Np mrd loader

Showing NP-Card for Squarrosanin A (NP0073750)

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Record Information
Version2.0
Created at2022-04-28 18:58:31 UTC
Updated at2022-04-28 18:58:31 UTC
NP-MRD IDNP0073750
Secondary Accession NumbersNone
Natural Product Identification
Common NameSquarrosanin A
Description(10R,11R)-10-[(14R,15S,19R)-2,3,4,7,8,9-hexahydroxy-12,17-dioxo-19-{6,7,12,13-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]Hexadeca-1(15),4,6,8(16),11,13-hexaen-5-yl}-13,16-dioxatetracyclo[13.3.1.0⁵,¹⁸.0⁶,¹¹]Nonadeca-1,3,5(18),6,8,10-hexaen-14-yl]-3,4,5,17,18,19-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.0²,⁷]Nonadeca-1(19),2,4,6,15,17-hexaen-11-yl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Squarrosanin A is found in Melaleuca squarrosa. Based on a literature review very few articles have been published on (10R,11R)-10-[(14R,15S,19R)-2,3,4,7,8,9-hexahydroxy-12,17-dioxo-19-{6,7,12,13-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]Hexadeca-1(15),4,6,8(16),11,13-hexaen-5-yl}-13,16-dioxatetracyclo[13.3.1.0⁵,¹⁸.0⁶,¹¹]Nonadeca-1,3,5(18),6,8,10-hexaen-14-yl]-3,4,5,17,18,19-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.0²,⁷]Nonadeca-1(19),2,4,6,15,17-hexaen-11-yl 3,4,5-trihydroxybenzoate.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0073750 (Squarrosanin A)


  Mrv1652304282220582D          

 88 99  0  0  1  0            999 V2000
    7.7943   -1.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
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3D MOL for NP0073750 (Squarrosanin A)

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3D SDF for NP0073750 (Squarrosanin A)

  Mrv1652304282220582D          

 88 99  0  0  1  0            999 V2000
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   10.8857   -0.6508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5989    1.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6739    1.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4230    2.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0969    1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0219    0.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2728    0.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7392    0.4028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9267    1.9627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1070    2.7406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2693   -0.2444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8568   -0.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0884   -1.7946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6193    1.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7943    1.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3818    1.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7943    2.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6193    2.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0318    1.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7277    2.2266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8351    3.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3818    3.3279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5568    3.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9808    3.9821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1443    2.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5568    1.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1443    1.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5568    0.4700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3818    0.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2226   -0.2268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3193    1.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9068    1.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3193    2.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7437    3.2523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0472    1.8975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4442   -2.5902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 17 23  1  0  0  0  0
 11 24  1  1  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  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 34 36  1  0  0  0  0
 33 37  1  0  0  0  0
 32 38  1  0  0  0  0
 31 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 39 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
 24 47  1  6  0  0  0
 42 48  1  0  0  0  0
 41 49  1  0  0  0  0
 40 50  1  0  0  0  0
 25 51  1  6  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 52 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 54 59  1  0  0  0  0
 58 60  1  0  0  0  0
 57 61  1  0  0  0  0
 56 62  1  0  0  0  0
 10 63  1  1  0  0  0
 63 64  1  0  0  0  0
  3 64  1  0  0  0  0
 64 65  2  0  0  0  0
  9 66  1  6  0  0  0
 66 67  2  0  0  0  0
 67 68  1  0  0  0  0
 68 69  2  0  0  0  0
 69 70  1  0  0  0  0
 70 71  2  0  0  0  0
 66 71  1  0  0  0  0
 71 72  1  0  0  0  0
 70 73  1  0  0  0  0
 69 74  1  0  0  0  0
 74 75  1  0  0  0  0
 75 76  2  0  0  0  0
 75 77  1  0  0  0  0
 77 78  1  0  0  0  0
 68 78  1  0  0  0  0
 78 79  2  0  0  0  0
 79 80  1  0  0  0  0
 80 81  1  0  0  0  0
 67 81  1  0  0  0  0
 81 82  2  0  0  0  0
 79 83  1  0  0  0  0
 83 84  2  0  0  0  0
 84 85  1  0  0  0  0
 77 85  2  0  0  0  0
 85 86  1  0  0  0  0
 84 87  1  0  0  0  0
  1 88  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073750

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1COC(=O)C2=C(C(O)=C(O)C(O)=C2)C2=C(O)C(O)=C(O)C=C2C(=O)O[C@H]1[C@@H]1OC(=O)C2=C(C(O)=C(O)C(O)=C2)C2=C(O)C(O)=C(O)C3=C2C(=O)O[C@H]1[C@H]3C1=C2C(=O)OC3=C4C(C(=O)OC(C(O)=C1O)=C24)=C(O)C(O)=C3

