2000
    4.7250   -2.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5268   -1.9691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1213   -1.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9231   -0.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176   -0.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3195    0.7767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3102   -0.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9047    0.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7066    1.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6974    0.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2918    0.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0845    0.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6789    1.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4808    1.8064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4716    0.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0660    1.3487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8679    2.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0753    2.3784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8771    3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0845    3.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4716    3.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2734    4.5521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2642    3.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8587    4.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6513    3.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8495    3.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6421    2.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2366    3.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0292    3.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0384    4.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6329    4.7809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2458    4.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0476    5.2386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4624    2.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2550    2.4928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6697   -0.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4624   -0.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6605   -1.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4532   -1.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0660   -1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2642   -2.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6697   -2.9987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0568   -2.6555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2550   -3.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0476   -3.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6421   -3.1131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2458   -4.4860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2734   -1.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6789   -1.9691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0753   -0.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2826   -0.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6881   -0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8863   -1.7403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8955   -0.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3010   -1.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4992   -2.0835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5084   -1.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9139   -1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 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
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  1  0  0  0  0
 23 34  1  0  0  0  0
 17 34  1  0  0  0  0
 34 35  1  0  0  0  0
 15 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 40 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
 36 50  1  0  0  0  0
 50 51  1  0  0  0  0
 12 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  2  0  0  0  0
 10 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 55 57  1  0  0  0  0
  7 57  1  0  0  0  0
 57 58  2  0  0  0  0
  3 58  1  0  0  0  0
M  END

     RDKit          3D

 98104  0  0  0  0  0  0  0  0999 V2000
    9.0646   -5.1275    0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1665   -5.7325   -0.8777 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9912   -5.1392   -1.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1576   -5.7747   -2.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9687   -5.1396   -2.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1893   -5.8078   -3.4197 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6573   -3.9112   -2.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5194   -3.2804   -1.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6672   -3.9007   -0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1443   -1.9532   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9652   -1.4549    0.1751 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180   -1.2695   -1.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0759   -1.8998   -1.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9079   -1.2993   -2.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5723   -0.0739   -1.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4148    0.5706   -0.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875   -0.0093   -0.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4499    0.5256    0.3763 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9462    1.8053   -0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6708    2.2208   -0.5980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2418    3.4326   -0.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0206    4.2553    0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4432    5.5599    1.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825    3.8446    0.9828 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1312    4.6361    1.8348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2877    4.1432    2.1664 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9604    5.9046    2.4144 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0613    6.4589    3.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3032    6.6140    2.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3064    6.3439    1.2797 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4953    7.0476    3.0665 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7669    2.5805    0.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9947    2.2470    0.8749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3175    1.4379   -1.3539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1387    0.7658   -0.4478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4684    1.1329   -0.4824 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8452    1.5554    0.7868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6034    0.5911    1.7569 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9788    1.0803    3.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2113   -0.7471    1.4237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1142   -1.6388    1.0438 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1278   -0.5340    0.2570 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9198   -1.5986   -0.0937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2604   -1.3819   -0.0268 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8005   -1.6143   -1.3138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0841   -1.0159   -1.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9853   -1.8647   -0.3830 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.9866   -2.4132   -1.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1651   -2.9792    0.2277 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8965   -3.6273    1.2144 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1554   -1.8364    2.1023 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.8436   -5.8559    0.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4159   -6.7448   -2.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3409   -5.6741   -3.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3490   -3.4344   -0.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2618   -1.8243   -2.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167    0.2659    0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7653    3.8114   -0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2761    5.6014    2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351    6.4036    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6181    5.6104    0.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1858    6.5498    2.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1498    5.6850    4.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7220    7.3731    3.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8534    7.9950    2.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7590    2.5917    1.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9644    2.1435   -1.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004251511082D          

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M  END
> <DATABASE_ID>
NP0240474

