NP-MRD: Showing NP-Card for Squarrosanin B (NP0073751)

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Record Information

Version

2.0

Created at

2022-04-28 18:58:35 UTC

Updated at

2022-04-28 18:58:35 UTC

NP-MRD ID

NP0073751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Squarrosanin B

Description

(10R,11S)-3,4,5,17,18,19-hexahydroxy-8,14-dioxo-10-[(1S,2S,3R)-1,2,3-trihydroxy-3-{6,7,12,13-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]Hexadeca-1(15),4(16),5,7,11,13-hexaen-5-yl}propyl]-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 B is found in Melaleuca squarrosa. Based on a literature review very few articles have been published on (10R,11S)-3,4,5,17,18,19-hexahydroxy-8,14-dioxo-10-[(1S,2S,3R)-1,2,3-trihydroxy-3-{6,7,12,13-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]Hexadeca-1(15),4(16),5,7,11,13-hexaen-5-yl}propyl]-9,13-dioxatricyclo[13.4.0.0²,⁷]Nonadeca-1(19),2,4,6,15,17-hexaen-11-yl 3,4,5-trihydroxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220582D          

 67 74  0  0  1  0            999 V2000
    9.2705    6.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9937    6.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0117    5.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3063    5.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5830    5.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5651    6.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8419    6.8811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8777    5.2315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4217    5.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9096    6.4752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4527    4.3813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2775    4.3992    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7458    5.1711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2649    4.5299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0798    4.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3754    5.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5990    4.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4138    4.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9330    3.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6373    2.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8225    2.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3033    3.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5268    1.8363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1565    2.0944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7478    3.6348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5247    5.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5067    6.2678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7168    6.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2259    5.8425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2154    7.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3906    7.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9627    7.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3596    8.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1844    8.6850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6123    7.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5813    9.4083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9317    9.3725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1379    7.9259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6900    3.6847    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2775    2.9703    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4525    2.9703    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0400    2.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2150    2.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8025    1.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2150    0.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0400    0.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4525    1.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2775    1.5413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4525    0.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8025    0.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9775    0.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5650   -0.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5650    0.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9775    1.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5650    2.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9775    2.9703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8025    2.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2150    3.6847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7400    2.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3275    1.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7400    0.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3275    0.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5025    1.5413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0400    3.6847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6900    2.2558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5150    3.6847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7712    7.5689    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
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 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
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 21 23  1  0  0  0  0
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 19 25  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  0  0  0  0
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 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
  2 31  1  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
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 12 39  1  1  0  0  0
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 51 52  2  0  0  0  0
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 53 54  1  0  0  0  0
 44 54  1  0  0  0  0
 54 55  2  0  0  0  0
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 43 57  1  0  0  0  0
 57 58  2  0  0  0  0
 55 59  1  0  0  0  0
 59 60  2  0  0  0  0
 60 61  1  0  0  0  0
 53 61  2  0  0  0  0
 61 62  1  0  0  0  0
 60 63  1  0  0  0  0
 41 64  1  1  0  0  0
 40 65  1  1  0  0  0
 39 66  1  1  0  0  0
  1 67  1  0  0  0  0
M  END

     RDKit          3D

 95102  0  0  0  0  0  0  0  0999 V2000
    2.3099    4.0616   -1.9956 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2788    3.9648   -0.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1890    2.6769   -0.2584 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1304    1.5668   -1.0924 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5588    0.8926   -1.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5058    0.1898    0.1395 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4944   -0.4966    0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9444    0.1092    1.8929 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0999   -1.7791    0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4997   -1.6710    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2803   -2.7594    0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6618   -2.5429   -0.1721 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6973   -3.9827   -0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4880   -5.1047   -0.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3430   -4.1107    0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8582   -5.4208    0.0192 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4934   -3.0173    0.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6386   -4.5894    1.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5815   -5.1688    1.6073 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1744    0.4411   -1.0173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6802   -0.7379   -0.4107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9330    1.6563   -0.6038 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3884    2.6662   -1.4976 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.4710   -2.9860    0.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4157   -1.6644   -3.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
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 48 88  1  0
 50 89  1  0
 51 90  1  0
M  END