> <INCHI_IDENTIFIER>
InChI=1S/C55H32O33/c56-12-1-8(2-13(57)32(12)62)49(75)84-19-7-82-50(76)9-3-14(58)34(64)37(67)20(9)21-10(4-15(59)35(65)38(21)68)51(77)85-45(19)48-47-28(26-30-27-23-18(83-53(30)79)6-17(61)33(63)31(23)55(81)86-46(27)44(74)42(26)72)25-29(54(80)87-47)24(40(70)43(73)41(25)71)22-11(52(78)88-48)5-16(60)36(66)39(22)69/h1-6,19,28,45,47-48,56-74H,7H2/t19-,28-,45-,47+,48+/m1/s1

> <INCHI_KEY>
NCKJEPQXUIIESS-QVWPFDLFSA-N

> <FORMULA>
C55H32O33

> <MOLECULAR_WEIGHT>
1220.828

> <EXACT_MASS>
1220.08258349

> <JCHEM_ACCEPTOR_COUNT>
26

> <JCHEM_ATOM_COUNT>
120

> <JCHEM_AVERAGE_POLARIZABILITY>
106.53911122477724

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
19

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10R,11R)-10-[(14R,15S,19R)-2,3,4,7,8,9-hexahydroxy-12,17-dioxo-19-{6,7,12,13-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4,6,8(16),11,13-hexaen-5-yl}-13,16-dioxatetracyclo[13.3.1.0^{5,18}.0^{6,11}]nonadeca-1(18),2,4,6(11),7,9-hexaen-14-yl]-3,4,5,17,18,19-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.0^{2,7}]nonadeca-1(15),2,4,6,16,18-hexaen-11-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
5.312403580999999