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C3=CC4=C(C(O)=C3C(=O)C2=C1)C1=C(O)C(C(=O)NCC(O)=O)=C(C)C=C1C(OC1OC(C)C(N)C(OC2OCC(O)C(O)C2O)C1O)C4O

> <INCHI_IDENTIFIER>
InChI=1S/C38H40N2O18/c1-10-4-16-23(30(49)20(10)36(53)40-8-19(43)44)22-14(7-15-24(31(22)50)27(46)13-5-12(54-3)6-17(41)21(13)26(15)45)28(47)34(16)57-38-33(52)35(25(39)11(2)56-38)58-37-32(51)29(48)18(42)9-55-37/h4-7,11,18,25,28-29,32-35,37-38,41-42,47-52H,8-9,39H2,1-3H3,(H,40,53)(H,43,44)

> <INCHI_KEY>
HELMFNXPQUQJFY-UHFFFAOYSA-N

> <FORMULA>
C38H40N2O18

> <MOLECULAR_WEIGHT>
812.734

> <EXACT_MASS>
812.227612456

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
79.68717162029246

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[10-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2,5,11,17-tetrahydroxy-19-methoxy-7-methyl-15,22-dioxopentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1,3(12),4,6,8,13,16,18,20-nonaen-6-yl]formamido}acetic acid

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
-1.31266154619197

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.006984687975957

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.698114573500166

> <JCHEM_PKA_STRONGEST_BASIC>
8.905818962934926

> <JCHEM_POLAR_SURFACE_AREA>
334.55

> <JCHEM_REFRACTIVITY>
193.77510000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[10-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2,5,11,17-tetrahydroxy-19-methoxy-7-methyl-15,22-dioxopentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1,3(12),4,6,8,13,16,18,20-nonaen-6-yl]formamido}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       8.820  -5.171   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.450  -3.676   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.560  -2.608   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.190  -1.113   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.300  -0.045   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.930   1.450   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      11.779  -0.472   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.889   0.596   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.519   2.091   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.368   0.168   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.478   1.236   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.958   0.809   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.067   1.877   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      17.697   3.372   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      19.547   1.450   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      20.657   2.518   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      20.287   4.013   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      18.807   4.440   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      18.437   5.935   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.958   6.362   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.547   7.002   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      19.177   8.497   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      21.027   6.575   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      22.136   7.643   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      23.616   7.216   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      23.986   5.721   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      25.465   5.294   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.575   6.362   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      28.055   5.935   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      26.205   7.857   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      27.315   8.924   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      24.725   8.284   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      24.356   9.779   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      21.396   5.080   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      22.876   4.653   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      19.917  -0.045   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      21.396  -0.472   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      21.766  -1.967   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      23.246  -2.394   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      20.657  -3.035   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      21.027  -4.530   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      19.917  -5.598   0.000  0.00  0.00           O+0
HETATM   43  N   UNK     0      22.506  -4.957   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      22.876  -6.452   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      24.356  -6.879   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      25.465  -5.811   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      24.725  -8.374   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      19.177  -2.608   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      18.067  -3.676   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      18.807  -1.113   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      17.328  -0.686   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      16.218  -1.754   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      16.588  -3.248   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      14.738  -1.326   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      13.629  -2.394   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      13.998  -3.889   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      12.149  -1.967   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      11.039  -3.035   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   58                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   57                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   54                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   51                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   36                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   34                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   34                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   25   33                                                  
CONECT   33   32                                                            
CONECT   34   23   17   35                                                  
CONECT   35   34                                                            
CONECT   36   15   37   50                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   48                                                  
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   40   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   36   51                                                  
CONECT   51   50   12   52                                                  
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   10   55                                                  
CONECT   55   54   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55    7   58                                                  
CONECT   58   57    3                                                       
MASTER        0    0    0    0    0    0    0    0   58    0  128    0
END