  Mrv1652304282220582D          

 67 74  0  0  1  0            999 V2000
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    9.9937    6.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0117    5.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3063    5.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.4525    0.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8025    0.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9775    0.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5650   -0.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5650    0.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9775    1.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5650    2.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9775    2.9703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8025    2.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2150    3.6847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7400    2.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3275    1.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7400    0.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3275    0.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5025    1.5413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 41 64  1  1  0  0  0
 40 65  1  1  0  0  0
 39 66  1  1  0  0  0
  1 67  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]([C@H](O)[C@H]1OC(=O)C2=CC(O)=C(O)C(O)=C2C2=C(C=C(O)C(O)=C2O)C(=O)OC[C@@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1)[C@H](O)C1=C2C(=O)OC3=C4C(C(=O)OC(C(O)=C1O)=C24)=C(O)C(O)=C3

> <INCHI_IDENTIFIER>
InChI=1S/C41H28O26/c42-10-1-7(2-11(43)24(10)47)37(58)65-16-6-63-38(59)8-3-12(44)26(49)28(51)17(8)18-9(4-13(45)27(50)29(18)52)39(60)66-35(16)34(57)32(55)30(53)22-21-20-19-15(64-40(21)61)5-14(46)25(48)23(19)41(62)67-36(20)33(56)31(22)54/h1-5,16,30,32,34-35,42-57H,6H2/t16-,30+,32-,34-,35-/m0/s1

> <INCHI_KEY>
PQROAZRZUSLDJS-BFMPKQKFSA-N

> <FORMULA>
C41H28O26

> <MOLECULAR_WEIGHT>
936.649

> <EXACT_MASS>
936.086881022

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
82.15191886880828

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
16

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10R,11S)-3,4,5,17,18,19-hexahydroxy-8,14-dioxo-10-[(1S,2S,3R)-1,2,3-trihydroxy-3-{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}propyl]-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>
2.78

> <JCHEM_LOGP>
2.4246891376666664

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
7.471109576258764

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.206598447113181

> <JCHEM_PKA_STRONGEST_BASIC>
-4.601632420321246

> <JCHEM_POLAR_SURFACE_AREA>
455.1800000000001

> <JCHEM_REFRACTIVITY>
213.60830000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10R,11S)-3,4,5,17,18,19-hexahydroxy-8,14-dioxo-10-[(1S,2S,3R)-1,2,3-trihydroxy-3-{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}propyl]-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

$$$$

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      17.305  12.903   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.655  12.162   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.688  10.622   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.372   9.823   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.022  10.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.988  12.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.638  12.845   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      14.705   9.765   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      19.454  10.845   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      20.365  12.087   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      19.512   8.178   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      21.051   8.212   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.925   9.653   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      22.895   8.456   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      24.416   8.697   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      24.967  10.134   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      25.385   7.500   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.906   7.741   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.875   6.544   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.323   5.106   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.802   4.865   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.833   6.062   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      25.250   3.428   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      28.292   3.909   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      29.396   6.785   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      23.379  10.160   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      23.346  11.700   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      21.871  12.144   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      20.955  10.906   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      20.935  13.545   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.396  13.512   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      18.597  14.829   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      19.338  16.179   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      20.878  16.212   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      21.676  14.895   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      21.618  17.562   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      18.539  17.495   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      17.057  14.795   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      21.821   6.878   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      21.051   5.544   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      19.511   5.544   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      18.741   4.211   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      17.201   4.211   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      16.431   2.877   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      17.201   1.543   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      18.741   1.543   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      19.511   2.877   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      21.051   2.877   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      19.511   0.210   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      16.431   0.210   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      14.891   0.210   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      14.121  -1.124   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      14.121   1.543   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      14.891   2.877   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      14.121   4.211   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      14.891   5.544   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      16.431   5.544   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      17.201   6.878   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      12.581   4.211   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      11.811   2.877   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      12.581   1.543   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      11.811   0.210   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      10.271   2.877   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      18.741   6.878   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      21.821   4.211   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      23.361   6.878   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      16.373  14.129   0.000  0.00  0.00           O+0
CONECT    1    2    6   67                                                  
CONECT    2    1    3   31                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    3   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   39                                                  
CONECT   13   12   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   17                                                       
CONECT   23   21                                                            
CONECT   24   20                                                            
CONECT   25   19                                                            
CONECT   26   13   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   35                                                  
CONECT   31   30    2   32                                                  
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   12   40   66                                                  
CONECT   40   39   41   65                                                  
CONECT   41   40   42   64                                                  
CONECT   42   41   43   47                                                  
CONECT   43   42   44   57                                                  
CONECT   44   43   45   54                                                  
CONECT   45   44   46   50                                                  
CONECT   46   45   47   49                                                  
CONECT   47   46   42   48                                                  
CONECT   48   47                                                            
CONECT   49   46                                                            
CONECT   50   45   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54   61                                                  
CONECT   54   53   44   55                                                  
CONECT   55   54   56   59                                                  
CONECT   56   55   57                                                       
CONECT   57   56   43   58                                                  
CONECT   58   57                                                            
CONECT   59   55   60                                                       
CONECT   60   59   61   63                                                  
CONECT   61   60   53   62                                                  
CONECT   62   61                                                            
CONECT   63   60                                                            
CONECT   64   41                                                            
CONECT   65   40                                                            
CONECT   66   39                                                            
CONECT   67    1                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  148    0
END