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
12

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
7.334418104854274

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.606132292991488

> <JCHEM_PKA_STRONGEST_BASIC>
-4.601619254742208

> <JCHEM_POLAR_SURFACE_AREA>
568.4700000000001

> <JCHEM_REFRACTIVITY>
281.517

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10R,11R)-10-[(14R,15S,19R)-2,3,4,7,8,9-hexahydroxy-12,17-dioxo-19-{6,7,12,13-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4,6,8(16),11,13-hexaen-5-yl}-13,16-dioxatetracyclo[13.3.1.0^{5,18}.0^{6,11}]nonadeca-1(18),2,4,6(11),7,9-hexaen-14-yl]-3,4,5,17,18,19-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.0^{2,7}]nonadeca-1(15),2,4,6,16,18-hexaen-11-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0073750 (Squarrosanin A)
Download
PDB for NP0073750 (Squarrosanin A)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      14.549  -3.124   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.089  -3.124   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.859  -1.790   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.089  -0.456   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.103  -0.110   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.779  -1.790   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.500  -2.544   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      14.707   1.383   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      16.859   0.877   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.399   0.877   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.125   1.751   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.594   1.590   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.449   0.560   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.063   1.491   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.129  -0.947   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.756  -2.354   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.850  -3.600   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.319  -3.439   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.692  -2.032   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.598  -0.786   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.991  -2.083   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      11.482  -4.900   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      15.174  -4.779   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      17.504   3.244   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.135   3.667   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.531   3.016   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      21.581   4.143   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      20.834   5.490   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      19.297   5.817   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      21.140   7.147   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.014   8.197   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.360   9.697   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      21.832  10.148   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      22.959   9.098   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      22.613   7.598   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      24.436   9.733   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      22.508  11.613   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      20.159  11.303   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      18.541   7.746   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      18.090   9.218   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      16.590   9.564   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      15.540   8.437   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      15.991   6.965   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      17.491   6.619   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      18.195   6.245   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      19.936   6.718   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      16.377   4.294   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      14.276   9.510   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      15.830  11.005   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      18.061  10.841   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      18.984   2.000   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      20.181   0.641   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      20.320  -1.215   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      21.651   1.890   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      21.791   3.424   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      23.190   4.069   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      24.448   3.181   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      24.307   1.648   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      22.909   1.002   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      25.647   0.752   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      25.996   3.664   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      24.466   5.116   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      19.169  -0.456   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      18.399  -1.790   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      18.832  -3.350   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      16.089   2.211   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      14.549   2.211   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      13.779   3.545   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      14.549   4.878   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      16.089   4.878   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      16.859   3.545   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0      18.158   4.156   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0      16.492   6.215   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      13.779   6.212   0.000  0.00  0.00           O+0
HETATM   75  C   UNK     0      12.239   6.212   0.000  0.00  0.00           C+0
HETATM   76  O   UNK     0      11.164   7.433   0.000  0.00  0.00           O+0
HETATM   77  C   UNK     0      11.469   4.878   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      12.239   3.545   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      11.469   2.211   0.000  0.00  0.00           C+0
HETATM   80  O   UNK     0      12.239   0.877   0.000  0.00  0.00           O+0
HETATM   81  C   UNK     0      13.779   0.877   0.000  0.00  0.00           C+0
HETATM   82  O   UNK     0      13.482  -0.423   0.000  0.00  0.00           O+0
HETATM   83  C   UNK     0       9.929   2.211   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0       9.159   3.545   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0       9.929   4.878   0.000  0.00  0.00           C+0
HETATM   86  O   UNK     0       8.855   6.071   0.000  0.00  0.00           O+0
HETATM   87  O   UNK     0       7.555   3.542   0.000  0.00  0.00           O+0
HETATM   88  O   UNK     0      13.896  -4.835   0.000  0.00  0.00           O+0
CONECT    1    2    6   88                                                  
CONECT    2    1    3   16                                                  
CONECT    3    2    4   64                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    4   10   66                                                  
CONECT   10    9   11   63                                                  
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15    2   17                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   15                                                       
CONECT   21   19                                                            
CONECT   22   18                                                            
CONECT   23   17                                                            
CONECT   24   11   25   47                                                  
CONECT   25   24   26   51                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   35                                                  
CONECT   31   30   32   39                                                  
CONECT   32   31   33   38                                                  
CONECT   33   32   34   37                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34   30                                                       
CONECT   36   34                                                            
CONECT   37   33                                                            
CONECT   38   32                                                            
CONECT   39   31   40   44                                                  
CONECT   40   39   41   50                                                  
CONECT   41   40   42   49                                                  
CONECT   42   41   43   48                                                  
CONECT   43   42   44                                                       
CONECT   44   43   39   45                                                  
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   24                                                       
CONECT   48   42                                                            
CONECT   49   41                                                            
CONECT   50   40                                                            
CONECT   51   25   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55   59                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57   62                                                  
CONECT   57   56   58   61                                                  
CONECT   58   57   59   60                                                  
CONECT   59   58   54                                                       
CONECT   60   58                                                            
CONECT   61   57                                                            
CONECT   62   56                                                            
CONECT   63   10   64                                                       
CONECT   64   63    3   65                                                  
CONECT   65   64                                                            
CONECT   66    9   67   71                                                  
CONECT   67   66   68   81                                                  
CONECT   68   67   69   78                                                  
CONECT   69   68   70   74                                                  
CONECT   70   69   71   73                                                  
CONECT   71   70   66   72                                                  
CONECT   72   71                                                            
CONECT   73   70                                                            
CONECT   74   69   75                                                       
CONECT   75   74   76   77                                                  
CONECT   76   75                                                            
CONECT   77   75   78   85                                                  
CONECT   78   77   68   79                                                  
CONECT   79   78   80   83                                                  
CONECT   80   79   81                                                       
CONECT   81   80   67   82                                                  
CONECT   82   81                                                            
CONECT   83   79   84                                                       
CONECT   84   83   85   87                                                  
CONECT   85   84   77   86                                                  
CONECT   86   85                                                            
CONECT   87   84                                                            
CONECT   88    1                                                            
MASTER        0    0    0    0    0    0    0    0   88    0  198    0
END