View in JSmol

Synonyms

Value	Source
2-({[10-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2,5,11,17-tetrahydroxy-19-methoxy-7-methyl-15,22-dioxopentacyclo[12.8.0.0,.0,.0,]docosa-1(14),2,4(9),5,7,12,16(21),17,19-nonaen-6-yl](hydroxy)methylidene}amino)acetate	Generator
2-({[10-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2,5,11,17-tetrahydroxy-19-methoxy-7-methyl-15,22-dioxopentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),2,4(9),5,7,12,16(21),17,19-nonaen-6-yl](hydroxy)methylidene}amino)acetate	Generator

Chemical Formula

C₃₈H₄₀N₂O₁₈

Average Mass

812.7340 Da

Monoisotopic Mass

812.22761 Da

IUPAC Name

2-{[10-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2,5,11,17-tetrahydroxy-19-methoxy-7-methyl-15,22-dioxopentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1,3(12),4,6,8,13,16,18,20-nonaen-6-yl]formamido}acetic acid

Traditional Name

{[10-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-2,5,11,17-tetrahydroxy-19-methoxy-7-methyl-15,22-dioxopentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1,3(12),4,6,8,13,16,18,20-nonaen-6-yl]formamido}acetic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C3=CC4=C(C(O)=C3C(=O)C2=C1)C1=C(O)C(C(=O)NCC(O)=O)=C(C)C=C1C(OC1OC(C)C(N)C(OC2OCC(O)C(O)C2O)C1O)C4O

InChI Identifier

InChI=1S/C38H40N2O18/c1-10-4-16-23(30(49)20(10)36(53)40-8-19(43)44)22-14(7-15-24(31(22)50)27(46)13-5-12(54-3)6-17(41)21(13)26(15)45)28(47)34(16)57-38-33(52)35(25(39)11(2)56-38)58-37-32(51)29(48)18(42)9-55-37/h4-7,11,18,25,28-29,32-35,37-38,41-42,47-52H,8-9,39H2,1-3H3,(H,40,53)(H,43,44)

InChI Key

HELMFNXPQUQJFY-UHFFFAOYSA-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
Actinomadura hibisca	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Aminoglycoside core
Tetracenequinone
9,10-anthraquinone
1,4-anthraquinone
Anthracene
Phenanthrene
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
2-naphthalenecarboxamide
2-naphthalenecarboxylic acid or derivatives
Disaccharide
Glycosyl compound
1-naphthol
O-glycosyl compound
Alpha-amino acid or derivatives
Salicylic acid or derivatives
Aryl ketone
Anisole
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Amino saccharide
Oxane
Vinylogous acid
Amino acid
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Ketone
Amino acid or derivatives
Oxacycle
Carboxylic acid
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Ether
Organoheterocyclic compound
Polyol
Organic oxide
Carbonyl group
Organic oxygen compound
Primary aliphatic amine
Alcohol
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Amine
Organopnictogen compound
Primary amine
Hydrocarbon derivative
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	0.7	ALOGPS
logP	-1.3	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	2.7	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	334.55 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	193.78 m³·mol⁻¹	ChemAxon
Polarizability	79.69 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72460

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ({[5-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)acetic acid (NP0240474)

MOL for NP0240474 (({[5-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)acetic acid)

3D MOL for NP0240474 (({[5-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)acetic acid)

3D SDF for NP0240474 (({[5-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)acetic acid)

3D-SDF for NP0240474 (({[5-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)acetic acid)

PDB for NP0240474 (({[5-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)acetic acid)

3D PDB for NP0240474 (({[5-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)acetic acid)

SMILES for NP0240474 (({[5-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)acetic acid)

INCHI for NP0240474 (({[5-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)acetic acid)

Structure for NP0240474 (({[5-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)acetic acid)

3D Structure for NP0240474 (({[5-({5-amino-3-hydroxy-6-methyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5h,6h-naphtho[1,2-b]anthracen-2-yl](hydroxy)methylidene}amino)acetic acid)