View in JSmol

Synonyms

Value	Source
(10R,11S)-3,4,5,17,18,19-Hexahydroxy-8,14-dioxo-10-[(1S,2S,3R)-1,2,3-trihydroxy-3-{6,7,12,13-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0,.0,]hexadeca-1(15),4(16),5,7,11,13-hexaen-5-yl}propyl]-9,13-dioxatricyclo[13.4.0.0,]nonadeca-1(19),2,4,6,15,17-hexaen-11-yl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₄₁H₂₈O₂₆

Average Mass

936.6490 Da

Monoisotopic Mass

936.08688 Da

IUPAC Name

(10R,11S)-3,4,5,17,18,19-hexahydroxy-8,14-dioxo-10-[(1S,2S,3R)-1,2,3-trihydroxy-3-{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}propyl]-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

CAS Registry Number

Not Available

SMILES

O[C@H]([C@H](O)[C@H]1OC(=O)C2=CC(O)=C(O)C(O)=C2C2=C(C=C(O)C(O)=C2O)C(=O)OC[C@@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1)[C@H](O)C1=C2C(=O)OC3=C4C(C(=O)OC(C(O)=C1O)=C24)=C(O)C(O)=C3

InChI Identifier

InChI=1S/C41H28O26/c42-10-1-7(2-11(43)24(10)47)37(58)65-16-6-63-38(59)8-3-12(44)26(49)28(51)17(8)18-9(4-13(45)27(50)29(18)52)39(60)66-35(16)34(57)32(55)30(53)22-21-20-19-15(64-40(21)61)5-14(46)25(48)23(19)41(62)67-36(20)33(56)31(22)54/h1-5,16,30,32,34-35,42-57H,6H2/t16-,30+,32-,34-,35-/m0/s1

InChI Key

PQROAZRZUSLDJS-BFMPKQKFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melaleuca squarrosa	Plant	KNApSAcK

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
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
Benzopyran
Benzoate ester
Tricarboxylic acid or derivatives
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
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.78	ALOGPS
logP	2.42	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	6.21	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	16	ChemAxon
Polar Surface Area	455.18 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	213.61 m³·mol⁻¹	ChemAxon
Polarizability	82.15 Å³	ChemAxon
Number of Rings	8	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

163188472

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Squarrosanin B (NP0073751)

MOL for NP0073751 (Squarrosanin B)

3D MOL for NP0073751 (Squarrosanin B)

3D SDF for NP0073751 (Squarrosanin B)

3D-SDF for NP0073751 (Squarrosanin B)

PDB for NP0073751 (Squarrosanin B)

3D PDB for NP0073751 (Squarrosanin B)

SMILES for NP0073751 (Squarrosanin B)

INCHI for NP0073751 (Squarrosanin B)

Structure for NP0073751 (Squarrosanin B)

3D Structure for NP0073751 (Squarrosanin B)