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3D PDB for NP0073750 (Squarrosanin A)
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SMILES for NP0073750 (Squarrosanin A)
OC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1COC(=O)C2=C(C(O)=C(O)C(O)=C2)C2=C(O)C(O)=C(O)C=C2C(=O)O[C@H]1[C@@H]1OC(=O)C2=C(C(O)=C(O)C(O)=C2)C2=C(O)C(O)=C(O)C3=C2C(=O)O[C@H]1[C@H]3C1=C2C(=O)OC3=C4C(C(=O)OC(C(O)=C1O)=C24)=C(O)C(O)=C3
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INCHI for NP0073750 (Squarrosanin A)
InChI=1S/C55H32O33/c56-12-1-8(2-13(57)32(12)62)49(75)84-19-7-82-50(76)9-3-14(58)34(64)37(67)20(9)21-10(4-15(59)35(65)38(21)68)51(77)85-45(19)48-47-28(26-30-27-23-18(83-53(30)79)6-17(61)33(63)31(23)55(81)86-46(27)44(74)42(26)72)25-29(54(80)87-47)24(40(70)43(73)41(25)71)22-11(52(78)88-48)5-16(60)36(66)39(22)69/h1-6,19,28,45,47-48,56-74H,7H2/t19-,28-,45-,47+,48+/m1/s1
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View in JSmol
Synonyms
ValueSource
(10R,11R)-10-[(14R,15S,19R)-2,3,4,7,8,9-Hexahydroxy-12,17-dioxo-19-{6,7,12,13-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0,.0,]hexadeca-1(15),4,6,8(16),11,13-hexaen-5-yl}-13,16-dioxatetracyclo[13.3.1.0,.0,]nonadeca-1,3,5(18),6,8,10-hexaen-14-yl]-3,4,5,17,18,19-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.0,]nonadeca-1(19),2,4,6,15,17-hexaen-11-yl 3,4,5-trihydroxybenzoic acidGenerator
Chemical FormulaC55H32O33
Average Mass1220.8280 Da
Monoisotopic Mass1220.08258 Da
IUPAC Name(10R,11R)-10-[(14R,15S,19R)-2,3,4,7,8,9-hexahydroxy-12,17-dioxo-19-{6,7,12,13-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4,6,8(16),11,13-hexaen-5-yl}-13,16-dioxatetracyclo[13.3.1.0^{5,18}.0^{6,11}]nonadeca-1(18),2,4,6(11),7,9-hexaen-14-yl]-3,4,5,17,18,19-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.0^{2,7}]nonadeca-1(15),2,4,6,16,18-hexaen-11-yl 3,4,5-trihydroxybenzoate
Traditional Name(10R,11R)-10-[(14R,15S,19R)-2,3,4,7,8,9-hexahydroxy-12,17-dioxo-19-{6,7,12,13-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4,6,8(16),11,13-hexaen-5-yl}-13,16-dioxatetracyclo[13.3.1.0^{5,18}.0^{6,11}]nonadeca-1(18),2,4,6(11),7,9-hexaen-14-yl]-3,4,5,17,18,19-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.0^{2,7}]nonadeca-1(15),2,4,6,16,18-hexaen-11-yl 3,4,5-trihydroxybenzoate
CAS Registry NumberNot Available
SMILES
OC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1COC(=O)C2=C(C(O)=C(O)C(O)=C2)C2=C(O)C(O)=C(O)C=C2C(=O)O[C@H]1[C@@H]1OC(=O)C2=C(C(O)=C(O)C(O)=C2)C2=C(O)C(O)=C(O)C3=C2C(=O)O[C@H]1[C@H]3C1=C2C(=O)OC3=C4C(C(=O)OC(C(O)=C1O)=C24)=C(O)C(O)=C3
InChI Identifier
InChI=1S/C55H32O33/c56-12-1-8(2-13(57)32(12)62)49(75)84-19-7-82-50(76)9-3-14(58)34(64)37(67)20(9)21-10(4-15(59)35(65)38(21)68)51(77)85-45(19)48-47-28(26-30-27-23-18(83-53(30)79)6-17(61)33(63)31(23)55(81)86-46(27)44(74)42(26)72)25-29(54(80)87-47)24(40(70)43(73)41(25)71)22-11(52(78)88-48)5-16(60)36(66)39(22)69/h1-6,19,28,45,47-48,56-74H,7H2/t19-,28-,45-,47+,48+/m1/s1
InChI KeyNCKJEPQXUIIESS-QVWPFDLFSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Melaleuca squarrosaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassTannins  
Sub ClassHydrolyzable tannins  
Direct ParentHydrolyzable tannins  
Alternative Parents
Substituents
  • Hydrolyzable tannin
    • 

  • Pentacarboxylic acid or derivatives
    • 

  • Galloyl ester
    • 

  • 7,8-dihydroxycoumarin
    • 

  • 6,7-dihydroxycoumarin
    • 

  • Gallic acid or derivatives
    • 

  • P-hydroxybenzoic acid alkyl ester
    • 

  • M-hydroxybenzoic acid ester
    • 

  • P-hydroxybenzoic acid ester
    • 

  • Isocoumarin
    • 

  • Coumarin
    • 

  • 2-benzopyran
    • 

  • 1-benzopyran
    • 

  • Isochromane
    • 

  • Benzopyran
    • 

  • Benzoate ester
    • 

  • Pyrogallol derivative
    • 

  • Benzoic acid or derivatives
    • 

  • Benzenetriol
    • 

  • Benzoyl
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • Phenol
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Monocyclic benzene moiety
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.55ALOGPS
logP5.31ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)5.61ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count26ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area568.47 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity281.52 m³·mol⁻¹ChemAxon
Polarizability106.54 ųChemAxon
Number of Rings12ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound163105164  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References